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Trifluoromethyl phenyl diazirine maleimide
Trifluoromethyl phenyl diazirine maleimide is an excellent building block to develop photoactive probes by reacting with a thiol-containing biomolecule. Trifluoromethylphenyldiazirines are one type of the most effective diazirines with generally high photoreaction reaction yield by UV irradiation (~350 nm). Diazirines are known for their ability to undergo photochemical reactions when exposed to ultraviolet (UV) light, specifically by forming highly reactive carbene intermediates that react with nearby molecules. The phenylcarbenes generated by the UV irradiation of trifluoromethylphenyldiazirines have much higher reactivity than nitrenes (generated by phenylazides). Phenylcarbene is incactivated by water when neighboring target molecules are absent, and thus does not lead to non-specific crosslinking. This property makes diazirines useful for studying protein-protein, protein-nucleic acid interactions, ligand-receptor binding, and other biomolecular interactions.
References
View all 7 references: Citation Explorer
Synthetic routes to trifluoromethylphenyl diazirine photolabeling reagents containing an alkyne substituent (TPDYNE) for chemical biology applications.
Authors: Qian, Mingxing and Xu, Yuanjian and Covey, Douglas F
Journal: RSC advances (2023): 36484-36492
Authors: Qian, Mingxing and Xu, Yuanjian and Covey, Douglas F
Journal: RSC advances (2023): 36484-36492
Validation of Trifluoromethylphenyl Diazirine Cholesterol Analogues As Cholesterol Mimetics and Photolabeling Reagents.
Authors: Krishnan, Kathiresan and Qian, Mingxing and Feltes, McKenna and Chen, Zi-Wei and Gale, Sarah and Wang, Lei and Sugasawa, Yusuke and Reichert, David E and Schaffer, Jean E and Ory, Daniel S and Evers, Alex S and Covey, Douglas F
Journal: ACS chemical biology (2021): 1493-1507
Authors: Krishnan, Kathiresan and Qian, Mingxing and Feltes, McKenna and Chen, Zi-Wei and Gale, Sarah and Wang, Lei and Sugasawa, Yusuke and Reichert, David E and Schaffer, Jean E and Ory, Daniel S and Evers, Alex S and Covey, Douglas F
Journal: ACS chemical biology (2021): 1493-1507
A trifluoromethylphenyl diazirine-based SecinH3 photoaffinity probe.
Authors: Albertoni, Barbara and Hannam, Jeffrey S and Ackermann, Damian and Schmitz, Anton and Famulok, Michael
Journal: Chemical communications (Cambridge, England) (2012): 1272-4
Authors: Albertoni, Barbara and Hannam, Jeffrey S and Ackermann, Damian and Schmitz, Anton and Famulok, Michael
Journal: Chemical communications (Cambridge, England) (2012): 1272-4
Affinity-based probes based on type II kinase inhibitors.
Authors: Ranjitkar, Pratistha and Perera, B Gayani K and Swaney, Danielle L and Hari, Sanjay B and Larson, Eric T and Krishnamurty, Ratika and Merritt, Ethan A and Villén, Judit and Maly, Dustin J
Journal: Journal of the American Chemical Society (2012): 19017-25
Authors: Ranjitkar, Pratistha and Perera, B Gayani K and Swaney, Danielle L and Hari, Sanjay B and Larson, Eric T and Krishnamurty, Ratika and Merritt, Ethan A and Villén, Judit and Maly, Dustin J
Journal: Journal of the American Chemical Society (2012): 19017-25
Ultrafast spectroscopic study of the photochemistry and photophysics of arylhalodiazirines: direct observation of carbene and zwitterion formation.
Authors: Wang, Jin and Burdzinski, Gotard and Kubicki, Jacek and Platz, Matthew S and Moss, Robert A and Fu, Xiaolin and Piotrowiak, Piotr and Myahkostupov, Mykhaylo
Journal: Journal of the American Chemical Society (2006): 16446-7
Authors: Wang, Jin and Burdzinski, Gotard and Kubicki, Jacek and Platz, Matthew S and Moss, Robert A and Fu, Xiaolin and Piotrowiak, Piotr and Myahkostupov, Mykhaylo
Journal: Journal of the American Chemical Society (2006): 16446-7
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