ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY

被引：23

作者：

BALDWIN, JE ^{[1
]}

LYNCH, GP ^{[1
]}

SCHOFIELD, CJ ^{[1
]}

机构：

[1] OXFORD CTR MOLEC SCI,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON | 1992年 / 48卷 / 41期

关键词：

D O I：

10.1016/S0040-4020(01)82003-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Incubation of L-delta-(alpha-aminoadipoyl)-L-(3,3-difluorohomocysteinyl)-D-valine [an analogue of the natural substrate: L-delta-(alpha-aminoadipoyl)-L-(cysteinyl)-D-valine] with isopenicillin N synthase (IPNS) resulted in the production of a thiocarboxylic acid, i.e. both equivalents of the dioxygen cosubstrate were utilised to oxidise a single carbon of the cysteinyl analogue. This result and others are rationalised in terms of mechanistic proposals for the first ring closure by IPNS. The synthesis of L-difluorohomocysteine and related structures, via 3,3-difluoro-beta-lactams, is described.

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页码：9085 / 9100

页数：16

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