A versatile synthetic strategy for the preparation and discovery of new iminocyclitols as inhibitors of glycosidases

A series of iminocyclitols was prepared using a versatile synthetic strateg y, and their inhibition of glycosidases was evaluated using capillary elect rophoresis. The study has demonstrated that remarkable specificities in enz yme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R )-N-methyl-2-(acetamidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine w as found to be very potent; against beta-N-acetylhexosaminidase P with the K-i value of 80 nM.