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Aryl azides are well-known precursors of nitrenes and have been introduced by Fleet et al. as versatile photoaffinity labeling agents to probe biological receptors.
Aryl azides are well-known precursors of nitrenes and have been introduced by Fleet et al. as versatile photoaffinity labeling agents to probe biological receptors. Upon photolysis, N2 is liberated and a highly unstable singlet Phenylnitrene is being formed in situ, which reacts with neighboring molecules in a variety of reactions. Perfluorophenyl azides, however, form highly stabilized nitrene intermediates that undergo insertion and addition reactions in moderate to good yields rather than intermolecular rearrangements. This type of compounds has been used as photo-cross linker (Lambda max = 258nm) in estrogen receptor studies and for direct surface coating of carbon and organic based polymers.
The field of applications is rather wide, as these compounds can be used for conventional click chemistry applications and also as photo activated linkers for conjugation of small compounds and large biomolecules, as well as for surface functionalization and nanomaterial synthesis.
References:
G.W.J. Fleet, R.R. Porter, J.R. Knowles; Affinity of Antibodies with Aryl Nitrenes as Reactive Group; Nature 1969; 224: 511-512.
Li-Hong Liu, Mingdi Yan; Perfluorophenyl Azides: New Applications in Surface Functionalization and Nanomaterial Synthesis; Accounts of Chemical Research 2011; 43(11): 1434-1443. DOI 10.1021/ar100066t.
Additional References:
Alexander Welle, François Billard, Jacqueline Marchand-Brynaert; Tri- and Tetravalent Photoactivable Cross-Linking Agents; SYNTHESIS 2012; 44: 2249-2254. DOI: 10.1055/s-0031-1290444.
Platz, M. S.; Acc. Chem. Res. 1995; 28: 487.
Pinney, K.G., Katzenellenbogen, J.A.; J. Org. Chem. 1991; 56(9): 3125-3133.
Keana, J.F.W., Cai, S.X.; J. Org. Chem. 1990; 55: 3640-3647.
Hermanson, G.T. (1996). Bioconjugate Techniques. Academic Press: San Diego.
Pandurangi, R.S., et al. Chemistry of bifunctional photoprobes: Part 4: Synthesis of the chromogenic, cleavable, water soluble and heterobifunctional (N-Methyl amino perfluoroaryl azide benzamido)-ethyl-1,3-dithiopropionyl sulfosuccinimide: An efficient protein cross-linking agent. Bioorganic Chem. 1998; 26(4): 201-12.
Pandurangi, R.S., et al. Recent trends in the evaluation of photochemical insertion characteristics of heterobifunctional perfluoroaryl azide chelating agents: Biochemical implications in nuclear medicine. Photochem Photobiol. 1997; 65(2): 208-21.
Pandurangi, R.S., et al. Chemistry of bifunctional photoprobes: Part 1. Perfluoro azido functionalized phosphorus hydrazides as novel photoreactive heterobifunctional chelating agents: High efficiency nitrene insertion on model solvents and proteins. J. Org Chem. 1997; 62(9): 2798-807.
Pandurangi, R.S., et al. Preservation of immunoreactivity in the photolabeling of B72.3 human antibody. Photochem Photobiol. 1996; 64(1): 100-5.
Pandurangi, R.S., et al. Photolabeling of human serum albumin by 4-azido-2-([14C]-methylamino) trifluorobenzonitrile. A high-efficiency long wavelength photolabel. App Rad Isot. 1995; 46(4): 233-9.
Pandurangi, R.S., et al. High efficiency photolabeling of human serum albumin and human γ-globulin with [14C] methyl 4-azido-2,3,5,6-tetrafluorobenzoate. Bioconjugate Chem. 1995; 6: 630-4.
Yan, M., et al. N-Hydroxysuccinimide ester functionalized perfluorophenyl azides as novel photoactive heterobifunctional cross-linking reagents. The covalent immobilization of biomolecules to polymer surfaces. Bioconjugate Chem. 1994; 5: 151-7.
Platz, M.S., et al. Synthesis and binding of new polyfluorinated aryl azides to alpha-chymotrypsin. New reagents for photoaffinity labeling. Bioconjugate Chem. 1993; 4: 256-261.
Platz, M.S., et al. Chemistry and kinetics of singlet (pentafluorophenyl)nitrene. J. Amer Chem Soc. 1992; 114: 5054-67.
Keana, J.F.W., and Cai, S.X.: J. Org. Chem. 1990; 55: 3640-3647.
Kristof De Prijcka, Nele De Smetb, Monika Rymarczyk-Machalb, Gonzalez Van Driesschec, Bart Devreesec, Tom Coenyea, Etienne Schachtb & Hans J. Nelisa; Biofouling: The Journal of Bioadhesion and Biofilm Research 2010; 26(3): 269-275. DOI: 10.1080/08927010903501908.
