title: Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition.
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.
authors.affiliation: Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Timothy R
authors.initials: TR
authors.lastname: Chan
authors.forename: Robert
authors.initials: R
authors.lastname: Hilgraf
authors.forename: Valery V
authors.initials: VV
authors.lastname: Fokin
authors.forename: K Barry
authors.initials: KB
authors.lastname: Sharpless
authors.forename: M G
authors.initials: MG
authors.lastname: Finn
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001393:Azoles / Q000138:chemical synthesis*; D036022:Capsid Proteins / Q000737:chemistry*; D002384:Catalysis; D017798:Comovirus / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration
chemical_list: D000480:Alkynes; D001386:Azides; D001393:Azoles; D036022:Capsid Proteins; D003300:Copper