Jun 1, 1976

Stereochemical analysis of the elimination reaction catalyzed by D-amino-acid oxidase

Y F Cheung, C Walsh


The stereochemistry of the intramolecular proton transfer catalyzed by the flavoenzyme, D-amino-acid oxidase, during the elimination reaction of beta-chloro-alpha-amino acid substrates (Walsh et al. (1973), J. Biol. Chem. 248, 1964) has been established. Both D-erythro- and D-threo-2-amino-3-chloro(2-3H) butyrate have been shown to yield (3R)-2-keto (3-3H)-2- butyrate predominantly. Tritium 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 triton transfer (7.2% for the D-erythro- and 2.6% for the D-threo compound) have been measured. Their implications on the mechanism of this unusual elimination reaction are discussed.

Mentioned in this Paper

Molecular Stereochemistry
In Vivo NMR Spectroscopy
D-Amino Acid Dehydrogenase
DAO gene
Structure-Activity Relationship
Plasma Protein Binding Capacity
Triton preparation
Protein Conformation

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