A versatile synthesis of stereospecificaily labelled D-amino acids and related enzyme inhibitors

Abstract

Stereospecificaily deuteriated isoserines 4, formed from enzymically prepared 3-deuteriated malic acids 2(X = OH) by Curtius rearrangement, have been converted to the deuteriated aziridines 7 and 9 which, on ring-opening and deprotection, yielded samples of the amino acids D-serine and D-cystine and the enzyme inhibitor–substrates D-β-chloroalanine and D-serine O-sulphate which are labelled Stereospecificaily at C-3 with deuterium.