Microwave assisted "click" chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support

J Org Chem. 2006 Jun 9;71(12):4700-2. doi: 10.1021/jo060572n.

Abstract

A versatile approach has been developed for the multiple labeling of oligonucleotides. First, three linkers as a H-phosphonate monoester derivative were condensed on a solid-supported T12 to introduce H-phosphonate diester linkages which were oxidized in the presence of propargylamine. Second, three galactosyl azide derivatives were conjugated to the solid-supported three-alkyne-modified T12 by a 1,3-cycloaddition so-called "click chemistry" in the presence of Cu(I) assisted by microwaves.

MeSH terms

  • Carbohydrates / chemistry*
  • Combinatorial Chemistry Techniques
  • Copper
  • Microwaves
  • Molecular Probes / chemical synthesis
  • Oligonucleotides / chemical synthesis*

Substances

  • Carbohydrates
  • Molecular Probes
  • Oligonucleotides
  • Copper