the amino acid and monosaccharide content of the cell

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Scholars' Mine Scholars' Mine Doctoral Dissertations Student Theses and Dissertations 1967 The amino acid and monosaccharide content of the cell walls of The amino acid and monosaccharide content of the cell walls of Thiobacillus thiooxidans Thiobacillus thiooxidans Edward Hibbert Crum Follow this and additional works at: https://scholarsmine.mst.edu/doctoral_dissertations Part of the Chemical Engineering Commons Department: Chemical and Biochemical Engineering Department: Chemical and Biochemical Engineering Recommended Citation Recommended Citation Crum, Edward Hibbert, "The amino acid and monosaccharide content of the cell walls of Thiobacillus thiooxidans" (1967). Doctoral Dissertations. 1874. https://scholarsmine.mst.edu/doctoral_dissertations/1874 This thesis is brought to you by Scholars' Mine, a service of the Missouri S&T Library and Learning Resources. This work is protected by U. S. Copyright Law. Unauthorized use including reproduction for redistribution requires the permission of the copyright holder. For more information, please contact [email protected].

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Page 1: The amino acid and monosaccharide content of the cell

Scholars' Mine Scholars' Mine

Doctoral Dissertations Student Theses and Dissertations

1967

The amino acid and monosaccharide content of the cell walls of The amino acid and monosaccharide content of the cell walls of

Thiobacillus thiooxidans Thiobacillus thiooxidans

Edward Hibbert Crum

Follow this and additional works at: https://scholarsmine.mst.edu/doctoral_dissertations

Part of the Chemical Engineering Commons

Department: Chemical and Biochemical Engineering Department: Chemical and Biochemical Engineering

Recommended Citation Recommended Citation Crum, Edward Hibbert, "The amino acid and monosaccharide content of the cell walls of Thiobacillus thiooxidans" (1967). Doctoral Dissertations. 1874. https://scholarsmine.mst.edu/doctoral_dissertations/1874

This thesis is brought to you by Scholars' Mine, a service of the Missouri S&T Library and Learning Resources. This work is protected by U. S. Copyright Law. Unauthorized use including reproduction for redistribution requires the permission of the copyright holder. For more information, please contact [email protected].

Page 2: The amino acid and monosaccharide content of the cell

THE AMINO ACID AND MONOSACCHARIDE CONTENT OF THE CELL

WALLS OF THIOBACILLUS THIOOXIDANS

by

EDWARD HIBBERT CRUM -· / <i ... · '

A DISSERTATION

Presented to the Faculty of the Graduate School of the

UNIVERSITY OF MISSOURI AT ROLLA

In Partial Fulfillment of the Requirements for the Degree

DOCTOR OF PHILOSOPHY

1967

. I

/' '

~-~~~---: I

Page 3: The amino acid and monosaccharide content of the cell

THE AMINO ACID AND MONOSACCHARIDE CONTENT

OF THE CELL WALLS OF THIOBACILLUS THIOOXIDANS

By: Edward Hibbert Crum Advisor: Dr. Donald J. Siehr

ABSTRACT

The objectives of this investigation were: (a) to

ii

culture large quantities of Thiobacillus thiooxidans cells,

(b) to find an acceptable method of rupturing the cells,

(c) to find an acceptable method of isolating the cell walls,

and (d) to analyze the cell wall components, especially the

amino acid and sugar components. The strain of T. thiooxidans

used for this investigation was American Type Culture Col-

lection Number 8085.

The surface active agents Tergitol 08* and Tween 80**

were investigated for their ability to reduce the lag period

found in the growth of T. thiooxidans. Although a concentra-

tion of 12.5 ppm Tween 80 did decrease the lag period, the

use of these surfactants was not effective in increasing the

amount of cells grown over a specific time period because

they reduced the cell yield.

Two cell rupture techniques, sonication and pressure

cell rupture, coupled with either washing with deionized

Edward H. Crum

*Union Carbide Corp. Registered Trademark.

**Atlas Chemical Industry Registered Trademark.

Page 4: The amino acid and monosaccharide content of the cell

iii

water or washing and treatment with IR-120* and AG-1X2* ion

exchange resins, were tested. The cell walls were also

ruptured in both deionized water and deionized water

buffered at pH 7.9. The release of soluble nitrogen was

used as a measure of the effectiveness of cell rupture. The

best rupture of T. thiooxidans was obtained by washing the

cells with deionized water, followed by pressure cell rupture

in the basic buffer solution. The procedure solubilized

68% of the total nitr~gen present.

The cell walls were isolated and purified by a combina-

tion of differential centrifugation, linear sucrose gradient

centrifugation, and washing. The cell walls were hydrolyzed

in sealed tubes at 100 to 120 C with hydrochloric acid,

sulfuric acid, and the ion exchange resin IR-120 as catalysts.

In the study of the amino acids in cell walls, the walls

were also digested with trypsin, washed, and then hydrolyzed

with hydrochloric acid in a sealed tube. The cell wall

hydrolyzates were separated by two dimensional paper

chromatography for a qualitative estimation of the amino

acids present in the cell walls. A quantitative determina-

tion of the amino acids in the cell wall hydrolyzates was

obtained by the use of an Amino Acid Analyzer.

The cell wall of T. thiooxidans was found to have an

amino acid content qualitatively and quantitatively more

*Obtained from Bio-Rad., 32nd and Griffin Streets, Richmond, Calif.

Edward H. Crum

Page 5: The amino acid and monosaccharide content of the cell

like that of Gr~m-negative than Gram-positive bacteria.

Evidence that ornithine was present in the cell walls was

obtained. The ornithine might possibly have been an

artifact formed during the rupture procedure.

Hydrolysis of the cell walls in sulfuric acid failed

to liberate monosaccharides. Therefore, hydrolysis of the

cell walls in the presence of IR-120 was used for qualita­

tive determination of the monosaccharides present in the

iv

cell wall. Paper chromatography of the cell wall hydrolyzates

indicated the presence of rhamnose, glucose, and galactose.

The hydrolyzates also contained small amounts of the amino

sugar glucosamine. Since the resolution of glucose and

galactose was not good on papergrams, the monosaccharide

mixture was treated with glucose oxidase before chromatography.

The gluconic acid formed with this treatment was nicely

separated from the galactose.

Since the cell walls of T. thiooxidans enables the

bacterium to survive in very acidic media, knowledge of the

cell wall composition has implications in the control of acid

mine drainage by providing a rational approach to the pre­

vention of the growth of this organism.

Edward H. Crum

Page 6: The amino acid and monosaccharide content of the cell

TITLE PAGE

ABSTRACT . .

TABLE OF CONTENTS

. . . . . . . . . . . . . . . . . . . . . . . . . .

. . .

TABLE OF CONTENTS

LIST OF FIGURES

. . . . . . . . . . . . . . . . . . . . . . . . . . . . .

LIST OF TABLES . . • . . . . . . . . . . I. INTRODUCTION ... . . . . . . .

II. LITERATURE REVIEW .. . . . . . .

III.

A.

B.

THIOBACILLUS THIOOXIDANS

THE BACTERIAL CELL WALL .

. . . . . .

EXPERIMENTAL . . . . . . . . . • . . .

A. MATERIALS AND METHODS . . . . • . . .

1. Cultivation of Cells ...•...

2. Preparation of Cell Walls .

. . .

. . .

. . .

v

Page

~

ii

v

vii

ix

1

6

6

18

41

41

41

44

3. Cell Wall Components. . . . . . . . . . 50

B.

4. Protein and Nitrogen Determinations 54

5. Surfactant Studies . . . . . . . . . . 57

RESULTS . . • . . . . . . . .

1. Surfactant Studies .•..

2. Cell Rupture .•....••...

3. Paper Chromatography ...... .

. . . 59

59

64

64

4. Amino Acid Analysis . . . • . . . . . . 6 8

5. Test for Contamination •.. . . . . 68

Page 7: The amino acid and monosaccharide content of the cell

vi

Page

IV. DISCUSSION . . . . . . . . . . . . . . . . . . . 72

A. DISCUSSION OF RESULTS . . . . . . . . . . . 72

1. Surfactant Studies . . . . . . . 72

2. Cell Rupture . . . . . . . . . . . . . . 74

3. Hydrolysis Methods . . . . . . . . . . . 76

4. Analysis of Cell Walls . . . . . . . . . 77

5. Test for Contamination . . . . . . . . . 87

B. LIMITATIONS. . . . . . . . . . . . . . . . . 88

v. CONCLUSIONS. . . . . . . . . . . . . . . 90

VI. RECOMMENDATIONS . . . . . . . . . . . . . . . . 91

VII. BIBLIOGRAPHY . . . . . . . . . . . . . . 92

VIII. ACKNOWLEDGEMENT. . . . . . . . . . . . . . . 101

IX. VITA . . . . . . . . . . . . . . . . . . . . 102

Page 8: The amino acid and monosaccharide content of the cell

Figure 1.

Figure 2.

Figure 3.

Figure 4.

Figure 5.

Figure 6.

Figure 7.

vii

LIST OF FIGURES

Page

Proposed Scheme of Carbon Dioxide Fixation by Thiobacillus thiooxidans (56) . . . 14

Chemical Composition of Bacterial Cell Walls. . . . . . . . . . . . . . . 20

Diagrammatic Representation of Cell Walls (29, p. 23) . . . . . • . . . . . . . . . 21

Structures of a- E Diaminopimelic Acid and Muramic Acid (76, 77, 78)....... 24

The Proposed Structure of Amino Sugar, Di-and-Tetrasaccharides from Micrococcus lysodeikticus (82) . . • . . • . . . . . . 26

Type of Molecular Structure Proposed for the Cell Wall of Micrococcus l;'isodeikticus ( 8 3) . . . . . . . . . . . . . . . 27

Structure of a "Park Nucleotide" from StaEh~lococcus aureus (25) . . . . . . 29

Figure 8. Structure of Two Glycosaminopeptides Isolated from Escherichia coli Cell Walls (88) . . . . . . . . . . . . . . . . . 31

Figure 9. Hypothetical Glycosaminopeptide Subunit of the Cell Wall of Micrococcus lysodeikticus (86) • • • . • • • • . . • • . . • 32

Figure 10. Hypothetical Subunit of the Cell Wall of Aerobacter cloacae (29, 147) . . . . • . . 33

Figure 11.

Figure 12.

Figure 13.

Figure 14.

Four General Types of Teichoic Acid (29' p. 159) . • . . . • . . ..

Proposed Structure of Cell Walls of Staphylococcus aureus (89) ..•

General Scheme for Differential Centri­fugation (29, po 58) . o •• o o •••

Sketch of Fermentation Apparatus (91)

Figure 15. Device Used to Produce Linear Sucrose Gradients o . o • • o o o • • • • • •

34

35

0 • 39

0 0 43

47

Page 9: The amino acid and monosaccharide content of the cell

Figure 16. Layers Formed During Linear Sucrose Gradient Purification . • . • • • . . . .

Figure 17. The Effect of Surfactant Tween 80 on the Growth of Thiobacillus thiooxidans.

viii

Page

49

Shake Flask Studies • . • . • . . • • • • 61

Figure 18. The Effect of Surfactant Tween 80 on the Growth of Thiobacillus thiooxidans. Shake Flask Studies • . . . • . . . . • . 62

Figure 19. The Effect of Surfactant Tween 80 on the Growth of Thiobacillus thiooxidans• Fermentor Studies . . • . . • . • • • . . 65

Figure 20. Ultraviolet Absorption of Cell Walls and Supernatant from Pressure Cell Rupture. . 71

Page 10: The amino acid and monosaccharide content of the cell

ix

LIST OF TABLES

Page

Table 1. Principal Classes of Chemicals Found in Cell Walls of Bacteria (29, p. 251) . . 23

Table 2. The Effect of Surfactant Tween 80 on the Growth of Thiobacillus thiooxidans. Shake Flask Stud~es . . . . . . . . . . • . 60

Table 3. The Effect of Surfactant Tween 80 on the Growth of Thiobacillus thiooxidans. Fermentor Stud~es . . . . . . . . . . • • . 63

Table 4. Thiobacillus thiooxidans Cell Rupture Experiments . . . • . . . . . . . . . . . .

Table 5.

Table 6.

The Qualitative Amino Acid Content of Thiobacillus thiooxidans Cell Walls . .

The Quantitative Amino Acid Content of Thiobacillus thiooxidans Cell Walls

Table 7. The Qualitative Amino Acid Content of Some Gram-positive and Gram-negative

. .

. .

66

69

70

Bacterial Cell Walls ( 9 5) • . • . . . . 79

Table 8. The Quantitative Amino Acid Content of Some Gram-positive and Gram-negative Bacterial Cell Walls (29, p. 254-255} . . . 82

Table 9. Molar Ratios of Some Amino Acids in Cell Walls . . . . . . . . . . . . . . . . . . . 84

Page 11: The amino acid and monosaccharide content of the cell

I. INTRODUCTION

With the advent of state and federal regulations regard­

ing water pollution one serious problem of concern in the

Appalachian region is that of acid mine drainage. While

microorganisms may not be completely responsible for this

acid drainage, they act to speed the production of acid (1).

The organism Thiobacillus thiooxidans is generally found in

acid mine water. This fact is substantiated by the statement

of Temple and Colmer (2). "A survey of acid mine waters of

the Morgantown area, from other parts of the state [W. Va.]

and from Pennsylvania showed that Thiobacillus thiooxidans

is present 1n all the acid mine waters examined and may

reasonably be supposed to be in all acid mine waters." Many

other investigators have linked T. thiooxidans, as well as a

very similar organism Thiobacillus ferrooxidans, with acid

mine drainage or acid formation from pyrites in the soil (1,

3-17) .

In a survey made of the streams in West Virginia, it has

been estimated that an average of 168,349,000 gallons of mine

drainage containing the equivalent of 2,876,000 pounds of

concentrated sulfuric acid were daily flowing into the river

systems of the state (18). The total sulfuric acid equiva­

lent for the Ohio River Basin was estimated at around

2,500,000 tons per year during the 1942 Ohio River Pollution

Survey (19).

The damage caused by acid mine drainage to navigational

and floating equipment in the Pittsburgh area was estimated

Page 12: The amino acid and monosaccharide content of the cell

in 1926 by the U. S. War Department at 500,000 to 600,000

dollars per year (20). In 1942 the Works Progress

Administration made a conservative estimate of the extra

costs due to damage by acid mine drainage in the states of

the Ohio River Basin, and placed these costs at about

10,000,000 dollars per year (19).

2

Braley (1) recently reported that four methods are cur­

rently used to treat or prevent acid mine drainage: (a) mine

sealing, (b) neutralization of the acid, (c) pickup system,

and (d) subsurface disposal of acid mine water.

The first method can be used with abandoned mines only,

while the last three are basically directed toward use in

operating mines, but could be used at abandoned mines.

