Stereochemical analysis of the elimination reaction catalyzed by D-amino-acid oxidase
- 1 June 1976
- journal article
- research article
- Published by American Chemical Society (ACS) in Biochemistry
- Vol. 15 (11), 2432-2441
- https://doi.org/10.1021/bi00656a029
Abstract
The stereochemistry of the intramolecular proton transfer catalyzed by the flavoenzyme, D-amino-acid oxidase [porcine kidney], during the elimination reaction of .beta.-chloro-.alpha.-amino acid substrates had been established. Both D-erythro- and D-threo-2-amino-3-chloro[2-3H]butyrate yield (3R)-2-keto[3-3H]butyrate predominantly. 3H kinetic isotope effects on the rate of the reaction (4.7 for the D-erythro, and 3.8 for the D-threo compound) and percentages of intramolecular 3H transfer (7.2% for the D-erythro- and 2.6% for the D-threo compound) were measured. Their implications on the mechanism of this reaction are discussed.This publication has 20 references indexed in Scilit:
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