L-(+)-Cysteine → Isopenicillin N

HRID 376232

Reaction equation

CC1(C)[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][C:14]3C=CC=CC=3)=[O:12])[C:8](=[O:9])N2[C@H]1C([O-])=O.[K+].[NH2:25][C@H:26]([C:29]([OH:31])=[O:30])[CH2:27]S.[NH2:32][C@H:33]([C:37]([OH:39])=[O:38])[CH:34]([CH3:36])[CH3:35]>>[CH3:35][C:34]1([CH3:36])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([CH2:13][CH2:14][CH2:27][C@H:26]([NH2:25])[C:29]([OH:31])=[O:30])=[O:12])[C:8](=[O:9])[N:32]2[C@H:33]1[C:37]([OH:39])=[O:38]

Participants

Reactant 3

HCID 5862L-(+)-Cysteine

HCID 6287L-Valine

HCID 23664709Penicillin G Potassium

Product 1

HCID 440723Isopenicillin N

Procedure

The first two steps in the biosynthesis of penicillin in P. chrysogenum are the condensation of the three amino acids L-5-amino-5-carboxypentanoic acid (L-α-aminoadipic acid) (A), L-cysteine (C) and L-valine (V) into the tripeptide LLD-ACV, followed by cyclization of this tripeptide to form isopenicillin N. This compound contains the typical β-lactam structure.

Sources & evidence

ORD record: ord-adf7e9a585ee43bfafa76483c0e8e2af
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06020151

Linked notes

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