title: Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction.
abstract: The emergence of bioorthogonal reactions has greatly broadened the scope of biomolecule labeling and detecting. Of all the bioorthogonal reactions that have been developed, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is the most widely applied one, mainly because of its relatively fast kinetics and high efficiency. However, the introduction of copper species to in vivo systems raises the issue of potential toxicity. In order to reduce the copper-induced toxicity and further improve the reaction kinetics and efficiency, different strategies have been adopted, including the development of diverse copper chelating ligands to assist the catalytic cycle and the development of chelating azides as reagents. Up to now, the optimization of CuAAC has facilitated its applications in labeling and identifying either specific biomolecule species or on the omics level. Herein, we mainly discuss the efforts in the development of CuAAC to better fit the bioorthogonal reaction criteria and its bioorthogonal applications both in vivo and in vitro.
authors: School of Life Sciences, Peking University, Beijing 100871, China. lili0224@nibs.ac.cn.|National Institute of Biological Sciences, Beijing 102206, China. lili0224@nibs.ac.cn.
authors: Li
authors: L
authors: Li
authors: National Institute of Biological Sciences, Beijing 102206, China. zhangzhiyuan@nibs.ac.cn.
authors: Zhiyuan
authors: Z
authors: Zhang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002614:Chelating Agents / Q000737:chemistry*; D057930:Click Chemistry / Q000379:methods; D003300:Copper / Q000737:chemistry* / Q000633:toxicity; D061565:Cycloaddition Reaction; D008055:Lipids / Q000737:chemistry; D009696:Nucleic Acids / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry; D011506:Proteins / Q000737:chemistry; D013194:Staining and Labeling / Q000379:methods*
chemical_list: D000480:Alkynes; D001386:Azides; D002614:Chelating Agents; D008055:Lipids; D009696:Nucleic Acids; D011134:Polysaccharides; D011506:Proteins; D003300:Copper
keywords: CuAAC; activity-based protein profiling; bioorthogonal reactions; click reaction; imaging