According to Braley (1) , mine sealing has not been as

effective as originally expected because of "breathing''. He

explained that "breathing" occurs because of the natural

porosity of geological formations and fractures induced in

the strata above the coal.

Neutralization of the acid mine drainage was tried

during World War I by the Frick Coal Company. The project

was abandoned after the war as economically unfeasible (1).

The Sanitary Water Board of the Commonwealth of Pennsylvania

came to the same conclusion in 1951 (1). However, the

Commonwealth of Pennsylvania is now conducting an experiment

known as "Operation Yellow-boy" to study the feasibility of

neutralization of acid mine drainage. The most recent

report (21) states that it costs 1.09 dollars per thousand

Page 13: The amino acid and monosaccharide content of the cell

3

gallons to treat acid mine drainage. This estimate was based

on data taken from a 240,000 gallon per day pilot plant, and

did not include additional expenditures for sludge processing.

Braley (1) has described a pickup system in which water

is picked up at the point of entry into the mine and trans­

ported through pipes to the exterior of the mine. This

prevents the water from carrying away any acid formed. This

method has been reported as a success. Braley, however, did

not indicate the cost of such an operation.

Linden and Stefanko (22) have described some of the

problems which must be overcome in order to make subsurface

disposal possible. Some of these are: (a) the bacteria

present in the waste must be killed, (b) dissolved gases

must be removed, (c) suspended particles must be removed,

and (d) an exacting geological survey must be made before the

well is drilled. Linden and Stefanko have not experimentally

tried subsurface disposal, therefore cost data is not avail­

able.

There are problems associated with each of the above

mentioned methods .. Sealing of a mine is applicable where

"breathing" is not a problem. Sealing would not, however,

solve the acid drainage problem of operating mines. Neutrali­

zation is very expensive and causes another problem, disposal

of the sludge formed. The pickup system, while applicable to

operating mines, would not be effective in abandoned mines.

Subsurface disposal requires extensive treatment of the waste

before ultimate injection.

Page 14: The amino acid and monosaccharide content of the cell

All the methods discussed above, except mine sealing,

are directed toward destroying or otherwise treating the

acid after it has been formed. The author feels that a

better approach would be to eliminate the production of

acid. Prevention of the growth of the microorganisms

responsible for the formation of the acid seems to be a

reasonable solution to the problem. This could be done by

spraying the mine surface with a substance which would

prevent the growth of the microorganisms.

4

The organism T. thiooxidans can live in solutions with

a very high acid concentration. The enzymes of T. thiooxi­

dans, however, operate at nearly neutral conditions. This

indicates that the cell wall has some method for maintaining

the internal pH. T. thiooxidans can also utilize sulfur as

an energy source. Since sulfur is insoluble in water the

organism has some method for transporting the sulfur across

the cell wall. It is known that the action of penicillin is

directed toward the inhibition of bacterial cell wall

synthesis (23-28; 29, p. 15, 88, and 203-216). The

penicillin inhibits the formation of glycosaminopeptides.

A knowledge of the cell wall of T. thiooxidans may help in

selecting an inhibitor of cell wall synthesis or a chemical

which would modify the function of the cell wall and either

destroy its pH maintenance system or its sulfur transport

system.

The purpose of this work was: (a) to culture large

quantities of T. thiooxidans cells, (b) to find an acceptable

Page 15: The amino acid and monosaccharide content of the cell

method of rupturing the cells, (c) to find an acceptable

method of isolating the cell walls, and (d) to analyze the

cell wall components, especially the amino acid and sugar

components.

5

Page 16: The amino acid and monosaccharide content of the cell

6

II. LITERATURE REVIEW

This literature review is divided into two parts. The

first section relates background material concerning

Thiobacillus thiooxidans, the organism under study; the

second section deals with the bacterial cell wall and its

preparation for analysis.

A. THIOBACILLUS THIOOXIDANS

The organism under study, T. thiooxidans, has been

classified in Bergey's Manual of Determinative Bacteriology

(30) in the following manner:

CLASS

ORDER

FAMILY

TRIBE

~NW

SPECIES

SCHIZOMYCETES

EUBACTERIINEAE

NITROBACTERIACEAE

THIOBACILLEAE

THIOBACILLUS

THIOOXIDANS

Waksman and Joffe (31) were the first to isolate this

organism in pure culture. They reported their findings in

1920.

T. thiooxidans organisms are short rods, 1.0 ~long

and 0.5 ~in diameter, with rounded ends. They occur singly,

in pairs, and occasionally in chains. They are motile by

means of a singular polar flagellum (30, 32) ·

Waksman and Joffe (33) have reported that the organism

is Gram-positive, while starkey (34) has reported that it

is Gram-negative. Umbreit, vogel, and Vogler (35) explained

Page 17: The amino acid and monosaccharide content of the cell

that this phenomenon was due to the conditions under which

the cells were stained; under acid conditions the organisms

reacted as Gram-positive, while under alkaline conditions

the organisms were found to be Gram-negative.

7

T. thiooxidans is autotrophic (30). By autotrophic, it

is meant that it has the ability to live and multiply in an

environment containing carbon dioxide as the sole source of

carbon; however, other sources of nutrients are required for

growth. Waksman and Joffe (33) gave the mineral require­

ments for T. thiooxidans as mere traces of potassium,

magnesium, calcium, iron, and phosphorus. A nitrogen source

was also required for growth.

Carbon added in the form of carbonates was found to

inhibit growth, because it made the medium alkaline (33).

Bicarbonates in small amounts were found to support growth.

However, the presence of bicarbonates did not give a better

growth than that observed in samples incubated under the

same conditions without them (33). No organic compound has

been found which can substitute for carbon dioxide (36).

Starkey (37) has shown, however, that glucose may enter

into the metabolism of the cell in the presence of sulfur,

but glucose would not support the growth of the organisms

without the presence of sulfur. Starkey also found citric

acid in concentrations of 5% or higher inhibitive, while at

a 2.5% concentration growth was active. Butler and

Urnbreit (38) have shown the following compounds to be

absorbed by T. thiooxidans: acetate, glycerol, D-glucose,

Page 18: The amino acid and monosaccharide content of the cell

glycine, DL-alanine, DL-aspartic acid, and DL-Proline.

Succinic acid, however, was not absorbed by T. thiooxidans.

Waksman and Joffe (33) found that glycerol, alcohol, man­

nitol, and glucose acted as stimulants for growth. O'Kane

(39) has established the following growth factors to be

present in T. thiooxidans: nicotinic acid, pantothenic

acid, biotin, riboflavin, thiamin, and pyridoxine.

T. thiooxidans is strictly aerobic (30, 33, 37). It

obtains its nitrogen from ammonium salts. Nitrogen in the

form of nitrates has been found to be toxic. The nitrogen

of asparagine, urea, and peptone has been found to be

unavailable to this organism (30, 33, 37).

T. thiooxidans can utilize either sulfur or thiosulfate

as an energy source. Thiosulfate, however, retards growth

at concentrations between 3 and 10% (40). Waksman and

Joffe (33) reported that thiosulfate was capable of sup­

porting growth, but to a much smaller extent than sulfur.

They also stated that hydrogen sulfide was not utilized as

an energy source by this organism. In opposition to this

view, Parker and Prisk (41), Waksman and Starkey (32),

Suzuki and Werkman (42), and Waksman (43) have reported that

hydrogen sulfide can be utilized by T. thiooxidans. Prisk

and Parker (41) also presented evidence which indicates

thiosulfate becomes toxic in concentrations above 1%.

Since sulfur and thiosulfate are the two energy sources

generally used in media, it is apropos that their oxidation

be discussed. There seems to be a general agreement that

8

Page 19: The amino acid and monosaccharide content of the cell

the oxidation of sulfur takes place without the formation

of intermediates which accumulate in the medium, and that

sulfate is produced directly (15, 32, 33, 41, 44). The

reaction may be represented as follows:

Agreement as to the oxidation of thiosulfate is, however, a

different matter. Two reports indicated that no intermedi­

ates were found (32, 43). The following equation was given

for the reaction:

Suzuki and Werkman (42) have reported polythionates as

intermediates in the oxidation of thiosulfate. Prisk and

Parker (41) have reported tetrathionate as an intermediate

and gave the following two-step reaction to explain their

findings:

6Na2s 2o3 + 50 2 4Na2so 4 + 2Na2s 4o6

In trying to explain these conflicting reports, Prisk and

Parker (41) suggested that the discrepancy may have come

about because of different sampling techniques. They found

that tetrathionate was only present during the 24 hour

9

period between the fifth and sixth day of incubation. They

noted that most of the other authors had taken their initial

samples after this period. Starkey(40) reported that below

a 0.5% concentration thiosulfate oxidation proceeded in a

quantitative manner to sulfates, but above this concentration

Page 20: The amino acid and monosaccharide content of the cell

sulfur precipitated due to interaction of thiosulfate with

sulfuric acid present.

The optimum temperature for growth has been reported

to be in the range of 28 to 30 c. The organism grows

slowly at 18 and 37 C. A temperature of 55 to 60 c has

been found to kill these organisms (30, 33).

10

The optimum pH for the growth of T. thiooxidans has

been reported to be in the range of 2.0 to 3.5 (33, 37, 45),

while they can grow in the range 0.5 to 6.0 (30).

Carbon dioxide fixation, endogenous respiration, and

the ability to store energy in the absence of carbon dioxide

are areas in which there is quite a bit of disagreement.

Vogler (46) has reported an endogenous respiration quotient

a0 (N) (microliters of oxygen per milligram of bacterial 2

nitrogen) of 10 to 40. This indicates one of two possibili-

ties: (a) the cells had enough unoxidized substances stored

to require 10 to 40 microliters of oxygen to oxidize it, or

(b) some cells died and lysed; these lysed products were

then absorbed by other cells and oxidized.

Vogler (47) has reported that T. thiooxidans could

oxidize sulfur in the absence of carbon dioxide and store in

the cell, energy which could be used for carbon dioxide fixa­

tion when sulfur oxidation was impossible. In the same

study it was observed that carbon dioxide was taken up under

anaerobic conditions by young cells. The young cells (7 day

incubation) were able to fix up to 40 microliters of carbon

dioxide per 100 micrograms of bacterial nitrogen without the

Page 21: The amino acid and monosaccharide content of the cell

presence of sulfur. Older cells (14 day incubation) gave

off carbon dioxide in the absence of sulfur.

11

Vogler and Umbreit (48) reported that in the absence

of carbon dioxide, phosphate was transferred into the cells

when sulfur was oxidized. In the presence of carbon

dioxide and absence of sulfur the cells fixed carbon

dioxide and excreted phosphate back into the medium. The

authors suggested a link between sulfur oxidation and the

formation of phosphate esters, which in turn was linked

to carbon dioxide fixation.

Along the same lines, LePage (49) has reported that a

polysaccharide was formed and stored during sulfur oxida­

tion. He suggested that the degradation of this polysac­

charide was the source of carbon dioxide during endogenous

respiration. He also found a release of phosphate during

endogenous respiration. The chemical composition of this

polysaccharide was given as follows:

Carbon 43.25%

Hydrogen 7.86%

Oxygen 49.89%

Phosphorus 0.68 to 1.65%

Nitrogen 0.82%

LePage and Umbreit (50) have reported that fructose

-1, 6-diphosphate, phosphoglyceric acid, fructose-6-

phosphate, glucose-6-phosphate, and glucose-1-phosphate

were other phosphorylated compounds found in T. thiooxidans.

LePage and Umbreit (51) later reported the occurrence of

Page 22: The amino acid and monosaccharide content of the cell

12

adenosine-3'-triphosphate in T. thiooxidans. This is an

unusual type of adenosine triphosphate and has not been

found in other organisms. Barker and Kornberg (52) found

no evidence of adenosine-3' or 2'-triphosphate in the cells

of T. thiooxidans.

Baalsrud and Baalsrud (53) using manometric techniques

have been unable to find carbon dioxide assimilation in the

absence of an energy source. They also reported results

which showed that phosphate was returned to the medium when

a cell suspension was not exposed to carbon dioxide. This

tends to invalidate the data presented by Vogler and

Umbreit (48).

On reexamination of previous experiments using radio-

active isotopes, Urnbreit (54) found, that sulfur oxidation

in the absence of carbon dioxide permitted cells to fix

carbon dioxide under anaerobic conditions. He also reported

the amount of carbon dioxide fixed was proportional to the

amount of sulfur previously oxidized. He reported the

release of phosphates when carbon dioxide was applied

anaerobically.

. 32 14 Newburgh (55), us1ng P and C 02 , reported results

which agreed in part with both the Baalsrud and Urnbreit

school of thought. He found carbon dioxide to be fixed by

the cells in the absence of sulfur, very little difference

in aerobic and anaerobic carbon dioxide fixations, and no

release of phosphate during carbon dioxide fixation. He

reported that p3 2 was taken up by the cells only when

Page 23: The amino acid and monosaccharide content of the cell

13

carbon dioxide, oxygen, and sulfur were present simultane­

ously.

Suzuki and Werkman (42, 45, 56-59) have made many

contributions to the understanding of T. thiooxidans

metabolism during their studies on carbon dioxide fixation.

They prepared cell-free extracts which in the presence of

glutathione oxidized sulfur. This was taken as evidence

for the presence of glutathione reductase in cell-free

extracts of T. thiooxidans. The glutathione reductase was

found to be similar to that present in Escherichia coli

( 60) •

In the presence of c14o2 , adenosine triphosphate and

ribose-5- phosphate cell-free extracts produced carboxyl­

labeled phosphoglyceric acid (58). This reaction was

found to require the presence of magnesium ions and the

presence of phosphoglyceric acid was evidence for the

presence of phosphoribuloseisomerase, phosphoribulokinase,

and carboxylating enzymes in the T. thiooxidans metabolic

system.

Using c14o2 labeling, Suzuki and Werkman (56) found

the first product of carbon dioxide fixation to be phospho­

glyceric acid. The enzyme phosphoenolpyruvate carboxylase

was also found to be present in T. thiooxidans by Suzuki

and Werkman (45, 57). From these findings these investiga­

tors proposed a scheme, shown in Figure 1, for carbon

dioxide fixation by T. thiooxidans (56).

Page 24: The amino acid and monosaccharide content of the cell

14

Hexose Phosphate

t *COOH *COOH *C02 Ribulose I

H-C-NH I 2

I --~---------~--H-c-oH Diphosphate

CH 20H

Serine

*COOH

I H-CNH 2

I CH2 I

b.COOH

Aspartic acid

I CH20P03H2

Phosphoglyceric acid ~

*COOH I "OP03H2

CH 2

Phosphoenolpyruvic acid t

*COOH I c=o I CH 3

Pyruvic acid

*yOOH

t=O I CH 2 I

b.COOH

Krebs Cycle

Oxalacetic acid

*CO 2

*CO 2

COOH I CH 2 I CH 2 I C=O I

b.COOH

Keto glutaric acid

COOH I IH2

CH 2

HC-NH 2

b.COOH

Glutamic acid

Figure 1. Proposed Scheme cf Carbon Dioxide Fixation by Thiobacillus thiooxidans (56).

