The biosynthesis of the Streptomyces antibiotic bicyclomycin

被引:9
作者
Bradley, EL
Herbert, RB
Lawrie, KWM
Khan, JA
Moody, CM
Young, DW
机构
[1] SMITHKLINE BEECHAM PHARMACEUT,HARLOW CM19 5AD,ESSEX,ENGLAND
[2] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND
[3] UNIV SUSSEX,SCH CHEM & MOL SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
关键词
D O I
10.1016/0040-4039(96)01521-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bicyclomycin 5 is biosynthesized in Streptomyces sapporonensis from L-leucine 2 and L-isoleucine 1 by way of the naturally occurring diketopiperazine 3 and dihydrobicyclomycin 4. The mode of incorporation of (2S,4R)-[5,5,5-H-2(3)]leucine into 5 (and 4) shows that the entry of the hydroxy group at C-2' occurs with unusual inversion of configuration. The results of inhibition studies permit a useful working hypothesis to be advanced for bicyclomycin biosynthesis. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6935 / 6938
页数:4
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