An immobilized and reusable Cu(I) catalyst for metal ion-free conjugation of ligands to fully deprotected oligonucleotides through click reaction

Chem Commun (Camb). 2013 Jan 7;49(2):184-6. doi: 10.1039/c2cc36811k. Epub 2012 Nov 21.

Abstract

Chelation of Cu(I) ions to an immobilized hydrophilic tris(triazolylmethyl)amine chelator on a solid support allowed synthesis of RNA oligonucleotide conjugates from completely deprotected alkyne-oligonucleotides. No oligonucleotide strand degradation or metal ion contamination was observed. Furthermore, use of the immobilized copper(I) ion overcame regioselectivity issues associated with strain-promoted copper-free azide-alkyne cycloaddition.

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Catalysis
  • Chelating Agents / chemistry
  • Click Chemistry
  • Copper / chemistry*
  • Ions / chemistry
  • Ligands
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Polystyrenes / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Azides
  • Chelating Agents
  • Ions
  • Ligands
  • Oligonucleotides
  • Polystyrenes
  • Copper