gem-Diamine 1-N-iminosugars of L-fucose-type, the extremely potent L-fucosidase inhibitors

An efficient route from D-ribono-gamma-lactone to gem-diamine 1-N-iminosuga rs of L-fucose-type, a new family of glycosidase inhibitor, has been develo ped 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 e xtremely potent inhibitors against alpha-L-fucosidase (IC50 similar to 3 ng mL(-1) K-i similar to 5x10(-9) M). The present study has shown that a cycl ic methanediamine generated in media affects glycosidases as a real active- form of the gem-diamine 1-N-iminosugars of L-fucose-type. (C) 2000 Elsevier Science Ltd. All rights reserved.