A chemoenzymic synthesis of 1,5-dideoxy-1,5-imino-L-mannitol and L-rhamnitol and investigation of their effects on glycosidases

Article abstract of DOI:10.1016/0008-6215(93)84211-N

1,5-Dideoxy-1,5-imino-L-rhamnitol (3) and 1,5-dideoxy-1,5-imino-L-mannitol (2), designed as inhibitors of α-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 α-L-rhamnosidase as well as α-L-fucosidases from bovine kidney and epididymis, 2 is a potent inhibitor of α-galactosidase and a moderate inhibitor of α-L-rhamnosidase, and 12 is a good inhibitor of α-galactosidase and α-L-rhamnosidase. 1,5-Dideoxy-1,5-imino-L-rhamnitol (3) and 1,5-dideoxy-1,5-imino-L-mannitol (2), designed as inhibitors of α-L-rhamnosidase, have been synthesized 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 α-L-rhamnosidase as well as α-L-fucosidases from bovine kidney and epididymis, 2 is a potent inhibitor of α-galactosidase and a moderate inhibitor of α-L-rhamnosidase, and 12 is a good inhibitor of α-galactosidase and α-L-rhamnosidase.