Molecular Basis for the Enantioselective Ring Opening of β??Lactams Catalyzed by Candida antarctica Lipase B

…, H Grewal, F Fülöp, RJ Kazlauskas

Index: Park, Seongsoon; Forro, Enikoe; Grewal, Harjap; Fueloep, Ferenc; Kazlauskas, Romas J. Advanced Synthesis and Catalysis, 2003 , vol. 345, # 8 p. 986 - 995

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Citation Number: 48

Abstract

Abstract Lipase B from Candida antarctica (CAL-B) catalyzes the slow, but highly enantioselective (E> 200), ring-opening alcoholysis of two bicyclic and two 4-aryl-substituted β-lactams. Surprisingly, the rate of the reaction varies with the nature of the alcohols and was fastest with either enantiomer of 2-octanol. A 0.5-g scale reaction with 2-octanol as the nucleophile in diisopropyl ether at 60 C yielded the unreacted β-lactam in 39–46% yield ( ...