Enzyme-catalyzed synthesis of 1-deoxymannojirimycin, 1-Ddeoxynojirimycin, and 1,4-Dideoxy-1,4-imino-D-arabinitol

Abstract

The title compounds 1, 2, and 3 are highly effective glycosidase inhibitors. They were synthesized from achiral starting compounds by enzyme-catalyzed CC coupling of dihydroxyacetone phosphate (1, 2) or hydroxypyruvate (3) with racemic 3-azido-2-hydroxypropanal via fructose, sorbose and xylulose derivatives and their subsequent enantioselective catalytic hydrogenation.