Biosynthetic Pathway of Penicillins

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Biosynthetic pathway of penicillins

NH2 O
H2N H2N
HO + SH +
OH
COOH COOH
O
L--aminoadipic acid L-cysteine L-valine
3 ATP
Mg2+ ACV-synthase
3 AMP + 3 Pi

H SH
H2N N
notice the epimierization of
H L-valine to D-valine
COOH O N
(ACV) O
COOH
Ascorbate isopenicillin N synthase
Fe2+, O2

H H
H2N N S
COOH O N
(isopenicillin N) O COOH

isopenicillin N acyltransferase

NH2 O
HO
OH
O
H
H2N S
OH
N
O O
COOH
phenylacetic acid (PAA)
6-APA
(+)-6-aminopenicillanic acid
phenylacetyl-CoA ligase

CoA

O isopenicillin N acyltransferase

H H
N S
O N
O
COOH
Penicillin G
(benzylpenicillin)

Copyright 2011
Doug E. Frantz, UTSA

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