Studies of enzyme-mediated reactions. Part 10. Stereochemical course of the dehydrogenation of stereospecifically labelled 1-aminoheptanes by the amine oxidase from rat liver mitochondria (E.C. 1.4.3.4)

Abstract

(1R)- and (1S)-[1-³H₁]aminoheptanes are synthesised by a route which, in the deuterium series, allows direct correlation with the primary standard, monodeuteriosuccinic acid. The amines, thus of proven absolute stereochemistry, are then used as substrates for the monoamine oxidase from rat liver mitrochondria. The results prove that the (Re)-hydrogen (Scheme 1) is stereospecifically removed by the enzyme. Some anomalous values for retention of tritium found in these experiments lead to the studies described in the following paper.