AUTOREGULATION OF CARBAPENEM BIOSYNTHESIS IN Erwinia carotovora BY ANALOGUES OF N-(3-OXOHEXANOYL)-L-HOMOSERINE LACTONE

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,...

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Bibliographic Details
Published in:Journal of antibiotics 1993/03/25, Vol.46(3), pp.441-454
Main Authors: CHHABRA, SIRI RAM, STEAD, PAUL, BAINTON, NIGEL J., SALMOND, GEORGE P. C., GORDON S. A. B. STEWART, WILLIAMS, PAUL, BYCROFT, BARRIE W.
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - pharmacology
Carbapenems - biosynthesis
Chromatography, High Pressure Liquid
Erwinia carotovora
Homeostasis - drug effects
Mutation
Pectobacterium carotovorum - drug effects
Pectobacterium carotovorum - metabolism
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Summary: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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.46.441