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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.
Research output not available from this repository, contact author.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: |
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| Number: | 1 | ||||
| Number of Pages: | 10 | ||||
| Page Range: | pp. 53-62 | ||||
| Publication Status: | Published |
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