(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.
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Battersby et al. (1976) studied this question.