Click glycoconjugation of per-azido- and alkynyl-functionalized beta-peptides built from aspartic acid

Org Biomol Chem. 2010 Jun 28;8(13):2941-55. doi: 10.1039/b923275c. Epub 2010 May 4.

Abstract

Azide- and alkynyl-containing homo-beta(3)-peptides, of up to six residues in length, were synthesised in solution from aspartic acid. Their subsequent conjugation with monosaccharides bearing an azide or a terminal alkyne function was efficiently achieved by copper-mediated cycloadditions leading to two novel families of small glycoclusters. These compounds represent ideal tools to explore carbohydrate-mediated multivalent interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Aspartic Acid / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Copper / chemistry
  • Glycopeptides / chemistry*
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*

Substances

  • Alkynes
  • Azides
  • Glycopeptides
  • Oligopeptides
  • Aspartic Acid
  • Copper