Page 25: The amino acid and monosaccharide content of the cell

15

There has been much speculation as to the method by

which insoluble sulfur is metabolized by the cell. Umbreit,

Vogel, and Vogler {35) have proposed that sulfur is taken

into the cell by solution in fat globules located at the

ends of the cell. This theory was opposed by Knaysi (61) on

cytological grounds.

Starkey, Jones, and Frederick (62) have postulated that

sulfur was enzymatically transformed into a transportable

form at the surface of the cell. In a study of agitation

and wetting agents, they found that growth was more rapid

in agitated flasks than in static flasks. They also

reported that the wetting agents Tergitol 08* and Tween 80**

in small concentrations increased the rate of sulfur oxida­

tion.

Jones and Starkey (63) suggested that the amino acids

and polypeptides which they found in the medium wet the

sulfur and thus produced a more rapid oxidation of sulfur.

They made these observations while studying the surface

tension of the medium during the growth of T. thiooxidans.

They felt that the amino acids and polypeptides leaked out

of the actively metabolizing cells.

Vogler and Umbreit (64) have reported that T. thiooxidans

must be directly in contact with the sulfur for oxidation

to take place. In the same report the authors concluded

*Union Carbide Corp. Registered Trademark

**Atlas Chemical Industry Registered Trademark

Page 26: The amino acid and monosaccharide content of the cell

16

that it was neither necessary nor probable that T. thiooxi­

dans was able to render sulfur soluble in the medium. It

was found that surface active agents were capable of

increasing the rate of sulfur oxidation.

Schaeffer (65} has reported that 40 to 60% of the

material excreted by T. thiooxidans was a surface active

agent which he was able to extract from the medium. He

identified this material as phosphatidyl inositol. Jones

and Benson (66), however, have reported that the surfactant

was phosphatidyl glycerol and not phosphatidyl inositol.

They found no phosphatidyl inositol in either the total

cell extract or the lipid fractions. Although these results

do not agree as to the compound responsible, they do agree

on the point that a surfactant produced by T. thiooxidans

does aid in sulfur oxidation.

Reports indicate that increasing the partial pressure

of oxygen, above the medium, gave little increase in the

rate of sulfur oxidation (64, 67). Increasing the partial

pressure of carbon dioxide, however, increased the rate of

sulfur oxidation (40). Slight increases in the total

pressure also enhanced the oxidation of sulfur (40).

T. thiooxidans is of academic interest for several

reasons. The organisms are autotrophic. They must, there­

fore, synthesize all required organic material from carbon

dioxide and inorganic salts. This requires metabolic steps

not found in heterotrophic organisms and therefore they may

be different from any heretofore studied. The organism can

Page 27: The amino acid and monosaccharide content of the cell

17

by some means oxidize sulfur or certain sulfur containing

compounds to sulfuric acid and in this manner trap energy.

This energy is then used for cell growth and carbon dioxide

assimilation. This process is somewhat similar to photo­

synthesis, in that the starting and final products are

known (sulfur and sulfuric acid), but the mechanism of

trapping the energy has not been elucidated. Another inter-

esting point is the fact that this organism can grow in an

environment of very low pH while maintaining its internal

pH near neutrality. Recently Fischer et al. (68, 69) have --observed that T. thiooxidans makes an electrical contribution

to a half-cell electromotive force when actively oxidizing

sulfur. At present the voltages are small but this research

may ultimately lead to a practical biocell.

Page 28: The amino acid and monosaccharide content of the cell

18

B. THE BACTERIAL CELL WALL

The study of bacterial cell walls is not an old field.

Martin (25) indicated that for experimental purposes it

began in 1951 with a report by Salton and Horne (70) which

outlined a procedure for the isolation of cell walls on a

preparative scale.

Bacterial cell walls provide the vital bacterial

cytoplasm with a rigid, protective covering. Although the

covering provides rigidity to the bacterium, it allows for

the permeability of nutrients ranging from ions to mole­

cules with molecular weights in the millions. The cell

wall is flexible enough to allow cell division and the

rapid growth of the bacterium. For the construction of

this shape-giving framework the bacteria use materials of

complex composition whose macromolecular organization is

quite different from any known polymer.

The cell walls of bacteria are composed of the fol­

lowing basic building blocks: (a) amino acids, (b) sugars,

(c) amino sugars, (d) lipids, and (e) polyols. Two strik­

ing chemical differences have been shown to exist in the

cell wall make-up of Gram-positive and Gram-negative

organisms. The cell walls of Gram-positive organisms have

little or no lipid material (0 to 2%) , while the cell walls

of Gram-negative organisms contain as much as 20% by

weight lipid material (29, p. 126}. The cell walls of

Gram-positive organisms also were found to contain a very

Page 29: The amino acid and monosaccharide content of the cell

small number of amino acids, three or four for some, while

the Gram-negative organisms contain the whole range of

amino acids found in most protein hydrolyzates (71). The

chemical differences in the cell walls of Gram-positive

and Gram-negative organisms are represented in Figure 2.

Physically, the cell walls of Gram-positive organisms

are composed of one continuous layer bordered by the cyto­

plasmic membrane. The Gram-negative cell walls consist of

several layers which surround the cytoplasmic membrane.

Figure 3, taken from the work of Salton (29, p. 23),

graphically represents this difference.

19

The cell walls of the Gram-positive organisms were

initially thought to be one homogeneous polymer. This

polymer in the course of its identification and character­

ization has been given many names, for example, mucopeptide,

mucocomplex, mucoprotein, peptido-polysaccharide, glyco­

peptide, glycosaminiopeptide, and murein (25, 29, p. 99-100).

For lack of a uniformly acceptable nomenclature glycosa­

minopeptide will be used here. One portion of the Gram­

negative cell wall amounting to 10 to 20% by weight has

been found to be a glycosaminopeptide in nature. More

recently, other polymers have been found to be part of the

Gram-positive cell wall in certain species. A group of

polymers called the teichoic acids were discovered by

Baddiley, Buchanan, and Carss (72). Their results were

published in 1958. Another polymer, which has not been

found as generally distributed as teichoic acid, is

Page 30: The amino acid and monosaccharide content of the cell

Gram­

Posi­

tive

Gram

ega­

tive

Cytoplasmic membrane

Amino Sugars: 10-18% Glucosamine, Galactosamine, Muramic acid

20

Total Reducing Substances: 40-50% Glucose, Galactose, Mannose, Arabinose, Rhamnose

Amino Acids: 40-50% ------~Glutamic Acid, Lysine or DAP,

Alanine, Glycine, Aspartic Acid, Serine

Total Lipids: 0-2% Phosphate: 0.2-0.8% Ribitol-5'-Phosphate

Cell Wall ~~Lipo-Glycosamino­

Peptide ---------1

Cytoplasmic Membrane

Lipoprotein: 80% contains all Amino Acids

Glycosaminopeptide: 20% similar to that of Gram­positive walls

Total Lipids: 16-20%

Figure 2. Chemical Composition of Bacterial Cell Walls.

Page 31: The amino acid and monosaccharide content of the cell

21

c.w. m cyt. c.w. m cyt.

'. . -' ~ ...... . .

, , / ...

--..; .... ~ jllo

(a) (b)

Figure 3. Diagrammatic Representation of Cell Walls (29, p.23).

(a) Thick amorphous cell wall (c.w.) and underlying cyto­plasmic membrane (m) and cytoplasm (cyt.) as found in Gram-positive bacteria.

(b) Multilayered cell wall and underlying membrane as found in Gram-negative bacteria.

Page 32: The amino acid and monosaccharide content of the cell

22

teichuronic acid isolated by Janczura, Perkins, and

Rodgers (73) in 1961. Table 1 shows various groups of

substances found in the cell walls of both Gram-positive

and Gram-negative organisms. Some Gram-positive cell walls

may be comprised of 90% by weight of glycosaminopeptide

(e.g. Micrococcus lysodeikticus).

The cell walls of bacteria contain some unique chemi­

cal compounds. Three of these are D-alanine, D-aspartic

and D-glutamic acids (74). The amino acids generally found

in nature are of the L-form (75). Two compounds,

diaminopimelic acid (DAP)and muramic acid are also found

only in cell walls. The structures of DAP and muramic

acid are shown in Figure 4. Work (76) first identified DAP,

while the structure of muramic acid was elucidated by

Strange (77) and Strange and Kent (78).

Since the discovery that the cell walls of Gram­

positive organisms contained a relatively small number of

components (71, 79), much more time has been spent trying

to elucidate the structure of these cell walls than the

cell walls of Gram-negative organisms. The Gram-negative

organisms of the genus Spirilla, however, have been an aid

since it was found that their glycosaminopeptide layers

could be isolated in a pure form by treating the cell walls

with aqueous solutions of sodium dodecylsulfate (25).

Studies on the molecular structure of cell wall

glycosaminopeptide have advanced rapidly in the last few

years. Information has been gained from several sources,

Page 33: The amino acid and monosaccharide content of the cell

Table 1. Principal Classes of Chemicals Found in

Cell Walls of Bacteria {29, p. 251).

Gram-positive

Gram-negative

Glycosarninopeptides Oligosaccharides Polysacchardies Teichoic Acids Teichuronic Acids Glycolipids

Glycosarninopeptides Proteins Lipids Polysaccharides Lipo-Polysaccharides Lipo-Proteins

23

Page 34: The amino acid and monosaccharide content of the cell

COOH COOH

I I H N-C-H H-C-NH

2 I I 2 CH-2-cH2

a-E Diaminopimelic Acid (DAP)

NH 2

Muramic Acid

Figure 4. Structures of a-E Diaminopimelic Acid and Muramic Acid (76, 77, 78).

24

Page 35: The amino acid and monosaccharide content of the cell

including the elucidation of the "Park nucleotides'' which

accumulate within the cell when some organisms are grown

in the presence of penicillin and other antibiotics. The

investigation of products from acid and lysozyme degraded

cell walls has also aided in the determination of the

glycosaminopeptide structure. Salton (80) made a major

discovery when he found a disaccharide in the dialyzable

fraction of a lysozyme degraded cell wall preparation. He

also found a similar compound in an acid hydrolyzate (81).

The nature of this and another dialyzable tetrasaccharide

component was reported by Ghuysen and Salton {82, 83).

25

The diasaccharide was found to be acetylglucosamine joined

by a 1-6 linkage to N-acetylmuramic acid. The tetrasac­

charide was composed of two moles each of acetylglucosamine

and N-acetylmurarnic acid.

The postulated structures of these compounds are shown

in Figure 5. These data led Salton and Ghuysen (83) to

propose a structure for glycosaminopeptide with a backbone

of acetylglucosarnine and N-acetylmuramic acid with alter­

nating 1-4 and 1-6 bonds. This proposed structure ~s shown

in Figure 6. In addition to these, some dialyzable

glycosaminopeptides of low molecular weight were also

found. These were separated by paper chromatography and

found to contain alanine, glutamic acid, lysine, glycine,

glucosamine and muramic acid. The amino acids were postu­

lated to be in the peptide side chain (Figure 6) •

Page 36: The amino acid and monosaccharide content of the cell

~CH2 0

H

H NHCOCH 3 0

I CH 3CHCOOH

0

H ~--' H H

NHCOCH 3 \ H NHCOCH 3

CH 3CHCOOH

H

H

(a)

CH 3CHCOOH \ 0

(b)

26

Figure 5. The Proposed Structure of Amino Sugar, Di-and-Tetra­saccharides from Micrococcus _lysodeikticus (82) .

(a) Amino sugar disaccharide isolated from lysozyme digestion mixture.

(b) Amino sugar tetrasaccharide isolated from lysozyme digestion mixture.

Page 37: The amino acid and monosaccharide content of the cell

(1-+6)

~Backbone Structure~

(1-+4) (1-+6) (1-+4) (1-+6) (1-+4) (1-+6)

-AG-AMA AG AMA AG :AMA--AG AMA--

Peptide Peptide

Figure 6. Type of Molecular Structure Proposed for the Cell Wall of Micrococcus lysodeikticus (83).

This figure shows the arrangement of side chains on an acetyl amino sugar backbone possessing alternating 1-+4 and 1-+6 bonds between N-acetyl-muramic acid (AMA) and N-acetyl-glucosamine (AG).

I'V -...]

Page 38: The amino acid and monosaccharide content of the cell

28

Park (84) in 1952 found that a number of nucleotides

accumulated in the cells of organisms grown in the presence

of penicillin. The structure of the "Park nucleotides",

when elucidated, gave an indication of the structure of

the peptide chain proposed by Salton and Ghuysen (83)

(Figure 6). A structure of one of the "Park nucleotides"

which is thought to be a precurser to glycosaminopeptide

is given in Figure 7. These data can be used to infer the

structure of the peptide chain, as well as its linkage to

the disaccharide shown in Figure 6.

Ghuysen (85) isolated two glycosaminopeptides from the

lysozyme-digested cell walls of Micrococcus lysodeikticus.

Each of the compounds had the same molar proportions of

components. For each mole of glutamic acid found in the

glycosaminopeptide there were found 2 moles of disaccharide,

2 moles of alanine, 1 mole of glycine and 2 moles of lysine.

These two glycosaminopeptides were separated by electro­

phoresis. Treatment of the glycosaminopeptides with an

enzyme, Streptomyces F2B amidase, liberated a disaccharide

similar to the one first described by Salton and Ghuysen

(83) (Figure 6) and a peptide. The new N-terminal group

of the peptide was alanine. Therefore, alanine was bonded

directly to the muramic acid through an amide bond just as

in the "Park nucleotide" (Figure 7). Salton (86) has also

shown that alanine is the amino acid linked to the muramic

acid found in the cell walls of several organisms.

Page 39: The amino acid and monosaccharide content of the cell

lr~~ o- o-H-c-c-c-c- I I I I CH20-P-O-P = 0

H H ~ b I

Uridine - 5' Diphosphate

0

NH p I HC - CH C=O I 3 I I

C = 0 CH3 : 1-- ---------------- ~ NH I

I : HI - CH3 I

C = 0 I ,_ -- ________________ ., NH I

I I

TH- (cH2> 2 c = o :

~~QH __ - -----1----- ----~ I NH

Muramic Acid

L - Alanine

D-Glutamic Acid

I HC -I

L-Lysine {CH 2 ) 3-c,H2

I C = :--------!H 0 NH2

D-Alaninei H!- (CH3 I c = 0

.. -------I I NH

: I D-Alanine: HC - CH 3

I I L -- - - - - COOH

Figure 7. Structure of a "Park Nucleotide" from Staphylococcus aureus (25} .

