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Issue 1, 1991
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Stereoelectronic control of the tertiary ketol rearrangement: implications for the mechanism of the reaction catalysed by the enzymes of branched-chain amino acid metabolism, reductoisomerase and acetolactate decarboxylase

Abstract

The alkali-catalysed rearrangement of (R)-[1-13C]-3-hydroxy-3-methylpentan-2-one has been studied. Rearrangement via a transition state having an anti arrangement of C–O bonds was preferred over that with a syn arrangement by a factor of 1.8:1. The result is of interest in relation to the mechanism of action of the enzymes reductoisomerase and acetolactate decarboxylase, both of which are involved in the metabolism of the branched-chain amino acids. The structure and relative configuration of the product 23 of bromolactonisation of N-methacrylolyl L-proline 22 were determined by X-ray crystallographic analysis.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1991, 53-62
Article type
Paper

Stereoelectronic control of the tertiary ketol rearrangement: implications for the mechanism of the reaction catalysed by the enzymes of branched-chain amino acid metabolism, reductoisomerase and acetolactate decarboxylase

D. H. G. Crout, C. R. McIntyre and N. W. Alcock, J. Chem. Soc., Perkin Trans. 2, 1991, 53
DOI: 10.1039/P29910000053

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