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N-(3-OXOHEXANOYL)-L-HOMOSERINE LACTONE REGULATES CARBAPENEM ANTIBIOTIC PRODUCTION IN ERWINIA-CAROTOVORA
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UNSPECIFIED (1992) N-(3-OXOHEXANOYL)-L-HOMOSERINE LACTONE REGULATES CARBAPENEM ANTIBIOTIC PRODUCTION IN ERWINIA-CAROTOVORA. BIOCHEMICAL JOURNAL, 288 (Part 3). pp. 997-1004. ISSN 0264-6021.
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Abstract
Erwinia carotovora A.T.C.C. 39048 produces the antibiotic 1-carbapen-2-em-3-carboxylic acid. A number of mutants with a carbapenem-non-producing phenotype were selected as part of an investigation into the molecular and genetic basis of carbapenem biosynthesis. Cross-feeding studies revealed that the mutants fell into two discrete groups. Group 1 mutants were found to secrete a diffusible low-molecular-mass compound which restored carbapenem production in group 2 mutants. This compound was isolated from the spent culture supernatant of a group 1 mutant using solvent extraction, hydrophobic-interaction chromatography and silica-gel chromatography, and finally purified by reverse-phase semi-preparative h.p.l.c. M.s. and n.m.r. spectroscopy revealed that the compound was N-(3-oxohexanoyl)homoserine lactone. Both D- and L-isomers were synthesized, and subsequent analysis by c.d. established that the natural product has the L-configuration. Although carbapenem production was restored by both isomers, dose-response curves indicated that the L-isomer has greater activity, with an induction threshold of about 0.5 mug/ml. N-(3-Oxohexanoyl)-L-homoserine lactone is, therefore, an autoregulator of carbapenem biosynthesis rather than a biosynthetic intermediate. This compound is already known for its role in autoinduction of bioluminescence in the marine bacterium Vibrio fischeri. It is also structurally-related to the A- and I-factors which are known to regulate production of antibiotics in some Streptomyces species. Its association in this work with the regulation of carbapenem biosynthesis implies a broader role for autoregulator-controlled gene expression in prokaryotes.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | BIOCHEMICAL JOURNAL | ||||
Publisher: | PORTLAND PRESS | ||||
ISSN: | 0264-6021 | ||||
Official Date: | 15 December 1992 | ||||
Dates: |
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Volume: | 288 | ||||
Number: | Part 3 | ||||
Number of Pages: | 8 | ||||
Page Range: | pp. 997-1004 | ||||
Publication Status: | Published |
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