FURTHER EVIDENCE FOR THE INVOLVEMENT OF A MONOCYCLIC BETA-LACTAM IN THE ENZYMATIC CONVERSION OF DELTA-L-ALPHA-AMINOADIPOYL-L-CYSTEINYL-D-VALINE INTO ISOPENICILLIN-N

被引：18

作者：

BALDWIN, JE ^{[1
]}

BRADLEY, M ^{[1
]}

ADLINGTON, RM ^{[1
]}

NORRIS, WJ ^{[1
]}

TURNER, NJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1991年 / 47卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)90503-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Incubation of delta-L-alpha-aminoadipoyl-L-[3-C-13]cysteinyl-D-[3-H-2]valine with Isopenicillin N Synthase (IPNS) resulted in the observation of a 'shunt metabolite', which we believe is formed from the collapse of an enzyme bound monocyclic beta-lactam intermediate. Chemical studies into the origin of the shunt metabolite suggest its formation occurred after initial beta-lactam ring closure. Further chemical studies on the decomposition pathway of a free thiol monocyclic beta-lactam have indicated it is not the source of the shunt metabolite, as upon decomposition the major product formed retains sulphur in the form of an ene-thiol dehydrocysteine.

引用

页码：457 / 480

页数：24

共 28 条

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