Enantioselective synthesis of a new family of α-L-fucosidase inhibitors

Article abstract of DOI:10.1016/S0040-4039(99)00184-7

Gem-diamine 1-N-iminosugars of L-fucose-type, a new type of glycosidase inhibitor, have been synthesized from D-ribono-γ-lactone, involving the formation of a gem-diamine 1-N-iminopyranose ring by the Mitsunobu reaction of an aminal as a key step. The analogue, (2S,3S,4R,5R)-2-trifluoroacetamido- 5-methylpiperidine-3,4-diol was proved to be an extremely potent inhibitor against α-L-fucosidase (IC₅₀ 3 ngmL^-1, Ki 5x10^-9M).