Synthesis of phosphorothioate esters of L-phenyl-lactic acid as transition-state inhibitors of carboxypeptidase A

Abstract

Diastereoisomeric phosphorothioate diesters and the phosphorothioate monoester of L-phenyl-lactic acid have been prepared and their inhibitory properties with carboxypeptidase A investigated. All the phosphorothioates have K_i-values in the micromolar range, suggesting that neither the stereochemistry nor additional negative charge on the phosphorothioate moiety has a major impact on binding.