Bioorganic and Medicinal Chemistry p. 519 - 533 (1997)
Update date:2022-07-30
Topics:
Le Merrer, Yves
Poitout, Lydie
Depezay, Jean-Claude
Dosbaa, Isabelle
Geoffroy, Sabine
Foglietti, Marie-Jose
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 K(i) in the micromolar range.
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