ch 3 powerpoint biology 201
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Chapter 03
Lecture and Animation Outline
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The Chemical BuildingBlocks of Life
Chapter 3
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Carbon
• Framework of biological molecules consists primarily of carbon bonded to – Carbon– O, N, S, P or H
• Can form up to 4 covalent bonds• Hydrocarbons – molecule consisting only
of carbon and hydrogen– Nonpolar– Functional groups add chemical properties
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Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Hydroxyl
Carbonyl
Carboxyl
Amino
Sulfhydryl
Phosphate
Methyl
Example
OH
O
C
O
OH
C
H
H
N
S H
O
proteins
proteinsH
H
Glycerol phosphate
Alanine
Cysteine
Alanine
Acetic acid
Acetaldehyde
Ethanol
COOH
NH2
HH
H
HH
C OHC
O
H C C
H
H
H
H CO
OHH
C
O H
NH
HCH3
H C HSCH2
NH2
OH OH H
P
O
P O–
O–
O
OCCCH
H H H
O H
HO C C
H C H
H
O–
O–
H
C
HO C C
H
FoundIn
carbo-hydrates,proteins,nucleicacids,lipids
carbo-hydrates,nucleicacids
proteins,lipids
proteins,nucleicacids
nucleicacids
FunctionalGroup
StructuralFormula
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Isomers
• Molecules with the same molecular or empirical formula– Structural isomers– Stereoisomers – differ in how groups attached
• Enantiomers– mirror image molecules– chiral– D-sugars and L-amino acids
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C
W
Y
W
Y
C
Z
X
Z
X
Mirror
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Macromolecules
• Polymer – built by linking monomers• Monomer – small, similar chemical subunits
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Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
O
P
P
OH
HO
H
OH
H
OHOH
HH
H
O
Cellular Structure Polymer Monomer
Chromosome DNA strand Nucleotide
MonosaccharideStarchStarch grains in a chloroplast
5-carbon sugarPhosphate
group
Nitrogenous base
CH2OH
Car
bohy
drat
eN
ucle
ic A
cid
P
P
P
PP
P
P
G
C
T
A
A
T
P
A
P
P
P
P
G
C
P
P
T
A
G
C
P
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AlaAla
ValVal
Ser ON
HC
H
OHH
CCH3
Intermediate filament Polypeptide Amino acid
Prot
ein
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HO H H H H H H H H H HHHO C C C C C C C C C C C C
H H H H H H H H H H H
Adipose cell with fat dropletsTriglyceride
Fatty acid
Lipi
d
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• Dehydration synthesis– Formation of large molecules by the removal of water– Monomers are joined to form polymers
• Hydrolysis– Breakdown of large molecules by the addition of
water– Polymers are broken down to monomers
HO
HO H
HO HH HHO
HO H HHO
a. Dehydration reaction b. Hydrolysis reaction
H2O H2O
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Carbohydrates
• Molecules with a 1:2:1 ratio of carbon, hydrogen, oxygen
• Empirical formula (CH2O)n
• C—H covalent bonds hold much energy– Carbohydrates are good energy storage
molecules– Examples: sugars, starch, glucose
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Monosaccharides
• Simplest carbohydrate• 6 carbon sugars play important roles• Glucose C6H12O6
• Fructose is a structural isomer of glucose• Galactose is a stereoisomer of glucose• Enzymes that act on different sugars can
distinguish structural and stereoisomers of this basic six-carbon skeleton
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H
CH2OH
H
OH
OH HH
H
C
CC
C
C
C
C
H
C H
HO
OHH
OHH C
OHH C
OHH C
H
OH
C HH
OH
H
OH
H
OH
H
OH
H
OH HH
H
C
CC
C
C O
OH
OH HH
H
C
CC
C
OC
OH
OH
O
H23
5
14
6
5
4
3
2
1
23
5
6
14
23
5
14
α-glucose or
β-glucose
OO
CH2OH
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Fructose Glucose Galactose
H OH
O
C
C
C
C
C
C
H
H
HO H
H OH
H OH
H OH
H
OC
C
C
C
C
H
H
HO H
OH
H OH
H OH
OC
C
C
C
C
C
H
H
H
HO H
OH
H OH
H OH
CH OH HO H
Stereo-isomer
Structuralisomer
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Disaccharides
• 2 monosaccharides linked together by dehydration synthesis
• Used for sugar transport or energy storage• Examples: sucrose, lactose, maltose
OH
SucroseFructoseα-glucose
HO
CH2OH
H
OH
H
OHH
H
H
O
H
OH H
HO
HO
H
OH
H
OH OHH
H
O
H OH
OH H
HO
+
a. b.Maltose
HO
H
OH
H
OH OHH
H
O H
OH
H
OHOH
HH
H
O
OHHO
H2O
CH2OH CH2OH CH2OH CH2OH CH2OH
CH2OH CH2OH
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Polysaccharides
• Long chains of monosaccharides– Linked through dehydration synthesis
• Energy storage– Plants use starch– Animals use glycogen
• Structural support– Plants use cellulose– Arthropods and fungi use chitin
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Glycogen
Amylose + Amylopectin
b.
