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Molecules 2016, 21(10), 1393; doi:10.3390/molecules21101393

Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction

1,2
and
2,*
1
School of Life Sciences, Peking University, Beijing 100871, China
2
National Institute of Biological Sciences, Beijing 102206, China
*
Author to whom correspondence should be addressed.
Academic Editor: James Crowley
Received: 29 September 2016 / Revised: 14 October 2016 / Accepted: 15 October 2016 / Published: 24 October 2016
(This article belongs to the Special Issue Recent Advances in CuAAC Click Chemistry)
View Full-Text   |   Download PDF [3330 KB, uploaded 24 October 2016]   |  

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. View Full-Text
Keywords: CuAAC; click reaction; bioorthogonal reactions; imaging; activity-based protein profiling CuAAC; click reaction; bioorthogonal reactions; imaging; activity-based protein profiling
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Li, L.; Zhang, Z. Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction. Molecules 2016, 21, 1393.

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