Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors

Org Biomol Chem. 2006 May 7;4(9):1653-62. doi: 10.1039/b518117h. Epub 2006 Mar 28.

Abstract

A range of new tetra- and pentahydroxylated seven-membered iminoalditols has been efficiently synthesized from epoxyazepane precursors via nucleophilic opening with hydride or oxygenated species and subsequent hydrogenolysis. One tetrahydroxylated azepane, a ring homologue of deoxymannojirimycin, displays a selective and fairly good inhibition of alpha-L-fucosidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin
  • Azepines / chemistry*
  • Enzyme Inhibitors / chemical synthesis*
  • Epoxy Compounds / chemistry*
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Sugar Alcohols / chemical synthesis
  • alpha-L-Fucosidase / antagonists & inhibitors*

Substances

  • Azepines
  • Enzyme Inhibitors
  • Epoxy Compounds
  • Sugar Alcohols
  • 1-Deoxynojirimycin
  • Glycoside Hydrolases
  • alpha-L-Fucosidase