a. c. 3.3 µm
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α-glucose
HO
CH2OH
H
OH
H
OH HH
H
O
OH4 1
α-1 4 linkages
CH2OH
OH
H
OH H
H
OCH2OH
OH
H
OH H
H
OCH2OH
OH
H
OH H
H
O
O O
H
α-1 4 linkage
a-1
CH2OH
O
H
OH
H
OH HH
H
O
CH2
H
OH
H
OH HH
H
O
O
CH2OH
H
OH
H
OH HH
H
O
6 linkage
b: © Asa Th oresen/Photo Researchers, Inc.; c: © J. Carson/Custom Medical Stock Photo
7.5 µm
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HO
CH2OH
H
OH
H
OH HH
H
OCH2OH
H H
OH
H
OH HH
H
O
O
CH2OH
H
OH
H
OH HH
H
OOHH
HOH HH
CH2OHO
β-1 4 linkages
OH O O
O4 1
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
b: © Science VU/Visuals Unlimited
β-glucose
500 µmb.
a.
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Nucleic acids
• Polymer – nucleic acids• Monomers – nucleotides
– sugar + phosphate + nitrogenous base– sugar is deoxyribose in DNA or ribose in RNA– Nitrogenous bases include
• Purines: adenine and guanine• Pyrimidines: thymine, cytosine, uracil
– Nucleotides connected by phosphodiester bonds
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5 ́
28
7 6
394
5
1
NH2
O
P
O-
–O O CH2
Phosphate group
Sugar
Nitrogenous base
OH
NN
N
O
4 ́ 1 ́
2 ́3 ́
H in DNA
OH in RNA
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5′
3′
P
P
P
P
OH
Phosphate group
O
O
NH2CC
NN
N
C
HN
CCH
O
H
H
OC
NC
H
N
CNH2
H
CH
a.
