Enzymic synthesis and hydrolytic resolution of alkyl β-d-glucopyranosides

Abstract

Extracellular β-glucosidases from Aspergillus oryzae (two strains), Fusarium oxysporum, Aspergillus terreus and Talaromycesflavus were either induced by cellobiose or 6-deoxyglucose, or produced without induction, i.e., either on casein acid hydrolyzate or on the Sabouraud medium. They were tested to catalyze a stereoselective synthesis of the cis- and trans-isomers of 2-(4-methoxybenzyl)-1-cyclohexyl β-d-glucopyranosides with either d-glucose or phenyl β-d-glucopyranoside as sources of the glucosyl unit. The enzymes also hydrolyzed (resolved) diastereoisomeric mixtures of alkyl β-d-glucopyranosides, which were prepared by the Koenigs–Knorr method from the respective cis- and trans-isomers of 2-(4-methoxybenzyl)-1-cyclohexanol.