Convenient synthesis of stereospecifically deuteriated glycines from glutamic acid using a combination of enzymatic and chemical methods

Abstract

Chiral glycines (1a) and (1b) have been synthesized starting from stereospecifically deuteriated 4-aminobutanoic acids (3a) and (3b). Enzymatic decarboxylation of (2S)-glutamic acid (2a) in ²H₂O and (2R,S)-[2,4,4-²H₃]glutamic acid (2b)+(2c) in H₂O afforded (3a) and (3b), respectively. Chemical transformations of deuteriated pyrrolidinones (4a) and (4b) afforded stereospecifically labelled glycines (1a) and (1b) in good yields.