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-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 alpha-L-fucosidase (IC50 approximately 3 ng mL(-1), Ki approximately 5 x 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.
Shitara
E
E
Institute of Microbial Chemistry, Tokyo, Japan.
Nishimura
Y
Y
Kojima
F
F
Takeuchi
T
T
D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003959:Diamines / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007097:Imines / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013057:Spectrum Analysis; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
D002241:Carbohydrates; D003959:Diamines; D004791:Enzyme Inhibitors; D007097:Imines; D005644:alpha-L-Fucosidase