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

2-(4-Methoxybenzyl)-1-cyclohexyl-beta-D-glucopyranosides (1b and 2b) and 2- (4-methoxybenzyl)-1-cyclohexyl-beta-D-galactopyranosides (1c and 2c), model s for glycosidic juvenogens, were synthesized using either D-glucose or D-g alactose [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-cyclo hexanol (1a and 2a) by either enzymic reverse hydrolysis or transglycosylat ion under both standard heating and microwave irradiation. Commercially ava ilable almond beta-glucosidase (EC 3.2.1.21) or beta-galactosidase (EC 3.2. 1.23) from Escherichia coli were employed using different acetonitrile/wate r mixtures [9/1 (v/v) for the reverse hydrolysis, and 4/1 (v/v) for the tra nsglycosylation].