b.O
O
O
C
NC
H
N
CH3C
CH
H
O
O
C
NC
H
N
CH
CH
CC
NN
N
C
HN
CCH
H
O
4′
5′
1′
3′ 2′
4′
5′
1′
3′ 2′
4′
5′
1′
3′ 2′
4′
5′
1′
3′ 2′
Phosphodiester bonds
5-carbon sugar
Nitrogenousbase
NH2
GuanineAdenine
Purin
esPy
rimid
ines
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Cytosine(both DNA and RNA)
Thymine(DNA only)
Uracil(RNA only)
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Deoxyribonucleic acid (DNA)
• Encodes information for amino acid sequence of proteins– Sequence of bases
• Double helix – 2 polynucleotide strands connected by hydrogen bonds– Base-pairing rules
• A with T (or U in RNA)• C with G
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5′ end
P
P
P
P
P
C
G
A
A
OH
T
TPhosphodiesterbonds
3′ end
Sugar–phosphate“backbone”
Hydrogenbondsbetween
nitrogenous bases
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Ribonucleic acid (RNA)
• RNA similar to DNA except– Contains ribose instead of deoxyribose– Contains uracil instead of thymine
• Single polynucleotide strand• RNA uses information in DNA to specify
sequence of amino acids in proteins
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Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
P
P
P
P
PPP
P
P
P
P
P
P
P
P
G
C
G
C
T
A
A
A
A
T
T
GBases
Hydrogen bondingOccurs between base-pairs
P
P
PP
P
P
P
G
G
C
A
A
U
U
Bases
Deoxyribose-phosphatebackbone
Ribose-phosphatebackbone
RNA
DNA
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Other nucleotides
• ATP adenosine triphosphate– Primary energy currency of the cell
• NAD+ and FAD+
– Electron carriers for many cellular reactions
4′
56
2
394
8
7
1′
3′ 2′
5′
1
CH2
OOO
O–
OH OH
NH2
N
N
N
N
O
–O O O OP P P
Triphosphate group
5-carbon sugar
O
Nitrogenous base(adenine)
O– O–
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Proteins
Protein functions include:1. Enzyme catalysis 2. Defense3. Transport4. Support5. Motion6. Regulation7. Storage
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• Proteins are polymers– Composed of 1 or more long, unbranched
chains– Each chain is a polypeptide
• Amino acids are monomers• Amino acid structure
– Central carbon atom– Amino group– Carboxyl group– Single hydrogen– Variable R group
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CH2
CH2
CH3
CH2
OH H O
S H
S
CH2
CH2
O
CH2
NH2+
C C O–H3N+
C C O–H3N+
C C O–H3N +
C C O–H3N+
C C O–H3N+
C C O–H3N+
C C O–H3N+
C C O–H3N+C C O–H3N+
C C O–H3N+
C C O–H3N+
C C O–H3N+
C C O–H3N+
C C O–H3N+
C C O–H3N+ C C O–H 3N + C C O–H3N+
C C O–H3N+CH C O– C C O–NH3+
CH3
OH
CH2
OH
OH
H
OH
OH
CH3CH3
CH
CH2
OH
CH3CH3
CH
CH2
OH
NH2O
C
CH2
OH
O–O
C
CH2
CH2
CH2 NH3+
OH
CH2
CH2
CH2
OH
O–O
C
CH2
CH2
OH
NH2O
C
H C CH3
CH2
CH3
OH
H C OH
CH3
OH
CH2
CHC N
HC NH+
H O
HCH2
NHC
H O
CH2
H O
OH
CH2
H O
CH2
CH2
NH
NH2
C
OH
CH2
NH3+
Nonpolar Polar uncharged Charged
Proline(Pro)
Methionine(Met)
Cysteine(Cys)
Tryptophan(Trp)
Tyrosine(Tyr)
Phenylalanine(Phe)
Glycine(Gly)
Leucine(Leu)
Glutamine(Gln)
Isoleucine(Ile)
Asparagine(Asn)
Asparticacid(Asp)
Histidine(His)
Lysine(Lys)
Glutamic acid(Glu)
Threonine(Thr) Arginine
(Arg)
(Ser)Serine
(Ala)Alanine
Non
arom
atic
Aro
mat
icSp
ecia
l fun
ctio
n
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Valine(Val)
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• Amino acids joined by dehydration synthesis– Peptide bond
RH
H
R
H O
R
OH
RH
OH
H2O
H
O
H
OH OH
OHH
CC C C
CC CC
N
N N
NH H
Amino acid
Dipeptide
Amino acid
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4 Levels of structure
• The shape of a protein determines its function
1. Primary structure – sequence of amino acids2. Secondary structure – interaction of groups
in the peptide backbone helix sheet
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4 Levels of structure
3. Tertiary structure – final folded shape of a globular protein
– Stabilized by a number of forces– Final level of structure for proteins consisting
of only a single polypeptide chain
4. Quaternary structure – arrangement of individual chains (subunits) in a protein with 2 or more polypeptide chains
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••••••
••••••
•••
••
•••
•••••••••••••••
•••••••
