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STEREOELECTRONIC CONTROL OF THE TERTIARY KETOL REARRANGEMENT - IMPLICATIONS FOR THE MECHANISM OF THE REACTION CATALYZED BY THE ENZYMES OF BRANCHED-CHAIN AMINO-ACID-METABOLISM, REDUCTOISOMERASE AND ACETOLACTATE DECARBOXYLASE

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UNSPECIFIED (1991) STEREOELECTRONIC CONTROL OF THE TERTIARY KETOL REARRANGEMENT - IMPLICATIONS FOR THE MECHANISM OF THE REACTION CATALYZED BY THE ENZYMES OF BRANCHED-CHAIN AMINO-ACID-METABOLISM, REDUCTOISOMERASE AND ACETOLACTATE DECARBOXYLASE. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (1). pp. 53-62. ISSN 0300-9580.

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Abstract

The alkali-catalysed rearrangement of (R)-[1-C-13]-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.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Journal or Publication Title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Publisher: ROYAL SOC CHEMISTRY
ISSN: 0300-9580
Official Date: January 1991
Dates:
DateEvent
January 1991UNSPECIFIED
Number: 1
Number of Pages: 10
Page Range: pp. 53-62
Publication Status: Published

Data sourced from Thomson Reuters' Web of Knowledge

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