The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
AUTOREGULATION OF CARBAPENEM BIOSYNTHESIS IN Erwinia carotovora BY ANALOGUES OF N-(3-OXOHEXANOYL)-L-HOMOSERINE LACTONE
SIRI RAM CHHABRAPAUL STEADNIGEL J. BAINTONGEORGE P. C. SALMONDGORDON S. A. B. STEWARTPAUL WILLIAMSBARRIE W. BYCROFT
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1993 Volume 46 Issue 3 Pages 441-454

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Abstract

N-(3-Oxohexanoyl)-L-homoserine lactone (HSL) (I) is the autoregulator controlling carbapenem antibiotic biosynthesis in Erwinia carotovora ATCC 39048. The chemical synthesis and biological evaluation of analogues of HSL are described. These include alterations of chirality, side-chain modifications, ring size and ring hetero atom. A number of compounds are reported which are capable of restoring the phenotype to a HSL negative mutant but at higher concentrations than HSL.
A-factor, the autoregulator of streptomycin biosynthesis in Streptomyces griseus, was not active as an inducer of carbapenem biosynthesis in E. carotovora.

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© Japan Antibiotics Research Association
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