Studies on Angiotensin‐Converting Enzyme Inhibitors: Protease Catalyzed Resolution of Aryl 3‐Mercapto‐2‐Methylpropionic Ester

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Optically active 3‐benzylthio‐2‐methylpropionic acid and 3‐benzoylthio‐2‐methylpropionic acid have been prepared via protease‐catalyzed hydrolysis of their corresponding ester and thioester. Subtilisin catalyzed the hydrolysis of the thioester of methyl 3‐benzoylthio‐2‐methylpropionate twice as fast as that of the methyl ester derivative. The stability of the enzyme in organic cosolvents was studied. Immobilization of subtilisin on the solid support XAD‐8 improved the stability of the enzyme. A practical preparative resolution of the title compound is reported.