A CHEMOENZYMIC SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-L-MANNITOL AND 1,5-DIDEOXY-1,5-IMINO-L-RHAMNITOL AND INVESTIGATION OF THEIR EFFECTS ON GLYCOSIDASES

1,5-Dideoxy-1,5-imino-L-rhamnitol (3) and 1,5-dideoxy-1,5-imino-L-mannitol (2), designed as inhibitors of alpha-L-rhamnosidase, have been synthesised from dihydroxyacetone phosphate and 3-azido-2-hydroxypropanal with the aid of partially purified E. coli L-rhamnulose 1-phosphate aldolase free of D-fructose 1,6-bisphosphate aldolase activity. Inhibitory effects of compounds 2, 3, 1,5-dideoxy-1,5-imino-D-mannitol, and 1,5-dideoxy-1,5-imino-D-glucitol (12) were tested on selected glycosidases. It has been found that compound 3 is a good inhibitor of alpha-L-rhamnosidase as well as alpha-L-fucosidases from bovine kidney and epididymis, 2 is a potent inhibitor of alpha-galactosidase and a moderate inhibitor of alpha-L-rhamnosidase, and 12 is a good inhibitor of alpha-galactosidase and alpha-L-rhamnosidase.