29

Page 40: The amino acid and monosaccharide content of the cell

Primosigh et al. {87) found two low molecular weight

glycosaminopeptides in digests of the rigid portion of

Escherichia coli cell walls. Pelzer (88) analyzed the

structures of these compounds. The structures are shown

in Figure 8. The amino acid make up differs from that

found in Figure 7, in that lysine has been replaced by

diaminopimelic acid.

30

On the basis of the compounds isolated and studied bY

Ghuysen (85) and on hydrazinolysis experiments, Salton (86)

proposed a model for the cell walls of Micrococcus lyso-~

deikticus. This model is shown in Figure 9.

According to Salton (29, p. 146-147), Schacher, Bayley,

and Watson have suggested the hypothetical glycosaminopep­

tide unit shown in Figure 10 as being the basic cell wall

unit of Aerobacter cloacae.

Staphylococcus aureus from which the 11 Park nucleotide"

shown in Figure 7 was isolated, has a cell wall composed of

two polymers, glycosaminopeptide and teichoic acid. The

structures of four basic types of teichoic acid are shown

in Figure 11. The cell walls of Staphylococcus ~

contain Type b teichoic acid. Mandelstam and Strominger

(89) have carried out further investigations on the

teichoic acid and glycosaminopeptide fractions of

Staphylococcus aureus and have suggested a possible mode

of teichoic acid glycosaminopeptide attachment. This mode

Of attachment is shown in Figure 12. Since glycine was not

found in the "Park nucleotides 11 these investigators proposed

Page 41: The amino acid and monosaccharide content of the cell

31

GnAc GnAc - lactyl GnAc GnAc - lactyl

I I L -ala L -ala

I I D -glu D -glu

I {COOH)

I meso DAP meso -DAP

I Compound c5 D -Ala (COOH)

Compound c6

Figure 8. Structure of Two Glycosaminopeptides Isolated from Escherichia coli Cell Walls (88).

The glycosaminopeptides were isolated from the rigid layer of lysozyme digested cell walls of Escherichia coli B.

Page 42: The amino acid and monosaccharide content of the cell

R - GnAc - GnAc --- Rl

I lactyl

I ala I

ala I

glu

I lys (- e:NH 2 ) I

gly I

( e:NH-) - gly (- COOH) lys I

glu I

ala I

ala I

lactyl

I 111 R - GnAc - GnAc -

32

Figure 9. Hypothetical Glycosaminopeptide Subunit of the Cell Wall of Micrococcus lysodeikticus (86).

Page 43: The amino acid and monosaccharide content of the cell

Ala

Glu

DAP

Ala

H NH I

O=C I CH 3

H

0 H

~TH C=O

r------------1 I NH I I I CH-CH3 I I I C=O 1------------1 I NH

H

0

33

NH 2 COOH---, I I I

HOOC-CH-(CH) -CH IDAP 2 3 I I

NH : 1-------4 C=O I I I

HOOC-(CH 2) 2-CH :Glu I I NH I

1------..f C=O I I I

CH 3-CH 1Ala I :

NH I 1----- __ J

C=O I

CH3"CH if 0

II NH-C-CH 3

I I I yH-(CH2)2-COOH

I C=O ~-----------1 I NH NH2 : I I

TH-(CH2)3-CH-COOH

I C=O 1-----------1

NH I CH-CH 3

I I ""-- - - - - - -- COOH

Figure 10. Hypothetical Subunit of the Cell Wall of Aerobacter cloacae (29, 147).

Page 44: The amino acid and monosaccharide content of the cell

34

(a) ~lanyl - glucosyl - ri~ito~ L O=P-OH I n

(b) ~lanyl - N - acetylglucosaminyl - ribttoll

L O=P-OHJ I n

(c) [

lanyl - glycefolJ

O=P-OH I n

(d) ~anyl - glycosyl - gly,ero~ L O=r-OHJ 0

Figure 11. Four General Types of Teichoic Acid (29, p. 159).

Page 45: The amino acid and monosaccharide content of the cell

- GnAc - GnAc - GnAc - GnAc -

I I lactyl lactyl

I I L-ala L-ala

I I ~ /D-glu '\ ~,..........D-gllu , rl\.i'\ ~

~ '? I l~\.i -J ~,~ ~"i. L-lys,.......... L-lys

/'--~ I D-ala

I D-ala

D-ala I

D-ala I

GnAc GnAc GnAc I

GnAc I I

-Ribitol - P - Ribitol - P - Ri~itol (a)

- P - Ribitol - P -

- GnAc - GnAc - GnAc - GnAc -I I

lactyl lactyl I I

L-ala L-ala / I :i" '? I ).1" 1-

..........-o-glu '\.~-...;. 'o-glu '\.~

=1"< I / I/ '\.~-...;. L-lys L-lys / I I

D-ala D-ala I I

D-ala D-ala

I I GnAc GnAc GnAc

"" I ~ GnAc

R.l. - ~u~tol - P - Ribitol - P - Ribitol - P -

(b)

Figure 12. Proposed Structure of Cell Walls of Staphylococcus aureus (89).

35

In representation a, the linkage between and glycosaminopeptide is not specified. b the teichoic acid is shown attached to tide.

the teichoic acid In representation

the glycosaminopep-

Page 46: The amino acid and monosaccharide content of the cell

36

that glycine served as a peptide bridge between the peptide

side chains of the glycosaminopeptide.

There are still many questions concerning glycosamino­

peptides and cell walls which have not been answered. For

example, the mode of teichoic acid attachment, the mode of

oligo-and polysaccharide attachment, the precise sequence

of the amino acids in the peptide side chains, and the sig­

nificance of the undialyzable fraction of lysozyme digested

cell walls are not known. However, some common structural

properties have been established in all the studies of

glycosaminopeptides. They possess a glycosidically-linked

backbone composed of alternating units of N-acetylglucosa­

mine and N-acetylmuramic acid and the peptides are linked

through the amino group of alanine and the carboxyl group

of muramic acid. It is now known that the chemical com­

ponent responsible for the rigidity of cell walls in both

the Gram-positive and Gram-negative species is glycosamino-

peptide (29, p. 8, and 81).

Some data relating the qualitative and quantitative

aspects of the amino acid analyses of bacterial cell walls

are given in Tables 7, 8, and 9, p. 79, 82, 84 of subsequent

sections.

To analyze the components of the cell wall, the cell

wall itself must be isolated. The isolation of the cell

wall generally follows the sequence: (a) separation of

the cells, (b) pretreatment of the cells, (c) disruption of

the cells, (d) separation of the cells, cell walls and cell

components, and (e) purification of the cell walls.

Page 47: The amino acid and monosaccharide content of the cell

37

The general procedure for collection and concentration

of the cells is centrifugation of the cell suspension. The

pretreatment consists of washing with salt or buffer solu­

tion, or distilled water. If the cells are pathogenic they

can be killed before washing. Some organisms which clump

may be pretreated with surfactants to reduce aggregation.

The cells may be disrupted by several methods (29,

p. 42-63) : {a) autolysis, {b) osmotic lysis, {c) heat

treatment rupture, and {d) mechanical disintegration.

Autolysis is a process in which the organism is placed

in a solvent and allowed to lyse. The disadvantage of this

process is that some bacteria contain lysozyme-like enzymes

which actively destroy their cell walls. If the solvent

used does not immediately kill the organism, the isolated

cell walls may be depleted of certain chemicals due to the

utilization of the cell wall by the starved organism. There

is, therefore, some doubt that the cell wall material iso­

lated in this manner is completely intact.

Osmotic lysis is a process in which the organism is

grown in a medium of high solute concentration. The medium

is then rapidly diluted and this causes the cell wall to

rupture. This method works very well with halophilic

organisms.

Heat treatment rupture is a process in which the

organisms are added to hot water for a short period,

thereby causing the organism to rupture. This procedure

Page 48: The amino acid and monosaccharide content of the cell

has not been found applicable to Gram-positive organisms

(29' p. 42-63).

38

Mechanical disintegration consists of a group of

processes in which the cell walls are physically and

mechanically ripped apart. Mechanical disintegration is

the most versatile method of disruption. There are several

methods of mechanical disintegration: (a) grinding, violent

aggitation or compression with abrasives such as sand, glass

beads, steel balls or alumina; (b) sonic or ultrasonic dis­

integration; (c) decompression rupture; and (d) pressure

cell disintegration.

After the cells are ruptured, the cell components, the

cell walls, and the unruptured cells must be separated.

The separation can be made by differential centrifugation

or by density gradient sedimentation (90).

Differential centrifugation is centrifugation at dif­

ferent speeds in order to separate particles of different

size. The unruptured cells are separated by centrifugation

at relatively low speed. The supernatant of this separa­

tion is decanted into another centrifuge tube and the cell

walls and cell components are separated by centrifuging at

a higher speed. A scheme for this type of separation is

given in Figure 13.

Density gradient sedimentation is a separation carried

out by placing the cells, cell walls, and other cell com­

ponents in a layer over a solution which has been carefully

placed in a centrifuge tube. The solution in the centrifuge

Page 49: The amino acid and monosaccharide content of the cell

39

DISINTEGRATE CELL SUSPENSION

Deposit {Intact cells}

Discard

Centrifuge

2,000 - 3,000 xg; 5-10 minutes

Supernatant (cell walls, cytoplasm)

Centrifuge

5,000 - 9,000 xg

20 minutes

Deposit {crude cell wall fraction)

Supernatant (cytoplasmic

material)

Figure 13.

Discard

General Scheme for Differential Centrifugation (29, p. 58).

Page 50: The amino acid and monosaccharide content of the cell

40

tube is then added in a manner such that it has a density

gradient. Sucrose and glycerin are the solutes generally

used to produce the gradient. After the layer of cellular

material is placed on top, the tube is centrifuged for

several minutes. This causes the cells, cell walls, and

cell contents to separate into three separate layers which

can then be removed.

The cell walls may be purified by several methods.

The first and probably the best method is repeated washing

with distilled water. Salton (29, p. 42-63) recommended

the use of sodium chloride solutions, while others have

used various buffers. Cummings and Harris (79) have used

a procedure in which they digested the cell walls with

trypsin and ribonuclease followed by digestion with pepsin.

This procedure may or may not remove antigens and other

surface components from the cell wall.

Page 51: The amino acid and monosaccharide content of the cell

41

III. EXPERIMENTAL

A. MATERIALS AND METHODS

Cultivation of Cells. The strain of Thiobacillus

thiooxidans used for this study was culture number 8085,

American Type Culture Collection (ATCC), 2122 M Street, N.W.,

Washington, D. C.

After the culture obtained from ATCC was growing well,

several 5 ml samples were taken. These samples were

maintained in a cold room (4 C) in a liquid state, and were

used to start a new stock culture periodically. The stock

culture in use at the time was routinely transferred to a

fresh medium once every seven days. In either case a flask

containing 100 ml of medium was inoculated with 5 ml of

inoculum from the stock culture.

The medium employed in this work was as follows:

(NH4 ) 2so4 0.2 g

MgS04 ·7H20 0.5 g

CaC1 2 0.25 g

KH2Po4 3. 0 g

FeS04 trace (0.01) g

Sulfur 10.0 g

H20 1000 ml

To prepare the medium, the salts were dissolved in the

water. The medium without sulfur was sterilized for 30

minutes in an autoclave (Rectangular type 24x36x48 inches,

Page 52: The amino acid and monosaccharide content of the cell

42

American Sterilizer Co., Erie, Pa.) at a temperature of

120 C and pressure of 15 PSIG. The sulfur was added with­

out sterilization, just before the medium was inoculated

with organisms. This was done because sulfur was found to

form an amorphous mass on sterilization, thus reducing the

exposed surface available for oxidation by the organism.

The pH of the medium was in the range of 4.0 to 4.8.

The cells were grown in a 16 liter fermentor described

by Crum (91). An over-all sketch of the apparatus used is

given in Figure 14. All cell growth took place at ambient

temperature conditions which ranged from 21 to 28 C. The

cells were grown in the medium described previously. Growth

was started by inoculating the previously sterilized fer-

mentor with 270 ml of stock culture. The stock culture

had been allowed to grow for seven days on a rotary shaker

{Model CS-62630, New Brunswick Scientific Co., New

Brunswick, N. J.). The incubation was stopped after eight

days. Experiments were run to determine if surfactants

would aid in the growth of the organism. These are

described in a following section of this chapter.

The growth of T. thiooxidans was followed by titration

of the sulfuric acid formed by the organism. Titrations

were performed in the following manner. An appropriate

volume of medium {usually 10 ml) was taken, filtered, and

the residue washed with four volumes of deionized water.

The combined filtrate and washings were then diluted to

Page 53: The amino acid and monosaccharide content of the cell

Thermometer Well1 ....

Motor

..<"rio

Sample Port Ferrnentor

'"""

0 0 0 0 0 0 0 0

0 0 0

I I I

/-/---+-' Agitator z Air

Sparger

Air Filter

pH Electrodes

l

pH Meter

Pressure --------t Regula tor

t I I Rotameter

Figure 14. Sketch of Fermentation Apparatus (91).

Air Supply

~

w

Page 54: The amino acid and monosaccharide content of the cell

44

approximately 150 ml and titrated with 0.1 N sodium hy­

droxide using phenolphtalein as the indicator.

The cells grown in the fermentor were harvested by

continuous centrifugation (Model LCA-1, High Speed Centri­

fuge, Lourdes Instrument Corp., Brooklyn, N.Y.) at 4,250

to 4,500 x g .

Cells which were not to be used immediately were

stored in the frozen state.

Preparation of Cell Walls. Two pretreatment pro-

cedures were employed before the cells were ruptured. The

first pretreatment, which was used in all cases, consisted

of washing the cells three times with deionized water. If

the cells were stored in the frozen state for any length

of time, they were again washed three times with deionized

water before they were used. The second pretreatment,

which was evaluated experimentally but not used in routine

work, was that described by Suzuki and Werkman (57). This

pretreatment consisted of treating the cells in solution

with two ion exchange resins. The procedure was as follows:

To the cell suspension of 10 to 20 mg of washed cells per

ml (dry weight) in deionized water was added 2 g of AG-1X2

(Bio-Rad., 32nd and Griffin Streets, Richmond, Calif.) and

2 g of IR-120 (Bio-Rad.) ion exchange resins. The cell

suspension and ion exchange resins were thoroughly mixed

and placed on the rotary shaker for 20 minutes. The

mixture was filtered to remove the ion exchange resins,

and the cells ruptured in the usual manner.

Page 55: The amino acid and monosaccharide content of the cell

45

The cells were ruptured by two methods; extrusion under

high pressure through a small aperature and sonication.

