Models for glycosidic juvenogens: Enzymic formation of selected alkyl- β -D-glucopyranosides and alkyl- β -D-galactopyranosides under microwave irradiation

Abstract

2-(4-Methoxybenzyl)-1-cyclohexyl-β-d-glucopyra nosides (1b and 2b) and 2-(4-methoxybenzyl)-1-cyclohexyl-β-d-galactopy ranosides (1c and 2c), models for glycosidic juvenogens, were synthesized using either D-glucose or D-galactose [in their natural form (3 and 5) or activated form (4 and 6)], and the respective racemic cis or trans isomers of 2-(4-methoxybenzyl)-1-cyclohexanol (1a and 2a) by either enzymic reverse hydrolysis or transglycosylation under both standard heating and microwave irradiation. Commercially available almond β-glucosidase (EC 3.2.1.21) or β-galactosidase (EC 3.2.1.23) from Escherichia coli were employed using different acetonitrile/water mixtures [9/1 (v/v) for the reverse hydrolysis, and 4/1 (v/v) for the transglycosylation].