biosynthesis lecture 1 - introduction to biosynthesis and pharmacognosy

8/10/2019 Biosynthesis Lecture 1 - Introduction to Biosynthesis and Pharmacognosy

1/22

Biosynthesis & Pharmacognosy

CS407

Paraic James 18h

Peter Kenny 18h


2/22

Introduction

Main Biosynthetic Pathways

Biosynthesis o Car!ohydrates "#$ucose%

Pyruate & 'cetate (ormation(atty 'cids

Prostag$andins

Shi)imate'mino 'cids


3/22

'$)a$oids

Mor*hine Biosynthesis

+uc$eotides

Pyrro$e Pigments

'romatic Po$y)etides

,er*enes

Steroids

-Mi.ed/ Pathways

P$ant Sources o rugs

($aanoids

S*ectrosco*ic ,echniues


4/22

Boo)s2

Basic 3rganic Chemistry Part I

,edder5 +echata$5 Murray5 Carndu

3rganic Chemistry

I66(inar

+atura$ Products

J6Mann5 6S6aidson et. al.

Medicina$ +atura$ Products

P6ewic)

3rganic Chemistry o Bio$ogica$ Pathways

McMurry5 Beg$ey


5/22

Biosynthesis

9 Synthesis !y -+ature/

Primary Meta!o$ites & Secondary Meta!o$ites

Proteins ,er*enes

Car!ohydrates Steroids

(atty 'cids '$)a$oids

+uc$eic 'cids "+' etc.%


6/22

Pharmacognosy

-Pharma)on/ #ree) or-:#/

-gnosis/ #ree) or-K+3;


7/22

M'I+ BI3S=+,>


8/22

Glucose

C6H12O6

>AC

3

C33> >AC

3

3>

Pyruic 'cid "CA%

Pyruate C>AC"3%C339

'cetic 'cid "C?%

'cetate C>AC33

9


9/22

A PI+CIP' S,',I+# M',


10/22

'cetate "C?% is a maor Bui$ding B$oc) or2

(',,= 'CIS

P3=K


11/22

'cetate is a$so used to ma)e Mea$onic 'cid "C%

>AC

3

3>

OHHOOC

>AC 3>

Mevalonic Acid


12/22

Mea$onate is is used a !ui$ding !$oc) or2

,


13/22

Pyruate "CA% com!ines with Car!ohydrate

to *roduce2

Shi)imic 'cid "C7%

C33>

3>

>3 OH


14/22

Shi)imate is the *recursor or2

'3M',IC 'MI+3 'CIS

CI++'MIC 'CI


15/22

,here a num!er o routes to ormation o 'mino'cids6

'mino 'cids are im*ortant *recursors or2

'K'3IS

P:I+


16/22


17/22


18/22

C>A

OH

COOH

O3

>AC

3

C33>

>AC 39

O

14C $a!e$$ed 'cetate

6-Methylsalicylic Acid


19/22

a!e$$ed 'cetate *roides a$$ the Car!on in

9Methy$sa$icyc$ic 'cid

"a!e$ inishes u* on eery second Car!on in

a *redicta!$e manner%

Knowing where the $a!e$ was in the starting

materia$ we can *redict where it wi$$ !e in the

*roduct6


20/22

Pro!$ems2

iicu$t to synthesiDe $a!e$$ed *recursors

iicu$t to get good incor*oration o the

$a!e$ into $iing organisms

iicu$ties arise with -di$ution/ o the $a!e$

!y the un$a!e$$ed *oo$

:sua$$y on$y a sma$$ amount o *roduct and

diicu$t to esta!$ish e.act $ocation o the

$a!e$


21/22

'$so diicu$t to esta!$ish the e.act seuence

un$ess the *roducts can !e iso$ated at dierenttime intera$s

A B C

a!e$ wi$$ a**ear in B !eore a**earing in C


22/22

?6 :se '!norma$ -M:,'+,/ systems

B$oc) one ste* o the seuence e6g6 missing

enDyme wi$$ cause !ui$d9u* o the starting

materia$ "B% or that ste* and $ater com*ounds

wi$$ not !e ormed "C%6

A B C

X

biosynthesis lecture 1 - introduction to biosynthesis and pharmacognosy

Documents