Biosynthesis of the polyether antibiotic monensin-a: stereochemical aspects of the incorporation and metabolism of isobutyrate
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 1002-1004
- https://doi.org/10.1039/c39850001002
Abstract
The incorporation of stereospecifically labelled isotopomers of isobutyrate into monensin-A provides stereochemical and mechanistic information about the bioconversion of isobutyrate into methylmalonyl-CoA and n-butyryl-CoA in Streptomyces cinnamonensis; a rearrangement of isobutyryl-CoA to n-butyryl-CoA occurs without loss of the α-hydrogen, and the carbonyl carbon migrates to the pro-(S) methyl group, and is replaced by a hydrogen atom with overall retention of configuration.Keywords
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