Glucoamylase from Rhizopus mold and beta-glucosidase catalysed synthesis of dopamine-D-glucoside was optimized in terms of pH, buffer, enzyme, dopamine concentrations and incubation period in organic media. Under the optimum conditions, beta-glucosidase showed regioselectivity by giving rise to 3-hydroxy4-O-(beta-D-glucopyranosyl)phenylethylamine 5b. Presence of hydroxyl group at 3rd and 4th position of phenyl ring showed only monoglycosylation/arylation products With D-glucose 2, D-galactose 3 and D-mannose 4 for both the enzymes. Synthesized glycosides also exhibited ACE inhibition and antioxidant activities. (C) 2008 Elsevier Inc. All rights reserved.