Studies of enzyme-mediated reactions. Part VI. Stereochemical course of the dehydrogenation of stereospecifically labelled benzylamines by the amine oxidase from pea seedlings (E.C. 1.4.3.6.)

Abstract

(R)-[methylene-²H₁]Benzylamine has been synthesised and its absolute configuration established by degradation to (2R)-[2-²H₁]glycine. By incubating the corresponding chiral tritiated benzylamines with the amine oxidase from pea seedlings, it has been shown that the pro-S-hydrogen atom is removed stereospecifically from the methylene group in the oxidative deamination of benzylamine to benzaldehyde. The enzyme from pea seedlings is readily isolated and is stable; it is now a valuable reagent for assaying the configurational purity of substances which are chiral owing to isotopic substitution at a methylene residue carrying a primary amino-group.