Tetrazole Photoclick Chemistry:Reinvestigating Its Suitability as aBioorthogonalReaction and Potential Applications
- Tetrazole Photoclick Chemistry:Reinvestigating Its Suitability as aBioorthogonalReaction and Potential Applications
- Zhengqiu Li; Linghui Qian; Lin Li; Jan C. Bernhammer; Han Vinh Huynh; 이준석; Shao Q. Yao
- tetrazole; photochemistry; fluorescence
- Issue Date
- Angewandte Chemie international edition
- VOL 55, NO 6, 2002-2006
- 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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