title: Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactone.
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.
authors: Department of Pharmaceutical Sciences, University of Nottingham, University Park, United Kingdom.
authors: S R
authors: SR
authors: Chhabra
authors: P
authors: P
authors: Stead
authors: N J
authors: NJ
authors: Bainton
authors: G P
authors: GP
authors: Salmond
authors: G S
authors: GS
authors: Stewart
authors: P
authors: P
authors: Williams
authors: B W
authors: BW
authors: Bycroft
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D015780:Carbapenems / Q000096:biosynthesis*; D002851:Chromatography, High Pressure Liquid; D006706:Homeostasis / Q000187:drug effects; D009154:Mutation; D016973:Pectobacterium carotovorum / Q000187:drug effects / Q000378:metabolism*
chemical_list: D015780:Carbapenems; C030654:N-(3-oxohexanoyl)-3-aminodihydro-2(3H)-furanone; D015107:4-Butyrolactone