Castanospermine-trehazolin hybrids: a new family of glycomimetics with tuneable glycosidase inhibitory properties

Chem Commun (Camb). 2002 Apr 21:(8):848-9. doi: 10.1039/b200162d.

Abstract

Bicyclic azasugar glycomimetics related to castanospermine and trehazolin have been prepared from sugar carbodiimides via aminooxazoline intermediates; preliminary enzyme inhibition tests showed a marked dependence of the selectivity and potency towards alpha and beta-glucosidases upon the nature of the exocyclic substituent.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding, Competitive
  • Disaccharides / chemical synthesis*
  • Enzyme Inhibitors / chemical synthesis*
  • Glycoside Hydrolase Inhibitors*
  • Hydrogen-Ion Concentration
  • Indolizines / chemical synthesis*
  • Molecular Structure
  • Plants / enzymology
  • Trehalase / antagonists & inhibitors
  • beta-Glucosidase / antagonists & inhibitors*

Substances

  • Disaccharides
  • Enzyme Inhibitors
  • Glycoside Hydrolase Inhibitors
  • Indolizines
  • trehazolin
  • beta-Glucosidase
  • Trehalase
  • castanospermine