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Studies on Angiotensin‐Converting Enzyme Inhibitors: Protease Catalyzed Resolution of Aryl 3‐Mercapto‐2‐Methylpropionic Ester
Author(s) -
Chen ShuiTein,
Wong ChiHuey
Publication year - 1989
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198900062
Subject(s) - chemistry , subtilisin , hydrolysis , thioester , catalysis , enzyme , protease , organic chemistry , aryl , derivative (finance) , combinatorial chemistry , financial economics , economics , alkyl
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.