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

被引:1483
作者
Wang, Q
Chan, TR
Hilgraf, R
Fokin, VV
Sharpless, KB
Finn, MG
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ja021381e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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. Copyright © 2003 American Chemical Society.
引用
收藏
页码:3192 / 3193
页数:2
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