The procedure for the extrusion rupturing was as fol­

lows: The pretreated cells were suspended in enough buffer

or deionized water to give a suspension of 10 to 20 mg of

cells per ml (dry weight) . The cell suspension was placed

in the precooled (4 C) compression chamber (Catalogue

No. 4-3398 American Instrument Co., Inc., Silver Springs, Md.).

The compression chamber was placed on a press (Model No. 12-

105 Wabash Metal Products Co., Wabash, Ind.), and the cells

were forced out at a pressure of 16,000 to 20,000 PSIA by

regulation of the control valve on the compression chamber.

The cell suspension was collected in a small beaker sur­

rounded with ice. In most cases the cells were returned to

the compression chamber and expressed as above a total of

three times. However, some samples were tested after going

through the process only once.

The procedure for sonication was as follows: The pre-

treated cells were placed in a 100 ml Rosett cooling cell or

a 50 ml polycarbonate centrifuge tube. Enough buffer or

deionized water was added to give a suspension with 10 to

20 mg of cells per ml (dry weight). The cell suspension,

in its receptacle, was lowered into an ice water bath. The

suspension was sonified (Model 575, Sonifier, Branson Sonic

Power, Division of Branson Instruments Inc., Danbury, Conn.)

for the specific time interval required at a power input of

6.6 to 7.1 amperes. When samples were taken for protein

Page 56: The amino acid and monosaccharide content of the cell

determination, they were taken from the supernatant after

the entire cell suspension had been centrifuged at 13,000

~ g for 10 minutes. Enough buffer or deionized water was

then added to the system to bring it back to its original

volume to keep the volume constant.

The whole cells, cell walls, and cell components were

separated after cell rupture as follows: ~he whole cells

were removed by centrifuging at 2,100 x g for 10 minutes.

The supernatant was then centrifuged for 20 minutes at

8,400 x g. The sedimented cell walls were saved for

further purification by linear sucrose density centrifuga-

tion.

46

Linear sucrose density centrifugation was used to

further purify the crude cell walls obtained by differen­

tial centrifugation of the ruptured cells. The apparatus

used is shown schematically in Figure 15. After the rubber

tubing was clamped, 25 ml of sucrose (40gper 60 ml of

1 M potassium chloride solution) and 25 ml of 1 M potassium

chloride solution were added to chamber A and B respec­

tively. All bubbles were forced out of the rubber tubing

and the air was turned on. After the clamp was opened,

about 5 ml of the solution in chamber A was drawn into a

small beaker through a 2.5 mm (outside diameter) plastic

tUbe. The beaker was replaced with a 50 ml polycarbonate

centrifuge tube and about 35 to 40 ml of solution was

carefully drawn from chamber A in a manner which allowed

Page 57: The amino acid and monosaccharide content of the cell

47

Air B

T 9"

Plastic Tube

Clamp

Figure 15. Device used to Produce Linear Sucrose Gradients.

Page 58: The amino acid and monosaccharide content of the cell

48

stratification. The clamp between chambers A and B was

closed and the solution remaining in chamber A was used to

suspend the cell walls to be treated. This was accomplished

by sonication at about 2 amperes for 30 seconds. The sus-

pended cell walls were carefully layered on the surface of

the sucrose gradient. The centrifuge tube was then care­

fully placed in an International horizontal rotor centri-

fuge (Model CL No. 50204 H International Equipment Co.,

Boston, Mass.}, and centrifuged at 1,500 to 1,600 x g for

60 to 90 minutes. Generally only two layers were observed,

however, sometimes three layers were found when doing the

initial linear sucrose gradient. The separate layers

formed are described in Figure 16. The cell wall layer was

removed with a 50 ml syringe with a size 15 cannula. The

same procedure was repeated a second time.

The cell walls after two linear sucrose centrifuga­

tions were washed three times with deionized water, three

times with 1 M sodium chloride, and then three more times

with deionized water.

Cell walls were tested for contamination by intra-

cellular material by measuring their absorption of light

in the ultraviolet range. The spectrophotometer used was

a Beckman DK-2A Automatic Scanning Spectrophotometer

(Beckman Instruments, Inc., 2500 Habor Blvd., Fullerton,

Calif.).

Cell not to be used immediately were walls which were

stored in the frozen state (-15 C)·

Page 59: The amino acid and monosaccharide content of the cell

(a)

Figure 16. Layers Formed During Linear Sucrose Gradient Purification-

(a) Precipitate of intact cells. (b) Yellow Phase. (c) Cell wall layer.

49

Page 60: The amino acid and monosaccharide content of the cell

Cell Wall Components. The components of the cell

wall were identified by hydrolysis followed by paper

chromatography or amino acid analysis. Some cell walls

were digested with trypsin preceding hydrolysis.

For the determination of the amino acid content of

50

the cell walls, the walls were hydrolyzed in 6N hydro­

chloric acid for various periods of between 12 and 24 hours.

The cell walls at a concentration of 100 mg per ml (wet

weight) and the hydrochloric acid were sealed in a pyrex

tube for digestion. The sealed glass tubes were inserted

into a 3/4 x 8 inch pipe with nipples on both ends, and

the pipe was placed in a convection hot air oven (Model 16,

Precision Scientific Co., Chicago, Ill.) at 103 to 107 C.

After the selected time had elapsed, the tube was removed

from the oven, cooled and opened. The residue in the tube

was filtered through filter paper and washed with deionized

water. The filtrate and washings were evaporated to

dryness on a Rinco (Model 1007-4 Rinco Instrument Co.,

Greenville, Ill.) evaporator. The residue was dissolved in

deionized water and the mixture evaporated to dryness. This

procedure was repeated two more times.

Cell walls for sugar and polyol analysis were hydro-

lyzed by two different methods. The first method was

hydrolysis for two hours in 2N sulfuric acid at 100 to

103 C. This digestion was also carried out in a sealed

PYrex tube as described above except that an oil bath

Page 61: The amino acid and monosaccharide content of the cell

51

maintained at a temperature of 100 to 103 c was used rather

than the hot air oven. The digested material was adjusted

to pH 4.5 with solid barium hydroxide. The barium sulfate

and other insoluble material formed was removed by centri­

fugation. The supernatant was taken nearly to dryness on

the Rinco evaporator.

The second method was digestion in the presence of

IR-120 ion exchange resin. About 1 g of wet resin and

about 0.1 g of wet cell walls along with 3.5 ml of water

were added to a pyrex tube. The test tube was sealed, and

the contents digested for 24 hours at 120 C in the hot a1r

oven. The residue was filtered and the filtrate taken to

dryness on the Rinco evaporator.

The cell walls to be digested with trypsin were placed

in a pH 7.9 buffer solution containing 0.5 mg per ml of

trypsin. Approximately 20 mg of wet cell walls were added

per ml of buffer solution. The cell walls and buffer were

thoroughly mixed in an erlemeyer flask. The flask was

placed in a shaking, constant temperature bath (Model RW

150 C, New Brunswick Scientific co., New Brunswick, N.J.),

and the cell walls digested for two hours at 35 C. The

residue was separated by centrifugation and washed once

With buffer and three times with deionized water. The

wash solutions were discarded and the residue, which con­

tained the treated cell walls, was digested with 6 N hydro­

chloric acid in a sealed pyrex tube as described previously.

Page 62: The amino acid and monosaccharide content of the cell

52

Paper chromatograms for amino acid detection were

prepared by the two-dimensional ascending method. The paper

used was 11 by 11 inch Whatman No. 1 filter paper. The

first solvent used was butanol, acetic acid, and water

(120:30:50:vol./vol.}. The second solvent was phenol,

water, and concentrated ammonia (182:18:l:vol.jvol.). The

amino acids were located by spraying with ninhydrin in

acetone. The ninhydrin spray was prepared by mixing 2 g of

ninhydrin with 100 ml of acetone.

The amino acids were identified by comparing their Rf

values with those from papergrams prepared with solutions

of known compounds, and by adding known samples along with

the unknown and determining if the spots overlapped. The

Rf values were defined as: the length the sample moved

divided by the length the solvent front moved. If known

solutions were not available, Rf values were compared

with those given by Smith (97).

The sugars and polyols were separated by single dimen-

sional descending paper chromatography. The paper used was

11 by 22 inch Whatman No. 1 filter paper. The solvent used

was butanol, acetic acid, and water. The proportions were

the same as given previously. The sugars were located by

spraying with either periodate or silver nitrate spray

reagents. Silver nitrate spray was prepared by adding 0 · 1

ml of saturated silver nitrate solution to 100 ml of

acetone. After spraying the papergram with silver nitrate

spray reagent, it was dried and then sprayed with a O.S%

Page 63: The amino acid and monosaccharide content of the cell

53

solution of sodium hydroxide in ethanol. Sugars gave brown

or black spots with this treatment.

Both sugars and polyols can be located with periodate

spray. The periodate spray was prepared by mixing 1 ml of

periodic acid (2.28 g in 100 ml of deionized water) and

19 ml of acetone. The periodic acid-acetone mixture was

sprayed on the dry papergram and it was allowed to stand

for 3 to 4 minutes. The paper was then sprayed with a

benzidine solution prepared by mixing 184 mg of benzidine

in 0.6 ml of acetic acid, 4.4 ml of water, and 95 ml of

acetone. Sugars and polyols gave a white spot on a blue

background.

Sugars and polyols were identified by comparing their

Rg values to those of known samples run in a similar manner.

The R values were defined as: the length the sample moved g

divided by the length the glucose sample moved.

The quantitative amino acid analyses of digested cell

walls were performed by the Experiment Station Chemical

Laboratories of the college of Agriculture at the University

of Missouri, Columbia, Missouri.

The samples were prepared by digestion, filtration, and

washing as already described. The filtrate and washings

were collected in a previously weighed glass ampule. The

digestion mixture was taken to dryness and water was added.

This operation was repeated four times. The dry samples

were then stored in a dessicator overnight. After drying

Page 64: The amino acid and monosaccharide content of the cell

54

in the dessicator the ampule was again weighed. The ampules

were sealed after weighing and stored in the frozen state.

The following procedure was used by the Experiment

Station Chemical Laboratory. The samples were dissolved in

10 ml of 0.1 M hydrochloric acid, and 4 ml samples were

chromatographed on a Technicon Amino Acid Analyzer.

Protein and Nitrogen Determinations. Protein and

nitrogen determinations were used to measure the amount of

cell rupture produced during rupture experiments.

Protein was determined by precipitation with trichlo­

roacetic acid (TCA) , and the precipitated protein measured

by the biuret method (93) as follows: The sample was added

to a 15 ml graduated centrifuge tube. A volume of 50% TCA

equal to approximately one quarter the sample volume was

added, and the mixture was brought to at least 3 ml with

10% TCA. The suspension was mixed and allowed to stand

for 5 to 15 minutes. The supernatant was drawn off leaving

0.2 to 0.3 ml. With the aid of a spatula the precipitate

was thoroughly mixed with the remaining liquid. Eight ml

of biuret reagent was added and the solution and precipi­

tate mixed until the precipitate was completely dissolved.

The solution was brought to 10 ml and allowed to stand for

30 minutes. After this period the optical density of the

samples were measured at 540 m~ in a Bausch and Lomb

Spectronic 20 Colorimeter (Bausch and Lomb, Incorporated,

Rochester, N. Y.). A blank was prepared in a similar

m A standard curve was prepared anner using deionized water.

Page 65: The amino acid and monosaccharide content of the cell

55

using a solution of bovine serum albumin (BSA). To prepare

the biuret reagent the following procedure was used: 1.50 g

of hydrated cupric sulfate (Cuso 4 .sH20) and 6.0 g of sodium

potassium tartrate (NaKC 4H40 6) were weighed and transferred

to a dry one liter volumetric flask. The salts were dis­

solved in 500 ml of previously boiled deionized water.

Three hundred ml of 10% sodium hydroxide, prepared from a

30% stock solution diluted with boiled deionized water, was

added with constant swirling. The solution was then

brought to one liter with boiled deionized water. The

biuret reagent was stored in a polyethylene bottle under

refrigeration (4 C).

The second means of protein determination was a spec-

trophotometric method outlined by Seaman (94) . The sample

was diluted until an optical density reading could be taken

at 260 m~ with a Hitachi-Perkin Elmer, Model 139, Spectro­

photometer (Coleman Instruments corporation, Maywood, Ill.)·

The optical density was then measured at 280m~. The ratio

of the optical density at 280 m~ to the optical density at

260 m~ was used to determine a factor, F, given by Seaman.

The amount of protein was calculated as follows: mg pro­

tein/ml = F x optical density at 280 m~ x dilution.

The soluble nitrogen in the supernatant of samples

centrifuged at 13,000 x g for 10 minutes was used as a

m 1 t Nitrogen was deter-easure of the degree of eel rup ure.

mined by the Kjeldahl method and the procedure employed was

as follows: To each clean dry 100 ml Kjeldahl flask was

Page 66: The amino acid and monosaccharide content of the cell

56

added 1.5 g of potassium sulfate. Then enough liquid

sample was added to supply from 0.6 to 6.0 mg of nitrogen.

To each flask 1.5 ml of mercuric sulfate solution (prepared

by diluting 12 ml of concentrated sulfuric acid to 100 ml

and adding 10 g of red mercuric oxide) was added. Three or

four glass beads and 3 ml of concentrated sulfuric acid

were added to each flask. The flasks were heated on a

Kjeldahl digestion rack (Laboratory Construction Co.,

Kansas City, Mo.) until the water had been boiled off and

white sulfur trioxide fumes were no longer formed. The

solution at this point was completely clear. The clear

solution was then boiled for 30 minutes and allowed to cool.

Twenty-five ml of distilled water was added to each flask,

and the flasks were again cooled. Fifteen ml of 13 N sodium

hydroxide was then carefully added to the Kjeldahl flask

in an ice bath. The sodium hydroxide formed a layer on the

bottom of the flask. After the sodium hydroxide was added

the flask was connected to the Kjeldahl distillation ap­

paratus with as little mixing as possible. At this point a

boric acid trap was placed on the condenser of the distilla­

tion apparatus. The boric acid trap was prepared by adding

20 ml of 2% boric acid and two drops of Tashiro's indicator

to a 125 ml erlenmeyer flask. The Tashiro's indicator was

prepared by adding 0.25 g of methylene blue and 0.375 g of

methyl red to 300 ml of 95% ethanol. The tip of the

condenser was placed as far as possible below the surface

Page 67: The amino acid and monosaccharide content of the cell

of the boric acid. The digested mixture and the sodium

hydroxide were then mixed and the solution was boiled for

20 to 25 minutes. At this point salt had started to form

in the digestion flask. The boric acid bath was removed

and the condenser tip washed down with 3 ml of distilled

water before the flask was taken off the distillation

57

apparatus. The ammonia trapped in the boric acid solution

was titrated with 0.02 N sulfuric acid. The Tashiro's

indicator turned from green to grey at the end point. Each

ml of 0.020 N sulfuric acid was equivalent to 0.28 mg of

nitrogen.

