gem-Diamine 1-N-iminosugars of l-fucose-type, the extremely potent l-fucosidase inhibitors Original Research Article

An efficient route from d-ribono-γ-lactone to gem-diamine 1-N-iminosugars of l-fucose-type, a new family of glycosidase inhibitor, has been developed in a formation of a gem-diamine 1-N-iminopyranose ring by the Mitsunobu reaction of an aminal as a key step. The analogues were proved to be the extremely potent inhibitors against α-l-fucosidase (IC50 ∼3 ng mL−1, Ki ∼5×10−9 M). The present study has shown that a cyclic methanediamine generated in media affects glycosidases as a real active-form of the gem-diamine 1-N-iminosugars of l-fucose-type.