Inactivation of carboxypeptidase a by 2-benzyl-3,4-epithiobutanoic acid

2-Benzyl-3,4-epithiobutanoic acid was designed and synthesized as a pseudomechanism-based inactivator for carboxypeptidase A. Designing rationale, synthesis of racemic 2-benzyl-3,4-epithiobutanoic acid having (2S,3S)- and (2R,3R)-configurations, and inhibitory kinetic parameters and their implications are reported.