L-(+)-Cysteine → Isopenicillin N

HRID 482206

反応式

HRID 482206 の反応式
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]

参加物

4

反応物 3

HCID 5862L-(+)-CysteineHCID 6287L-ValineHCID 23664709Penicillin G Potassium

生成物 1

HCID 440723Isopenicillin N

実験手順

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.

出典と根拠

ORDレコード
ord-b8fcb84230e7441a800d7b60a447f963
出典データセット
uspto-grants-1998_08
特許番号
US05795733

関連ノート

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