Synthesis of multivalent neoglyconjugates of MUC1 by the conjugation of carbohydrate-centered, triazole-linked glycoclusters to MUC1 peptides using click chemistry

J Org Chem. 2012 Sep 7;77(17):7564-71. doi: 10.1021/jo3013435. Epub 2012 Aug 17.


The efficient synthesis of multivalent neoglycoconjugates of MUC1 is reported, which utilizes Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuACC) of azide-functionalized GlcNAc-centered neoglycotetrasaccharide clusters to the MUC1 peptide sequence that was equipped with a propargylglycine residue for "click chemistry". In turn the azido-GlcNAc-centered neoglycoclusters were assembled by reaction of a GlcNAc core containing peripheral propargyl functionalities with an appropriate azido-functionalized monosaccharide. The resulting suitably substituted tetrasaccharyl triazole cluster can be easily appended to a range of acetylene-functionalized peptides to produce neoglycoconjugates of biologically important glycopeptides. As proof of principle, the click neoglycoclusters prepared herein were ligated to the MUC1 peptide sequence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Carbohydrates / chemistry*
  • Catalysis
  • Click Chemistry
  • Copper / chemistry
  • Cyclization
  • Glycoconjugates / chemistry*
  • Molecular Conformation
  • Mucin-1 / chemistry*
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Triazoles / chemistry*


  • Alkynes
  • Azides
  • Carbohydrates
  • Glycoconjugates
  • Mucin-1
  • Peptides
  • Triazoles
  • Copper