Multivalent iminosugars to modulate affinity and selectivity for glycosidases

Org Biomol Chem. 2009 Jan 21;7(2):357-63. doi: 10.1039/b815408b. Epub 2008 Nov 18.

Abstract

A series of mono-, di- and tri-valent iminosugars based on oligoethylene scaffolds and N-substituted deoxynojirymicin epitopes have been synthesized by "click chemistry" to study the effect of multivalency on glycosidase inhibition. Biological evaluation evidenced differences in the inhibition trends as a function of the enzyme nature. The results demonstrate that multivalency can be used in some case to modulate both the affinity and the selectivity of glycosidase inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / chemistry
  • Glucosamine / analogs & derivatives
  • Glucosamine / chemistry
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Glycoside Hydrolases / chemistry
  • Imino Sugars / chemistry*
  • Structure-Activity Relationship

Substances

  • Imino Sugars
  • deoxynojirimycine
  • 1-Deoxynojirimycin
  • Glycoside Hydrolases
  • Glucosamine