••••••
••••••
••
•••
•••••••••••••••
••••
Primary Structure
Secondary Structure Secondary Structure
Tertiary Structure Quaternary Structure
N
H
H H
C C C N C C NC
O
O H
OH H
R
R
R
β-pleated sheet α-helix
C
H
R
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The primary structure can foldInto a pleated sheet, or turn into a helix
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Additional structural characteristics
• Motifs – Common elements of secondary structure
seen in many polypeptides– Useful in determining the function of unknown
proteins• Domains
– Functional units within a larger structure– Most proteins made of multiple domains that
perform different parts of the protein’s function34
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Domain 3 Domain 2
Domain 1
DomainsMotifs
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β-α-βmotif
Helix-turn-Helixmotif
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• Once thought newly made proteins folded spontaneously
• Chaperone proteins help protein fold correctly
• Deficiencies in chaperone proteins implicated in certain diseases– Cystic fibrosis is a hereditary disorder
• In some individuals, protein appears to have correct amino acid sequence but fails to fold
Chaperones
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Chance for protein to refold
ADP + P
Cap
ATP
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Correctlyfoldedprotein
Misfoldedprotein
Chaperoneprotein
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Denaturation
• Protein loses structure and function
• Due to environmental conditions– pH– Temperature– Ionic concentration of
solution
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Properly folded protein
Denaturation
Denaturedprotein
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Lipids
• Loosely defined group of molecules with one main chemical characteristic– They are insoluble in water
• High proportion of nonpolar C—H bonds causes the molecule to be hydrophobic
• Fats, oils, waxes, and even some vitamins
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Fats• Triglycerides
– Composed of 1 glycerol and 3 fatty acids• Fatty acids
– Need not be identical– Chain length varies– Saturated – no double bonds between carbon
atoms• Higher melting point, animal origin
– Unsaturated – 1 or more double bonds• Low melting point, plant origin
– Trans fats produced industrially
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C
C
H
HCH
HCH
HOC
HCH CH
HCH
HCH
HCH
HCH
HCH
HCH
CH H
CHC C
HH H HC
HC C
HO
H
HH HCH
HCH
HOC
HCH CH
HCH
HCH
HCH
HCH
HCH
HCH
CH
CHCH
CHH H
CHCH
CH H
OH
H HCH
HCH
HOC
HCH CH
HCH
HCH
HCH
HCH
HCH
HCH
CH H
CH HCH
CH
HC
H HCHH
CH H
CO
OC
HCH
HCH
HCH
HCH CH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
O
OC
HCH
HCH
HCH
HCH CH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
O
OC
HCH
HCH
HCH
HCH CH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
HCH
H
HCH
HCH
H
HCH
HCH
HO
H
H
Structural Formula Structural Formula
Space-Filling Model Space-Filling Model
a. b.
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Phospholipids
• Composed of– Glycerol– 2 fatty acids – nonpolar “tails”– A phosphate group – polar “head”
• Form all biological membranes
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Non
pola
r Hyd
roph
obic
Tai
lsPo
lar H
ydro
phili
c H
eads
Choline
Phosphate
Glycerol
a. b. c. d.
CH2
CH2
CH2H2C
O
OO P
CO O
OO
CH
C
O-
N+(CH3)3
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Fattyacid
Fattyacid
CHCH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3
CHCH2CH2CH2CH2CH2CH2CHCHCH2CH2CH2CH2CH2CH2CH2CH3
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• Micelles – lipid molecules orient with polar (hydrophilic) head toward water and nonpolar (hydrophobic) tails away from water
a.
WaterLipid head(hydrophilic)
Lipid tail(hydrophobic)
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• Phospholipid bilayer – more complicated structure where 2 layers form– Hydrophilic heads point outward– Hydrophobic tails point inward toward each
other
46
b.
Water
Water
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