(3R,4S,5R,6R,7S)-3,4,5,7-Tetrahydroxyconidine, an azetidine analogue of 6,7-diepicastanospermine and a conformationally constrained d-deoxyaltronojirimycin, from l-arabinose

Bioorg Med Chem. 2013 Aug 15;21(16):4813-9. doi: 10.1016/j.bmc.2013.03.004. Epub 2013 Mar 13.

Abstract

The synthesis from l-arabinose of an azetidine analogue of 6,7-diepicastanospermine and its glycosidase inhibition profile are described.

Keywords: 6,7-Diepicastanospermine; Azetidine; Glycosidase inhibition; l-Arabinose.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / chemistry*
  • Arabinose / chemistry*
  • Azetidines / chemical synthesis
  • Azetidines / chemistry*
  • Azetidines / metabolism
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / metabolism
  • Glycoside Hydrolases / antagonists & inhibitors
  • Glycoside Hydrolases / metabolism
  • Indolizines / chemistry*
  • Molecular Conformation
  • Protein Binding
  • Stereoisomerism

Substances

  • 3,4,5,7-tetrahydroxyconidine
  • Azetidines
  • Enzyme Inhibitors
  • Indolizines
  • 1-Deoxynojirimycin
  • azetidine
  • Arabinose
  • Glycoside Hydrolases
  • castanospermine