SYNTHESIS OF PHOSPHOROTHIOATE ESTERS OF L-PHENYL-LACTIC ACID AS TRANSITION-STATE INHIBITORS OF CARBOXYPEPTIDASE-A

Diastereoisomeric phosphorothioate diesters and the phosphorothioate m onoester df L-phenyl-lactic acid have been prepared and their inhibito ry properties with carboxypeptidase A investigated. All the phosphorot hioates have K-1-values in the micromolar range, suggesting that neith er the stereochemistry nor additional negative charge on the phosphoro thioate moiety has a major impact on binding.