Angewandte Chemie - International Edition, volume 55, issue 6, pages 2002-2006
Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications
Zhengqiu Li
1, 2
,
Linghui Qian
1
,
Lidong Li
3
,
Jan C Bernhammer
1
,
Han Vinh Huynh
1
,
Jun-Seok Lee
4
,
Publication type: Journal Article
Publication date: 2015-12-07
Quartile SCImago
Q1
Quartile WOS
Q1
SJR: 5.300
CiteScore: 26.6
Impact factor: 16.1
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
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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GOST
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Li Z. et al. Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications // Angewandte Chemie - International Edition. 2015. Vol. 55. No. 6. pp. 2002-2006.
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Li Z., Qian L., Li L., Bernhammer J. C., Huynh H. V., Lee J., Yao S. Q. Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications // Angewandte Chemie - International Edition. 2015. Vol. 55. No. 6. pp. 2002-2006.
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TY - JOUR
DO - 10.1002/anie.201508104
UR - https://doi.org/10.1002/anie.201508104
TI - Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications
T2 - Angewandte Chemie - International Edition
AU - Qian, Linghui
AU - Bernhammer, Jan C
AU - Li, Zhengqiu
AU - Li, Lidong
AU - Huynh, Han Vinh
AU - Lee, Jun-Seok
AU - Yao, Shao Q.
PY - 2015
DA - 2015/12/07
PB - Wiley
SP - 2002-2006
IS - 6
VL - 55
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex
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@article{2015_Li,
author = {Linghui Qian and Jan C Bernhammer and Zhengqiu Li and Lidong Li and Han Vinh Huynh and Jun-Seok Lee and Shao Q. Yao},
title = {Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications},
journal = {Angewandte Chemie - International Edition},
year = {2015},
volume = {55},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/anie.201508104},
number = {6},
pages = {2002--2006},
doi = {10.1002/anie.201508104}
}
Cite this
MLA
Copy
Li, Zhengqiu, et al. “Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications.” Angewandte Chemie - International Edition, vol. 55, no. 6, Dec. 2015, pp. 2002-2006. https://doi.org/10.1002/anie.201508104.