Three-component synthesis of neoglycopeptides using a Cu(II)-triggered aminolysis of peptide hydrazide resin and an azide-alkyne cycloaddition sequence

Org Lett. 2011 Aug 19;13(16):4336-9. doi: 10.1021/ol201659x. Epub 2011 Jul 18.

Abstract

Copper(II)-induced oxidative aminolysis of hydrazides generates Cu(I), the catalyst of the azide-alkyne cycloaddition. This feature was exploited to design a novel solid phase detaching three-component reaction permitting the conversion of supported peptide hydrazides into 1,2,3-triazole linked C-terminal neoglycopeptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amines / chemistry*
  • Azides / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Glycopeptides / chemical synthesis*
  • Molecular Structure
  • Oxidation-Reduction
  • Peptides / chemistry*
  • Triazoles / chemistry

Substances

  • Alkynes
  • Amines
  • Azides
  • Glycopeptides
  • Peptides
  • Triazoles
  • Copper