"Click" saccharide/beta-lactam hybrids for lectin inhibition

Org Lett. 2008 Jun 5;10(11):2227-30. doi: 10.1021/ol8006259. Epub 2008 May 9.

Abstract

Hybrid glycopeptide beta-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "click" cycloaddition reaction, and as shown by NMR/MD experiments, binding of the resulting mimetics to Ulex Europaeus Lectin-1 (UEL-1) occurred after a "bent-to-extended" conformational change around a partially rotatable triazolylmethylene moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetic Materials / chemistry
  • Biomimetic Materials / pharmacology
  • Glycopeptides / chemistry*
  • Glycopeptides / pharmacology*
  • Lectins / antagonists & inhibitors*
  • Lectins / chemistry
  • Plant Proteins / antagonists & inhibitors
  • Plant Proteins / chemistry
  • Protein Conformation
  • Ulex / chemistry
  • beta-Lactams / chemistry*
  • beta-Lactams / pharmacology*

Substances

  • Glycopeptides
  • Lectins
  • Plant Proteins
  • beta-Lactams