Surfactant Studies. Tergitol 08 and TWeen 80

surfactants were tested to see if they would enhance the

growth of T. thiooxidans. TWeen 80 was supplied by Atlas

Chemical Industries, Inc., Chemicals Division, Wilmington,

Del. and Tergitol 08 by Union carbide Corporation, South

Charleston, W. Va.

Initial tests for foaming were obtained by passing

air through a fine capillary tube into the culture medium

containing sulfur in a 500 ml erlenmeyer flask. The amount

The medium of foam resulting was visually observed.

containing surfactant was also tested by placing it on the

rotary shaker and shaking for various periods, and then

tested for foaming in the described manner.

tests Were made using TWeen 80 as a Two fermentation

wetting agent. These tests were made in the same manner as

those described under "Cultivation of Cells" (p. 41 > with

Page 68: The amino acid and monosaccharide content of the cell

58

the exception that Tween 80 was added after the medium had

been sterilized and before the sulfur was added. The tests

were performed in a two liter capacity fermentor described

by Li (92) which allowed visual observation.

I t I ·~

'

Page 69: The amino acid and monosaccharide content of the cell

59

B. RESULTS

Surfactant Studies. Two surfactants, Tergitol 08 and

Tween 80, were examined to see if they would reduce the lag

period found in the growth of the organism Thiobacillus

thiooxidans.

From visual observation it was found that Tergitol 08

1n concentrations of 50 to 500 ppm partially wet the sulfur

in the medium and caused it to be more evenly distributed

when the medium was incubated on the rotary shaker for a

period of seven days. However, some sulfur remained on the

surface, when the medium was aerated for a short period.

The sulfur rose to the surface and floated on a layer of

foam. This problem did not occur with Tween 80. The

foaming effects of TWeen 80, as visually evaluated, seemed

minimal.

Experiments were performed to determine the effect of

Tween 80 concentration on growth. The growth of the

organism was followed by measuring the formation of acid.

The study was performed in 500 ml erlenmeyer flasks incubated

on the rotary shaker. The data from this study are given

in Table 2 and plotted in Figures 17 and 18. Figure 18

gives the data for the samples containing 12.5 ppm TWeen 80

and for the sample containing no TWeen 80 expanded near the

origin. f tor constructed by

Two tests were made in a glass ermen

Ll. (g 2). 'th TWeen 80 concentrations These tests were made W1

Of 1 lt e g iven in Table 3 and 2.5 and 50 ppm. The resu s ar

Page 70: The amino acid and monosaccharide content of the cell

Table 2.

Incubation 0 -Time (Hours)

0 3.9

24 6.0

60 13.9

84 20.2

108 26.9

168 41.0

288 57.0

432 65.1

The Effect of Surfactant Tween 80 on the Growth

of Thiobacillus thiooxidans. Shake Flask Studies. -

Tween 80 Added (ppm)

12.5 50 100 -Sulfuric Acid Formed (MEQ./100 ml}

3.8 3.7 3.4

6.4 5.9 5.5

14.8 14.2 11.9

21.1 19.5 17.4

26.6 25.5 24.0

40.6 39.0 35.6

55.6 54.7 54.6

64.1 62.5 62.9

230

3.4

4.0

5.4

8.6

10.3

23.6

43.6

51.2

0'1 0

Page 71: The amino acid and monosaccharide content of the cell

70

60

~

...:I ::E: 0 50 0 r-4 ......... . 0

~ 40 0 IJ:l

I I I ~ 0 no wetting agent 0 ~'>.!

30 i I I i Ill 0 no wetting agent 0

0 12.5 ppm Tween 80 H u

20 j I I e 230 ppm Tween 80 l ~ 0 50 ppm Tween 80 ~

u H 1 f7/ e 100 ppm Tween 80 ~ :::J ~'>.! ..:I :::J tl)

10

0 0 4 8 12 16

TIME OF INCUBATION (DAYS)

0 20 4 8 12 16 TIME OF INCUBATION (DAYS)

20

F'iqurc 17. The F.ffect of Surfactant Tween 80 on the l.irowth of Thiohacillus thiooxidans. Shake Flask Studies. 0'1 1-"

Page 72: The amino acid and monosaccharide content of the cell

30

~ ~

0 0 r-1 '-. ()I li:l ~ -0 ri:j

~ 0 r:t..

0 H t) ~

t) H p:; :::::> r:t.. ....::1 :::::> 5 U)

0 0

Figure 18.

62

0 no wetting agent added

• 12 ·5 ppm Tween 80

60 80 100 20 40

120

TIME OF INCUBATION (HOURS)

The Effect of Surfactant TWeen 80 on the Growth of Thiobaci11us thiooxidans. Shake Flask Studies.

Page 73: The amino acid and monosaccharide content of the cell

Table 3. The Effect of Surfactant Tween 80 on the Growth of

Thiobaci11us thiooxidans. Fermentor Studies.

No Tween 80 Added 12.5 EEm Tween 80 Added 50 ppm Tween 80 Added Incubation H~SO' Formed Incubation H~SO' Formed Incubation H2so' Formed Time (Hours) { EQ 100 m1) Time (Hours) ( EQ 100 m1) Time (Hours) (MEQ 100 m1)

0 2.6 0 2.6 0 1.8

24 2.7 12 3.0 8 1.7

38 3.0 24 3.6 23 2.0

49 3.5 34 4.0 35 2.1

61 5.6 46 7.3 47 2.6

82 11.6 58 9.5 60 2.6

98 21.8 70 11.1 80 2.7

109 28.0 80 12.2

122 30. 3 94 12.8

144 36.2 106 13.2

168 38.7 118 13.9

191 41.8 141 14.7

"" 217 45.9 185 16.2 w

Page 74: The amino acid and monosaccharide content of the cell

and Figure 19. For comparison, the data from a test using

no surfactant are also included in Figure 19.

Cell Rupture. Two methods were employed to rupture

64

the cells. They were sonication and pressure cell rupture.

Sonication was performed by exposing the suspended cells to

ultrasonic waves which ruptured the cell walls. For

pressure cell rupture the suspended cells were compressed to

a high pressure and forced through a small orifice. In

addition to washing with deionized water, some cells were

pretreated by contacting them with ion exchange resins. The

rupture of cells was studied in deionized water and in a

basic buffer (pH 7.9) solution. The results of these

experiments are summarized in Table 4.

The per cent soluble nitrogen given in Table 4 was

defined as the ratio of the Kjeldahl nitrogen in the super­

natant centrifuged at 13,000 x g for 10 minutes to the total

Kjeldahl nitrogen in the sample before treatment.

The paper chromatograms for the Paper Chromatography.

detection of amino acids were prepared by the two dimensional

ascending method. The amino acids were located by spraying

with ninhydrin. The solvents used were butanol, acetic

acid, and water (120:30:50:vol./vol.) and phenol, water, and The amino acids

concentrated ammonia (182:18:l:vol./vol.) •

Were identified by comparing Rf values with those from

papergrams prepared with known solutions and by adding

known samples along with the unknowns and determining if

the spots overlapped. The Rf values for those amino acids

Page 75: The amino acid and monosaccharide content of the cell

-..:I ::E: ..........

• 01 ~ ~ -0 ~

~ 0 ~

0 H 0 F:l! u H ~ ::::::> ~ H :::> til

50

I I

40

30

20

' 10

0

0

no Tween 80 added ~

I - 12.5 ppm ~ween 80 added

50 ppm Tween 80 added

40 80 120 160 200 240

INCUBATION TIME (HOURS)

Figure 19. The Effect of Surfactant Tween 80 on the Growth of Thiobaci11us thiooxidans. Fermentor Studies.

0'1 l11

Page 76: The amino acid and monosaccharide content of the cell

Table 4. Thiobacillus thiooxidans Cell Rupture Experiments.

Test I Test II Test III

Type of Rupture: Pressure Cell Sonication Pressure Cell

Pretreatment: (a) (a) (b)

Solvent: Deionized Water Deionized Water Deionized Water

Soluble Nitroqen Release Data

(c) Number of Soluble Time Soluble Number of Soluble

Times Nitrogen of Nitrogen Times Nitrogen Through Release Sonication Release Through Release P. Cell (%) (Minutes) (%) P. Cell (%)

1 18.8 0 6.2 1 9.2

3 24.6 1 9.6 3 11.3

3 11.9

4 13.3

5 13.7

8 14.8 0'1 0'1

Page 77: The amino acid and monosaccharide content of the cell

Table 4 (Continued). Thiobacillus thiooxidans Cell Rupture Experiments.

Type of Rupture:

Pretreatment:

Solvent:

Time of

Sonication (Minutes}

0

10

20

30

TEST IV Sonication

(b)

Deionized Water

TEST V Pressure Cell

(a)

pH 7.9 Buffer (d)

Soluble Nitrogen Release Data

Soluble Number of Nitrogen Times

Release Through (%} P. Cell

0.5 1

5.5 3

8.8

9.0

(a) Cells were washed three times with deionized water.

Soluble Nitrogen

Release (%)

--48.5

67.9

(b} Cells were treated with 2g of AG-1X2 and 2g of IR-120 ion-exchange resin. (c) The per cent soluble nitrogen is defined as: nitrogen in supernatant centrifuged

at 13,000xg for 10 minutes divided by total nitrogen in suspension before treatment. (d) Buffer prepared by mixing: 936 ml of M/15 Na 2Po4 and 64 ml of M/15 KH 2Po 4 .

0'\ ......

Page 78: The amino acid and monosaccharide content of the cell

68

which were not available as standard solutions were taken

from data given by Smith (97). Table 5 gives the amino

acids found in hydrochloric acid digests of cell walls using

paper chromatography.

The sugars were separated by single dimensional descend­

ing paper chromatography. They were identified by spraying

with silver nitrate spray reagent. The solvent used was

butanol, acetic acid, and water in the same proportions as

given in the preceeding paragraph. The sugars were identi­

fied by comparing R values with those of known sugar g

samples. The sugars identified by paper chromatography in

the IR-120 ion exchange digestion mixture were: rhamnose,

glucose, and galactose. Traces of the amino sugar

glucosamine were found on the amino acid papergrams.

Amino Acid Analysis. The results of amino acid

analyses of cell walls prepared by hydrochloric acid

hydrolysis and trypsin digestion followed by hydrochloric

ac · d h bl 6 These analyses are ~ ydrolysis are given in Ta e •

given on a gram per lOOg of cell wall basis, and on a gram

per 100 g of dry hydrolyzate basis. Column three of Table 6

g . J.'n amJ.'no acids after digestion ~ves the per cent reduction

With

for

the

trypsin. The cell walls were tested

!est for Contamination. · of light in . the absorptJ.on

contamination by measurJ.ng d b Salton (95) and

ultraviolet region as suggeste Y typical curve for the

Keeler et al. t from a pressure

cell Walls and a sample of the supernatan

( 96) • Figure 20 gives a --

Cell rupture.

Page 79: The amino acid and monosaccharide content of the cell

69

Table 5. The Qualitative Amino Acid Content of

Thiobacillus thiooxidans Cell Walls.

Amino Acid

Alanine

Arginine

Aspartic acid

Cysteic acid

Cystine

Diaminopimelic acid

Glutamic acid

Glycine

Histidine

Leucine/Isoleucine

Lysine

Methionine

Methionine sulphoxide

Phenylalanine

Proline

Serine

Threonine

Tyrosine

Valine

(a) + + large, intenselY colored + =

+ + = fairly large spot;

+ = small but definite spot;

- no spot found.

Relative Amounts {a)

+ + +

+

+ +

+

+

+ + +

+ +

+ +

+ +

+ +

+ +

+

+ +

+ +

+ +

+ +

spot on chromatogram;

Page 80: The amino acid and monosaccharide content of the cell

Table 6. The Quantitative Amino Acid Content of Thiobacillus thiooxidans Cell Walls.

Cell Wall Basis Dry Hydrolyzate Basis Trypsin Tryps1n

Digestion Digestion Followed Loss of Followed Loss of

HCl by HCl Amino HCl by HCl ;..mino Digestion Digestion Acid Digestion Digestion Acid

Amino Acid (g/lOOg} (g/lOOg} ( % } (g/lOOg) (g/lOOg) ( %)

Alanine 2.20 0. 361 84.5 3.64 1.552 57.5 Arginine 1.77 0.020 98.9 2.94 0.086 97.0 Aspartic

Acid 2.72 0.395 85.4 4.52 1.696 62.4 Diamino-pimelic acid (a) (a) -- (a) (a) Glutamic acid 3.30 0.468 85.9 5.49 2.01 63.5 Glycine 1.45 0.221 84.9 2.41 0.948 60.6 Half-Cystine 0.05 TRACE -- 0.09 TRACE Histidine 0.58 0.054 91.5 0.97 0.230 75.3 Isoleucine 0.98 0.094 90.7 1.62 0.403 75.4 Leucine 2.40 0.321 86.6 3.99 1.380 65.4 Lysine 1.11 0.107 90.0 1.84 0.460 75.0 Methionine 0.53 TRACE 100.0 0.88 TRACE 100.0 Ornithine 0.16 0.087 43.7 0.26 0.374 -44.0 Phenylalanine 1.16 0.167 85.4 1.93 0.719 62.7 Proline 1.16 0.120 89.7 1. 9 3 0.517 73.1 Serine 1.37 0.301 78.0 2.28 1.292 43.5 Threonine 1.11 0.187 82.9 1.84 0.805 56.0 Tyrosine 1.00 0.147 85.0 1.67 0.632 62.3 Valine 1.59 0.254 84.3 2.63 1.092 58.6

24.64 3.304 86.6 40.93 1.320 67.9

(a) Its presence is suspected but was not quantitatively established. -....]

0

Page 81: The amino acid and monosaccharide content of the cell

-dP -z 0 H 8 ~ ~ 0 tl.l

~

~ H 8 < ...:I IJ;:I ~

100

90

80

70

60

50

40

30

20

10

0 230

supernatant

cell walls

240 250 260 270 280 290 300 310 320 WAVE LENGTH (mf.l)

Figure 20. Ultraviolet Absorption of Cell Walls and Supernatant from Pressure Cell Rupture.

330

-J ........

Page 82: The amino acid and monosaccharide content of the cell

72

IV. DISCUSSION

A. DISCUSSION OF RESULTS

Surfactant Studies. Investigations by Schaeffer (65)

and Jones and Benson (66) indicated that Thiobacillus

thiooxidans produced a large amount of surface active agent.

