Isolation of 3' -O-acetylchloramphenicol: a possible intermediate in chloramphenicol biosynthesis

Frank Gross; Elizabeth A Lewis; Mahmood Piraee; Karl-Heinz van Pee; Leo C Vining; Robert L White

doi:10.1016/s0960-894x(01)00739-9

Isolation of 3' -O-acetylchloramphenicol: a possible intermediate in chloramphenicol biosynthesis

Bioorg Med Chem Lett. 2002 Feb 11;12(3):283-6. doi: 10.1016/s0960-894x(01)00739-9.

Authors

Frank Gross¹, Elizabeth A Lewis, Mahmood Piraee, Karl-Heinz van Pee, Leo C Vining, Robert L White

Affiliation

¹ Department of Biology, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J1.

PMID: 11814778
DOI: 10.1016/s0960-894x(01)00739-9

Abstract

3' -O-acetylchloramphenicol, commonly formed from chloramphenicol by resistant bacteria, has been isolated from the antibiotic-producing organism. Biosynthetic experiments suggest that it is a protected intermediate in chloramphenicol biosynthesis, implicating acetylation as a self-resistance mechanism in the producing organism.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylation
Anti-Bacterial Agents / biosynthesis*
Chloramphenicol / analogs & derivatives
Chloramphenicol / biosynthesis*
Chromatography, High Pressure Liquid
Hydrolysis
Magnetic Resonance Spectroscopy
Streptomyces / chemistry
Streptomyces / metabolism

Substances

Anti-Bacterial Agents
chloramphenicol 3-acetate
Chloramphenicol