Resolution of a tetrahydrofuran ester by Candida rugosa lipase (CRL) and an examination of CRL's stereochemical preference in organic media

Abstract

Abstract Crude lipase from Candida rugosa (CRL) is able to resolve the C3-stereoisomers of the furo[2,3b]furan building block methyl 2-methoxytetrahydrofuran-3-carboxylate 6 by alcoholysis using n -butanol in octane. The reaction is not affected by the configuration at C2. The absolute configuration of the product 7 is 3S as determined by X-ray analysis of the crystalline derivative 14 . The stereochemical outcome of the reaction is compared to the active site model derived by the group of Kazlauskas (Ahmed et al., Biocatalysis 9 (1994), 209). Evidence is presented for the validity of this model for CRL-catalyzed alcoholysis, esterification and acidolysis reactions in organic media.