Schaeffer identified this agent as phosphatidyl inositol,

while Jones and Benson have reported that the agent is

phosphatidyl glycerol. The surface active agent presumably

aids in wetting the sulfur and thus aids in the oxidation of

the sulfur.

Earlier work by Starkey, Jones, and Frederick (62) with

surfactants indicated that of eight surfactants studied only

Tergitol 08 and Tween 80 accelerated the oxidation of sulfur

in shake flask studies.

The surfactants Tergitol 08 and TWeen 80 were studied

in this work for their ability to reduce the lag phase of

growth during the culture of T. thiooxidans. It was reasoned

that a reduction of the lag phase would decrease the time

required to produce a given amount of cells.

The 08 Was abandoned after visual obser-use of Tergitol

vations of its effect on the sulfur suspended in the medium.

Aeration of the shaken media containing Tergitol 08 for

h f in the media to rise 5 ort periods of time caused the sul ur

to the surface. The sulfur was retained there by a layer of

f · 1 08 tested were 50 to oam. The concentrations of Terg~to

sao ppm. It was assumed that if the sulfur floated on the

Page 83: The amino acid and monosaccharide content of the cell

73

surface of the fermentation vessel ' then the organism would

not have ample access to the sulfur and the rate of sulfur

oxidation would be reduced. Foam also created operating

problems in the fermentor.

Visual observations of media containing Tween 80 indi­

cated that this surfactant did not have the undesirable

properties of Tergitol 08. Tween 80 allowed immediate

dispersal of sulfur in shake flasks and foaming seemed to

be minimal.

Shake flask studies of growth using Tween 80 as a

Wetting agent were undertaken. The total amount of acid

produced by the organism was reduced by the presence of

Tween 80 in the medium. Tween 80 at a concentration of

12.5 ppm did, however, increase the initial rate of oxida-

tion (Figure 18, p. 62) This initial increase in rate was

probably the result of the ease with which the organisms

could attach themselves to the sulfur particles when a sur-

factant had been added to the medium. However, Tween 80

must have also inhibited the growth of T. thiooxidans and

consequently the oxidation of sulfur to some extent.

Pilot scale fermentations were carried out using 12.5

and 50 ppm concentrations of Tween 80. These tests (just

as did the shake flask studies) indicated that a concentra­

tion of 12.5 ppm Tween 80 increased the initial rate of

growth. very little growth occurred at a concentration of

50 ppm Tween 80 (Figure 19, p. 65). In shake flasks growth

still occurred at 230 ppm Tween 80 (Figure 17, P· 61). The

Page 84: The amino acid and monosaccharide content of the cell

growth in the fermentor was limited because the violent

aeration and agitation caused the medium to foam. The

sulfur was retained on the surface of this foam where it

was not accessible to the organism.

It was concluded that the use of Tween 80 or Ter­

gitol 08 was not effective in increasing the yield of

T. thiooxidans cells in pilot scale fermentors.

74

Cell Rupture. Experiments were conducted to determine

the most efficient manner for rupturing the cells. The

amount of protein released from washed cells was evaluated as

an index of the degree of cell rupture. Initially attempts

were made to measure the protein released using the biuret

method (93) and the spectrophotometric method (94). Neither

of these methods was found applicable for the solutions

involved. The biuret method seemed to give consistent data,

although not all of the material precipitated with trich­

loroacetic acid could be completely dissolved in some cases.

The amount of protein determined by the biuret method dif­

fered greatly from that determined by the spectrophotometric

method. Because of the difficulties encountered with the

determination of protein, soluble nitrogen was also evaluated

as a means for determining the degree of cell rupture.

Nitrogen was determined by the Kjeldahl procedure. This was

found to be a reliable method and, consequently, it was used

for all the cell rupture studies.

suzuki and Werkman (57) found T. thiooxidans resistant

to rupture by sonication unless the cells were pretreated

Page 85: The amino acid and monosaccharide content of the cell

75

with a mixture of anionic and cationic ion exchange resins.

They treated the cells with IR-120 and IR-4B ion exchange

resins in distilled water. A similar pretreatment using

AG-1X2 ion exchange resin to replace IR-4B was tried. This

pretreatment was not found to be a satisfactory method for

increasing the degree of cell rupture. In fact, it reduced

the amount of soluble nitrogen in the final suspension of

broken cells, when compared to that of untreated cells. Part

of this decrease might have been due to the fact that the

ion exchange resins removed some of the nitrogen initially

present in the samples. As shown in Table 4, Test II, p. 66

the initial amount of soluble nitrogen present in an

untreated sample was 6.2%, while in a pretreated sample

(Test IV) only 0.5% was present. The soluble nitrogen

initially present could have come from the rupture of cells

while in the frozen state, or as a result of insufficient

washing of the cells prior to treatment. The ion exchange

resins might have also affected the permeability of the cell

wall allowing some nitrogenous material to escape without

actual rupture of the cells.

Since a very small release of the total nitrogen took

place in deionized water, (Table 4, p. 66) a basic buffer

(pH 7.9) was tested as a medium for cell rupture. Because

T. thiooxidans can withstand acid conditions but cannot

live under basic conditions it was felt that the basic

buffer might aid in cell rupture. This basic buffer (pH 7.9)

was adopted for routine work, with no further study at other

Page 86: The amino acid and monosaccharide content of the cell

hydrogen ion concentrations, because it gave a five or six

fold increase in soluble nitrogen release as compared to

deionized water (Table 4, p. 66).

The pressure cell rupture method was adopted for

routine work because it gave more soluble nitrogen than

sonication. Comparison of Test I with Test II, Table 4,

p. 66, indicates that putting the cells through the pres­

sure chamber once gave more rupture than eight minutes of

sonication. Tests III and IV of Table 4 show that about

30 minutes of sonication gave about the same amount of

soluble nitrogen as did the running the cells through the

pressure cell once.

76

Hydrolysis Methods. Cell walls hydrolyzed for 2 hours

at 100-103 c with 2 N sulfuric acid gave no indication of

sugars or polyols when the solutions were chromatographed.

The reason sulfuric acid did not give sugar residues is

probably linked to the high resistance of the organisms to

sulfuric acid.

Keeler et al. (96) were able to solubilize the indi-

vidual monosaccharides in the cell walls of Vitrio fetus

by adding the ion exchange resin Permutit Q to the cell

walls and heating the suspension for 24 hours at 120 C in

a sealed tube. A similar digestion procedure using the ion

exchange resin IR-120 gave solutions in which rhamnose,

glucose, and galactose could be detected by paper chroma-

tography.

Page 87: The amino acid and monosaccharide content of the cell

77

Rhamnose was easily detected by the chromatographic

method employed. A special procedure was used to separate

glucose and galactose since they have essentially the same

Rg values in the chromatographic solvent employed. The

glucose in the sample was destroyed using glucose oxidase.

The cell wall hydrolyzate, glucose, galactose, and a mix-

ture of glucose and galactose were incubated with glucose

oxidase at room temperature for six hours. The solutions

were filtered and evaporated under vacuum in a Rinco

evaporator until two or three drops remained. All the

samples containing glucose, including the cell wall hydro­

lyzate, gave a spot on a chromatogram corresponding to

gluconic acid, the expected product from the action of

glucose oxidase on glucose. A galactose spot was observed

on the chromatograms containing this monosaccharide.

A The Sugars found in the cell nalysis of Cell Walls.

Walls hydrolyzed with IR-120 ion exchange resin were

rh Sugars found in other amrose, glucose, and galactose.

cell 1 271) arabinose, fucose, wa ls are (95, 29, p. : 'b and tyvelose.

galactose, glucose, mannose, rhamnose, r~ ose, on the amino acid

Traces of glucosamine were also detected

Papergrams of the cell wall hydrolyzates of T. thiooxidans.

· was not The . 'd or galactosam~ne presence of muram~c ac~

detected. Salton (29, P· 114) has mentioned that all been found in bacter­

three of the above amino sugars have

f g lucosamine present The small amount 0 ial cell walls.

Page 88: The amino acid and monosaccharide content of the cell

78

in the cell wall points to the similarity of the cell walls

of T. thiooxidans and cell walls of Gram-negative bacteria

Figure 2, p. 20).

The analysis of cell walls hydrolyzed with hydro-

chloric acid differed somewhat depending on the method of

analysis. The results of the analysis using the Amino

Acid Analyzer (Table 6, p. 70) indicated that three com­

pounds not found by paper chromatography (Table 5, p. 69)

were present in the cell wall hydrolyzates. They were

ornithine, phenylalanine, and tyrosine. The Amino Acid

Analyzer did not detect the presence of diaminopimelic

acid, glucosamine, cysteic acid, and methionine sulphoxide.

The reason phenyalanine was not detected by paper chroma­

tography was that its Rf value is very similar to that of

leucine and isoleucine and the spots may have overlapped

on the chromatograms. Likewise, tyrosine has an Rf value

very near that of valine and methionine. The reason

diaminopimelic acid did not show up in the Amino Acid

Analyzer was probably due to the proximity of its peak to

that of methionine and isoleucine in the amino acid analy­

sis. Likewise, glucosamine and valine would probably form

only one peak. The small amounts of cysteic acid and

methionine found by paper chromatography might be due to

the variations of the composition of the cell walls.

A comparison of the more qualitative data from paper

chromatography, (Table s, p. 69) with data given by Salton

(95), Table 7, indicated that it is very difficult to

Page 89: The amino acid and monosaccharide content of the cell

Amino Acid

Alanine Arginine Aspartic acid Cysteic acid Cystine Diaminopimelic

acid Glutamic acid Glycine Histidine Leucine Isoleucine Lysine Methionine Methionine sulphoxide Phenylalanine Proline Serine Threonine Tyrosine Valine

Table 7. The Qualitative Amino Acid Content of Some Gram-

positive and Gram-negative Bacterial Cell Walls (95).

Streptococcus pyogenes

+ + + (a) +

+ + +

+ + + + +

+ + + + +

+ + +

+ + + +

+ +

Gram-positive Organisms

Streptococcus faecalis

+ + +

+

+ + +

+ + + +

+ +

+

Micrococcus lysode1ktus

+ + +

+ + + +

+

---

Sarcina lutea

+ + +

+

+ + + + +

+ +

--

-

Bacillus subtillus

+ + +

+

+ + + + + +

+

+ +

+ +

+

-...)

~

Page 90: The amino acid and monosaccharide content of the cell

Table 7 (Continued). The Qualitative Amino Acid Content of Some Gram-positive

and Gram-negative Bacterial Cell Walls (95).

Gram-negative Organisms

Amino Acid Escherichia

Alanine Arginine Aspartic acid Cysteic acid Cystine Diaminopimelic acid Glutamic acid Glycine Histidine Leucine/Isoleucine Lysine Methionine Methionine sulphoxide Phenylalanine Proline Serine Threonine Tyrosine Valine

(a)+ + + = large, intensely colored + + = fairly large spot

+ = small but definite spot no spot found

col1

+ + + (a) +

+ + + -+

+ + + + + -

+ + + + +

+ + + +

+ + + +

+ + +

spot on chromatogram

Salmonella pullorum

+ + + +

+ +

+ + + +

+ + +

+ + +

+ + + +

+ +

00 0

Page 91: The amino acid and monosaccharide content of the cell

81

distinguish between Gram-positive and Gram-negative bacteria

on the basis of the amino acids present in the hydrolysis

of cell walls. One obvious disadvantage of this system is

that each person may assign the "+++", "++", "+", and "-"

different relative values. Comparison of the quantitative

amino acid data shown in Table 6, p. 70, with the data

reported by Salton (29, p. 254-255) and shown in Table 8,

shows however, that T. thiooxidans cell walls more closely

resemble those of Gram-negative than those of Gram-positive

organisms. It should be noted that for Lactobacillus casei

(a Gram-positive bacterium} the three major amino acids

make up 65% of the amino acids present, and the five major

components make up 80% of the amino acids present. In

Streptococcus faecalis (another Gram-positive organism)'

the three major amino acids make up 90% of the amino acids

present. For T. thiooxidans and the Gram-negative bacteria

no single amino acid makes up more than about lO to lS% of

the total amino acids present.

Of Of amino acids per Summation of the number grams

1 Gram-negative cell 00 g of cell wall indicates that the

f inc acids Walls are composed of a greater percentage 0 am

Therefore, the than Gram-positive cell walls (Table 8>·

d . T thiooxidans more closely amount of amino acids faun J.n ~ ~~~~---

't' bacteria. resembles that found in Gram-posJ. J.Ve

acJ.'ds found on hydrolysis is The amount of amino

· The data dependent upon the conditions of hydrolys~s.

Page 92: The amino acid and monosaccharide content of the cell

Table B. The Quantitative Amino Acid Content of Some Gram-positive

and Gram-negative Bacterial Cell Walls (29, p. 254-255).

Gram Positive Organisms Gram Negative Organisms

Amino Acid

Alanine Arginine Aspartic acid Diaminopime1ic

acid Glutamic acid Glycine Half-Cystine Histidine Isoleucine Leucine Lysine Methonine Ornithine Phenylalanine Proline Serine Threonine Tyrosine Valine Total

Lactobacillus casei

g/lOOg {a)

8.4 - (b)

3.1

6.7 7.2 1.0

1.4 1.4 2.3

0.6 1.1

1.4 34.6

Streptococcus faecalis

g/lOOg

12.0

0.8

5.4 0.2

0.4 0.4 4.5

0.2 0.2

0.24 24.3

Escherichia coli

g/lOOg

5.6 3.8 7.1

+ (b) 6.9 3.1

0.9 3.7 5.3 4.0 0.7

3.0 1.5 3.7 3.8 3.3 3.4

59.8

(a) All values are given on a cell wall basis. (b) ~-" indicates that the concentration was not estimated;

"+" indicates that the amino acid was present.

Pseudomonas aeruginosa

g/lOOg

5.1 1.3 9.3

3.2 5.8 7.1

2.8

1.7

7.3

5.4

4.2 3.9

57.1

Salonella bethesda

g/lOOg

4.3 0.4

14.5

2.1 4.9 5.5

1.6

0.5

4.1

2.6

2.5 2.0

45.0

(X)

N

Page 93: The amino acid and monosaccharide content of the cell

given in Table 8 are for the hydrolysis of the cell walls

in 6 N hydrochloric acid at a temperature of 100 to 105 c '

83

for periods from 12 to 24 hours. Although this is the most

general method of hydrolysis, Salton (29, p. 105) has

pointed out that the release of amino acids may be maximal

for a shorter digestion period. Salton also pointed out

that the maximum amount of diaminopimelic acid and lysine

was formed after only about 8 hours of hydrolysis in 4 or

6 N hydrochloric acid at 105 C. It is possible that if

different conditions of digestion were employed for the

hydrolysis of T. thiooxidans cell walls the amount of amino

acid per 100 g of cell wall might have been brought into

better agreement with those of Gram-negative organisms. If

cell walls from various microorganisms were digested under

similar conditions but for varying periods of time, such as

2 hour intervals over the range of 2 to 24 hours, one could

then determine the optimum digestion period. This diges­

tion period would probably be different for each organism

examined.

