Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition

Qian Wang, Timothy R. Chan, Robert Hilgraf, Valery V. Fokin, K. Barry Sharpless, M. G. Finn

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1313 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3192-3193
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number11
DOIs
Publication statusPublished - 19 Mar 2003
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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    Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., & Finn, M. G. (2003). Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. Journal of the American Chemical Society, 125(11), 3192-3193. https://doi.org/10.1021/ja021381e