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

Article abstract of DOI:10.1002/1099-0690(200103)2001:5<967::AID-EJOC967>3.0.CO;2-J

5a-Carba-α-L-fucopyranosylamine (5), an α-glucosidase inhibitor validamine analog possessing an α-L-fucose-type structure, and four related compounds (4 and 6-8) were synthesized and their glycosidase inhibitory potential determined. Carbafucosylamine has already been shown to possess a specific and very strong inhibitory activity against α-L-fucosidase (K_i = 1.2 × 10^-8 M, bovine kidney). Judging from the activity of the other analogs prepared, this amine might be expected to be a lead compound for development of a new type of α-L-fucosidase inhibitor.