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

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.

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