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

Research output: Contribution to journalArticle

1273 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

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Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
Copper
Proteins
Ligands
Denaturation
Triazoles
Biomolecules
Chelation
Amines
Ligation
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. / Wang, Qian; Chan, Timothy R.; Hilgraf, Robert; Fokin, Valery V.; Sharpless, K. Barry; Finn, M. G.

In: Journal of the American Chemical Society, Vol. 125, No. 11, 19.03.2003, p. 3192-3193.

Research output: Contribution to journalArticle

Wang, Q, Chan, TR, Hilgraf, R, Fokin, VV, Sharpless, KB & Finn, MG 2003, 'Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition', Journal of the American Chemical Society, vol. 125, no. 11, pp. 3192-3193. https://doi.org/10.1021/ja021381e
Wang, Qian ; Chan, Timothy R. ; Hilgraf, Robert ; Fokin, Valery V. ; Sharpless, K. Barry ; Finn, M. G. / Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 11. pp. 3192-3193.
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