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Trifluoromethyl phenyl diazirine NHS ester

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. It's important to note that diazirines are highly reactive and can be challenging to handle due to their instability. They require careful storage and handling, typically in a controlled environment.

References

View all 3 references: Citation Explorer
Multiple neurosteroid and cholesterol binding sites in voltage-dependent anion channel-1 determined by photo-affinity labeling.
Authors: Cheng, Wayland W L and Budelier, Melissa M and Sugasawa, Yusuke and Bergdoll, Lucie and Queralt-Martín, María and Rosencrans, William and Rostovtseva, Tatiana K and Chen, Zi-Wei and Abramson, Jeff and Krishnan, Kathiresan and Covey, Douglas F and Whitelegge, Julian P and Evers, Alex S
Journal: Biochimica et biophysica acta. Molecular and cell biology of lipids (2019): 1269-1279
Activity-Dependent Photoaffinity Labeling of Metalloproteases.
Authors: Prely, Laurette and Klein, Theo and Geurink, Paul P and Paal, Krisztina and Overkleeft, Herman S and Bischoff, Rainer
Journal: Methods in molecular biology (Clifton, N.J.) (2017): 103-111
Efficient synthesis of 3-trifluoromethylphenyldiazirinyl oleic acid derivatives and their biological activity for protein kinase C.
Authors: Hashimoto, Makoto and Nabeta, Kensuke and Murakami, Kentaro
Journal: Bioorganic & medicinal chemistry letters (2003): 1531-3
Page updated on February 12, 2025

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Catalog Number39007
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Physical properties

Molecular weight

426.35

Solvent

DMSO

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Freeze (< -15 °C); Minimize light exposure
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