Resolution by means of a Micro-organism of Racemic Diaminosuccinic Acid and Determination of its Configuration

Abstract

THE chemical structure of diaminosuccinic acid is analogous to aspartic acid, asparagine, C4-dicarboxylic acids and the other biologically important substances. The acid, however, has not yet been found in Nature, and so has never been fully investigated. In 1925, racemic acid was resolved into its antipodes by Kuhn1, through the morphine salt of N,N′-dibenzoyl diaminosuccinic acid; [α]20 D = − 18.9° (10 per cent hydrochloric acid). Suzuki and Suzuki2 found, during the course of an investigation on the behaviour of micro-organisms towards the acid, that Micrococcus ureae was capable of growing on a medium containing the racemic acid as the sole source of nitrogen, and that about half the amount of racemic acid always remained even after full growth. From these observations the authors considered that the micro-organism preferentially assimilated one of the two optical isomers, and that a non-utilizable antipode could perhaps be isolated from the medium.