Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications
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Berichtigung: Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications
- Volume 128Issue 10Angewandte Chemie
- pages: 3310-3310
- First Published online: February 24, 2016
Dr. Zhengqiu Li
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
College of Pharmacy, Jinan University, Guangzhou, 510632 China
Search for more papers by this authorLinghui Qian
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorProf. Dr. Lin Li
Key Laboratory of Flexible Electronics & Institute of Advanced Materials, Nanjing Tech University, Nanjing, 211816 China
Search for more papers by this authorDr. Jan C. Bernhammer
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorProf. Dr. Han Vinh Huynh
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorProf. Dr. Jun-Seok Lee
Molecular Recognition Research Center, Korea Institute of Science and Technology, Department of Biological Chemistry, University of Science & Technology, Republic of Korea
Search for more papers by this authorCorresponding Author
Prof. Dr. Shao Q. Yao
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorDr. Zhengqiu Li
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
College of Pharmacy, Jinan University, Guangzhou, 510632 China
Search for more papers by this authorLinghui Qian
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorProf. Dr. Lin Li
Key Laboratory of Flexible Electronics & Institute of Advanced Materials, Nanjing Tech University, Nanjing, 211816 China
Search for more papers by this authorDr. Jan C. Bernhammer
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorProf. Dr. Han Vinh Huynh
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorProf. Dr. Jun-Seok Lee
Molecular Recognition Research Center, Korea Institute of Science and Technology, Department of Biological Chemistry, University of Science & Technology, Republic of Korea
Search for more papers by this authorCorresponding Author
Prof. Dr. Shao Q. Yao
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorAbstract
The bioorthogonality of tetrazole photoclick chemistry has been reassessed. Upon photolysis of a tetrazole, the highly reactive nitrile imine formed undergoes rapid nucleophilic reaction with a variety of nucleophiles present in a biological system, along with the expected cycloaddition with alkenes. The alternative use of the tetrazole photoclick reaction was thus explored: tetrazoles were incorporated into Bodipy and Acedan dyes, providing novel photo-crosslinkers with one- and two-photon fluorescence Turn-ON properties that may be developed into protein-detecting biosensors. Further introduction of these photo-activatable, fluorogenic moieties into staurosporine resulted in the corresponding probes capable of photoinduced, no-wash imaging of endogenous kinase activities in live mammalian cells.
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