Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition

2003/02/22 by Qian Wang, Timothy R. Chan, Robert Hilgraf +3 · 34 citations
Chemistry · Medicine · #Click Chemistry and Applications #Monoclonal and Polyclonal Antibodies Research #Peptidase Inhibition and Analysis

paper · doi:10.1021/ja021381e

Abstract

The copper-catalyzed cycloaddition reaction between azides and alkynes functions efficiently in aqueous solution in the presence of a tris(triazolyl)amine ligand. The process has been employed to make rapid and reliable covalent connections to micromolar concentrations of protein decorated with either of the reactive moieties. The chelating ligand plays a crucial role in stabilizing the Cu(I) oxidation state and protecting the protein from Cu(triazole)-induced denaturation. Because the azide and alkyne groups themselves are unreactive with protein residues or other biomolecules, their ligation is of potential utility as a general bioconjugation method.

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