Synthesis and biological evaluation of alpha-L-fucosidase inhibitors: 5a-carba-alpha-L-fucopyranosylamine and related compounds

5a-Carba-alpha -L-fucopyranosylamine (5), an alpha -glucosidase inhibitor v alidamine analog possessing an alpha -L-fucose-type structure, and four rel ated compounds (4 and 6-8) were synthesized and their glycosidase inhibitor y potential determined. Carbafucosylamine has already been shown to possess a specific and very strong inhibitory activity against alpha -L-fucosidase (K-i = 1.2 x 10(-8) M, bovine kidney). Judging from the activity of the ot her analogs prepared, this amine might be expected to be a lead compound fo r development of a new type of alpha -L-fucosidase inhibitor.