Comparison of the molar ratios of amino acids present

in cell walls, Table 9, also indicates that the cell wall of

T. thiooxidans is more like that of Gram-negative than Gram­

positive bacteria. The molar ratios of glycine and serine

are more like those of the Gram-negative than the Gram­

positive organisms. The molar ratios of amino acids in

~ thiooxidans are more like those of the Gram-negative

Page 94: The amino acid and monosaccharide content of the cell

Table 9. Molar Ratios of Some Amino Acids in Cell Walls.

Organism Lysine Glutamic Acid Glycine Serine Alanine

Escherichia coli 1.0 1.7 1.5 1.3 2.2

Pseudomonas aerug~nosa 1.0 3.4 8.3 4.4 4.9

Salmonella bethesda 1.0 9.7 21.0 7.2 14.1

Thiobacillus th~oox~dans 1.0 2.9 2.6 1.7 3.3 -Lactobacillus casei 1.0 3.1 0.9 0.4 6.0

StreEtococcus ·faecalis 1.0 1.2 0.1 0.1 4.4

(a} Data taken from Tables 6 and 8, p. 70 and 82.

(a)

Gram-Reaction

+

+

+

ro ~

Page 95: The amino acid and monosaccharide content of the cell

85

bacterium Escherichia coli than any of the other bacteria

listed in Table 9.

The amino acid analysis of the trypsin digested cell

walls indicated that 87% of the cell wall amino acids were

removed. The per cent reduction in amino acids was calcu-

lated as follows:

grams of amino acid per 100 g of cell wall in the hydrochloric acid digest

grams of amino acid per 100 g of cell wall in the trypsin digest

grams of amino acid per 100 g of cell wall in the hydro­chloric acid digest

X 100

using data obtained from Table 6, p. 70. If it is assumed

that trypsin digestion removed all the amino acids except

those in the glycosaminopeptide, and that the percentage of

amino acids in the cell wall and the glycosaminopeptide were

constant, then 13% of the cell wall could be considered to

be glycosaminopeptide. This is well within 10 to 20 % range

cited by Salton (29, p. 99-100) for glycosaminopeptide in

Gram-negative cell walls. It is unusual to find ornithine as a component of cell

1 . has not been found in

wa ls. To the author's knowledge 1t found may have been an

any other cell walls. The ornithine

artifact formed during the cell rupture procedure. orni-

thine ;s product of arginine formed under ~ a degradation

basic conditions. peptide bonds where The enzyme trypsin is specific for

. ·ne or L-lysine. the d by L-arg1n1

carboxyl group is donate

Page 96: The amino acid and monosaccharide content of the cell

The enzymes will not hydrolyze peptides composed entirely

of ornithine (98).

Trypsin digestion removed 99% of the arginine, 100%

of the methionine, and only 44% of the ornithine present

~n the cell walls of T. thiooxidans. From these data the

sequence of the peptide in which arginine and ornithine

were located cannot be ascertained, but most of the

arginine residues must have been located near lysine ~n

order to be completely removed. Ornithine, on the other

hand, must have been located in peptides which contained

fewer lysine and arginine bonds. If ornithine were formed

from arginine during the rupture procedure, it would most

likely have been formed at the surface of the cell wall.

The trypsin digestion data, however, would indicate that

arginine in the surface layer was a portion of a peptide

with a very small amount of lysine, and this could account

for the small loss of ornithine formed from the arginine.

Another possibility is that the glycosaminopeptide which

86

is resistant to trypsin digestion, contained a high propor-

tion of ornithine.

In order to determine if ornithine is initially

present in the cell walls enough cells must be ruptured in

deionized water to make amino acid analysis possible. If

ornithine is not found in this analysis this would indicate

that the ornithine was formed during the cell rupture at

pH 7.9.

Page 97: The amino acid and monosaccharide content of the cell

87

From the above results it may be concluded that the

cell walls of T. thiooxidans more closely resemble the cell

walls of Gram-negative than the Gram-positive bacteria and

that there is a possibility that the cell walls of

T. thiooxidans contain ornithine.

Test for Contamination. Cell walls were tested for

contamination by intracellular material (nucleic acid) by

measuring their absorption of light in the ultraviolet

range. This procedure measured the contamination by intra­

cellular material, and was suggested by Salton (29, p. 42-63)

and Keeler et al. (96). The results, shown in Figure 20,

indicate that the cell walls did not absorb at 260 m~ as did

the supernatant from the cell rupture. This indicates that

the cell walls were not contaminated with intracellular

material. Salton (29, p. 96) has stated that the high light

scattering of the cell walls might mask the absorption at

260 m~ resulting from the presence of nucleic acid.

Page 98: The amino acid and monosaccharide content of the cell

88

B. LIMITATIONS

Salton (29, p. 42-63} reported that the most useful

guide for the determination of cell wall homogeneity was the

electron microscopic examination. With the aid of electron

microscopy one could determine if the cell walls were con-

taminated with flagella. The flagella are very easily

removed from bacteria (96). Keeler et al. (96) used dif­

ferential centrifugation at 68,000 x g for 1 hour to harvest

flagella of Vibrio fetus from other cell fragments. The

cell walls of Thiobacillus thiooxidans in the present study

were harvested at 8,400 x g for 20 minutes. Therefore,

the flagella were probably lost during the differential

centrifugation. Two criteria of homogeneity were also

mentioned by Salton (29, p. 42-63}: spectroscopic examina­

tion of cell walls for intracellular chemical components,

and the separation of cell walls in sucrose density gradients.

At the time this experiment was conducted, an electron

microscope was not available on this campus. For this

reason electron micrographs could not be used as an indica­

tion of homogeneity. The cell walls were, however, collected

using the sucrose densitY gradient method. The examination

of the ultraviolet absorption of the cell walls gave no

evidence of the presence of intracellular components.

Therefore, the author felt justified in assuming that the

cell walls were homogeneous in nature.

Page 99: The amino acid and monosaccharide content of the cell

89

The ATCC strain number 8085 of !:._ thiooxidans was used

in this experiment. Other strains of !.:_ thiooxidans cell

walls might exhibit differences in cell wall composition.

Page 100: The amino acid and monosaccharide content of the cell

V. CONCLUSIONS

From the results obtained in this investigation the

following conclusions were made:

90

(1) The use of the surfactants Tergitol 08 and Tween 80 was

not effective in increasing the cell yield of

Thiobacillus thiooxidans in pilot scale fermentors.

(2) The best rupture of T. thiooxidans cells was obtained

using a basic buffer (pH 7.9) and the pressure cell

rupture technique.

(3) The hydrolysis of cell walls for sugar residue was best

performed using digestion with the ion exchange resin

IR-120 and not sulfuric acid.

(4) The cell wall of T. thiooxidans was found to have an

amino acid content more like that of Gram-negative than

Gram-positive organisms.

(5) The possibility that ornithine was present in the cell

walls of T. thiooxidans was indicated.

(6) The cell wall of T. thiooxidans was found to contain the

sugars, rhamnose, glucose, and galactose. It also con­

tained small amounts of the amino sugar glucosamine.

Page 101: The amino acid and monosaccharide content of the cell

91

VI. RECOMMENDATIONS

The following method is suggested for large scale

growth of the organism Thiobacillus thiooxidans. It depends

on a semi-batch type fermentation. The fermentor should be

charged with medium and inoculated with organisms. After

the organisms have reached maximum growth, 80 to 90% of the

medium should be withdrawn and replaced with fresh medium.

The cycle should then be repeated.

Recommendations for further study include:

(1) Electron microscopic examination of cell walls for

homogeneity and surface appendages.

(2) Rupture of enough cells in deonized water to determine

if ornithine is present in walls not ruptured under basic

conditions.

(3) Study to determine if trypsin is specific for ornithine

residues found in peptides.

(4) Study to determine if trypsin will liberate amino acids

from glycosaminopeptides.

(5) Further study of cell wall hydrolysis methods.

(6) Examination of the cell walls for the presence of lipids.

(7) Quantitative study of the cell wall monosaccharide

composition.

Page 102: The amino acid and monosaccharide content of the cell

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

92

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I I I I I I I I I I I

I I I I I I I I I I I I I I I

I I I I

~ I

I I I I I

I I I

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LePage, G.A. and Umb.:reit w w 11 h hydrate Esters . ' .• , .P osphorylated Carbo-

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Newburgh, R. W., "Phosphorylation and Chemosynthesis by Thiobaci11us thiooxidans," J. Bact., 68, 93-97 (1954). --

Suzuki, Isamu and Werkman, C.H., "Chemoautotrophic Fixation of Carbon Dioxide by Thiobacillus thio­oxidans," Iowa State Coll. J. Sc1.. , 32, 4 75-4 8 3 ( 1953) • --

Suzuki, Isamu and Werkman, C.H., "Chemoautotrophic Carbon Dioxide Fixation by Thiobaci11us thiooxi­dans . I. Formation of Oxalacetic Acid, " Arch. B~ochem. Biophys., 76, 103-111 (1958).

suzuki Isamu and Werkman, C.H., "Chemoautotropic C~rbon Dioxide Fixation by Thiobacillus thiooxidans II. Formation of PhosphoglycerJ.c AcJ.d,n Arch. Biochem. Biophys., 77, 112-123 (1958).

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61. Knaysi, Georges, "A Cytological and Microchemical Study of Thiobacillus thiooxidans," J. Bact. 46 451-461 (1943}. ' _,

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63. Jones, G.E. and Starkey, R.L., "Surface Active Sub­stances Produced by Thiobacillus thiooxidans," J. Bact., ~, 788-789 (1961).

64. Vogler, K.G. and Umbreit, W.W., "The Necessity for Direct Contact in Sulfur Oxidation by Thiobacillus thiooxidans," Soil Sci., 51, 331-337 (1941).

65. Schaeffer, W.I., "Biochemical Studies with the Sulfur Oxidizing Bacterium Thiobacillus thiooxidans," Ph.D. Thesis (1964) p. 1-30, Rutgers Un1versity, New Brunswick, New Jersey. ·

66. Jones, G.E. and Benson, A.A., "Phosphatidylglycerol in Thiobacillus thiooxidans," J. Bact., 89, 260-261 (1965}. --

67. Vogler, K.G., LePage, G. A. and Urnbreit, W.W., "Studies on the Metabolism of Autotrophic Bacteria I. The Respiration of Thiobacillus thiooxidans on Sulfur," J. Gen. Physiol., 26, 89-102 (1942).

68. Fischer, D.J., Herner, A.E., Landes, Alma, Batlin, Alex, and Barger, J.W., "Electrochemical Observations in Microbiological Processes. Growth of Thiobacillus thiooxidans. I," Biotech. Bioengr., 7, 471-490 {1965). -

69. Fischer, D.J., Landes, Alma, Sanford, M.T., Herner, A.E. and Wiegand, C.J.W., "Electrochemical Observations in Microbiological Processes. Growth of Thiobacillus thiooxidans. II," Biotech. Bioengr., 71 491-506 (1965).

70. Salton, M.R.J. and Horne, R.W., "Studies of the Bacterial Cell Wall II. Methods of Preparation and Some Properties of Cell Walls," Biochirn. et Biophys. Acta, 7, 177-197 (1951).

71. Salton M.R.J., "The Nature of the Cell Walls of Some G;am-Positive and Gram-Negative Bacteria," Biochim. et Biophys. Acta, ~, 334-335 (1952).

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Baddiley, J., Buchanan, J.G. and Carss B. "The Presen~e ?f R~bitol Phosphate in Bact~rial Cell Walls, Blochlm. et Biophys. Acta, 27, :220 (1958).

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Salton, M.R.J., "The Anatomy of the Bacterial Surface, 11

Bacterial. Revs., 25, 77-99 (1961}.

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Ghuysen, J.M. and Salton, M.R.J., "Acetylh~xosarnine Compounds Enzymically Released fro~ Mlcrococcus . lysodeikticus Cell Walls I. Isolatlon and ~omposl­tion of Acetylhexosamine and Acetylhexosamlnepep­tide Complexes," Biochim. et Biophys. Acta, 40, 462-472 (1960).

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83. Salton, M.R.J. and Ghuysen, J.M., "Structure of Di- and Tetrasaccharides Released from Cell Walls by Lysozyme and Streptomyces F. Enzyrne and the B (1~4)-N-~ce~ylh~xosaminidase Activity of these Enzymes, B1och1m. et Biophys Acta 36 552-554 (1959}. • , _,

84. Park, J.T., "Uridine-5'-pyrophosphate derivatives. I. Isolation from Staphylococcus aureus, II. A Structure Common to Three Derivatives III. Amino Acid Containing Derivatives " J. Biol: Chern, 194, 877-904 (1952). , -

85. Ghuysen, J .M., "Structure of the Disacch.aridepeptide Complexes Freed by B(l~4) N-acetylhexosarninidases from Micrococcus lysodeikticus Cell Walls," Bioch1m. et B1ophys. Acta, 47, 561-568 (1961).

86. Salton, M.R.J., "Bacterial Cell Wall. VIII. Reaction of Walls with Hydrazine and Fluorodini trobenzene 1"

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101

VIII. ACKNOWLEDGEMENT

The author wishes to express his appreciation for the

patient guidance and counsel afforded by his advisor, Dr. D.

J. Siehr, throughout the course of this investigation.

Special thanks is expressed to the author's second

reader, Dr. s. G. Grigoropoulos, and to his typists, Miss

Janet Davidson and Mrs. K. W. Davidson, who spent many hours

rushing this text to completion.

Page 112: The amino acid and monosaccharide content of the cell

102

IX. VITA

Edward H. Crum was born on September 21, 1940, at

South Charleston, v-lest Virginia where he obtained his

primary educRtion. He received his secondary education at

Saint Albans, West Virginia, graduating from high school in

June 1958.

In September of this same year he entered West Virginia

Institute of Technology where he received a B.S. degree in

Chemical Engineering in June 1962.

He was awarded a National Defense Act Fellowship in the

spring of 1962. This fellowship was awarded in the field of

Engineering Biochemistry.

He entered the. graduate school of The University of

Missouri School of Mines and Metallurgy in September 1962

where he received a M.S. in Chemical Engineering in Hay, 1964.

The title of his thesis was "The Submerged Culture of

Thiobacillus thiooxidans in a Pilot Scale Permenter."

He is a member of the American Institute of Chemical

E · Amer~can Chern~cal Society, and the Instrt~ent ng l.neers, ..... ......

Society of America.

He was married to Kathryn Ann Duckworth on November 29,

1963. They have one child William H. who was born October

28, 1964.