SYNTHESIS OF THIOSUGARS AS WEAK INHIBITORS OF GLYCOSIDASES

A series of enantiomerically pure thiosugars (1,6-dideoxy-1,6-thio-D-m annitol or L-iditol, 1,5-dideoxy-1,5-thio-L-gulitol or D-glucitol and 2,5-dideoxy-2,5-thio-L-iditol or D-mannitol, and their corresponding s ulfoxide or sulfone) was synthesized via thiocyclization of C-2-symmet ric bis-epoxides, and subsequently followed by ring isomerization in f ew cases. These compounds have been evaluated as inhibitors of several glycosidases (alpha- and beta-D-glucosidases, alpha-D-mannosidase and alpha-L-fucosidase). (C) 1997 Elsevier Science Ltd.