Synthesis of azasugars as potent inhibitors of glycosidases Original Research Article

A series of enantiomerically pure azasugars (2,5-dideoxy-2,5-imino-d-mannitol, 1-deoxynojirimycin, 1-deoxymannojirimycin, and related compounds) was synthesized from d-mannitol via aminoheterocyclization of C2-symmetric bis-epoxides and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several glycosidases (α- and β-d-glucosidases, α-d-mannosidase and α-l-fucosidase). Inhibition studies indicate notably that the polyhydroxylated azepanes are inhibitors of glycosidases, with K1 in the micromolar range.