Abstract
Almond β-glucosidase was used to catalyze the synthesis of alkyl β-d-glucopyranosides 1b–3b starting from either d-glucose (4) or phenyl-β-d-glucopyranoside (5) and the racemic alcohols 1a–3a. The enzymic reactions were provided in different acetonitrile/water mixtures [9:1 (v/v) for the reverse hydrolysis, and 1:9 (v/v) for the transglycosylation]. Both enzymic reactions, that is, the reverse hydrolysis and the transglucosylation, are enantioselective processes. The enantiomeric purity of products 1b–2b of the enzymic reactions varied between 75 and 86% ee, the values of which were based on the analysis of the aglyconic parts (1c–2c) of the alkyl β-d-glucopyranoside molecules (1b–2b). Chirality 10:676–681, 1998. © 1998 Wiley-Liss, Inc.
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