@article{c88fe7d9d6e14c67af54b89e86f289d1,
title = "Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions",
abstract = "This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized via low-intensity UVA irradiation at physiological pH. Upon isomerization, the triazenes are rendered more basic and readily protonate to release reactive aryl diazonium ions. It was discovered that the intensity and duration of the UV light was essential to the observed diazonium ion reactivity in competition with the traditionally observed photolytic radical pathways. The combination of their synthetic efficiency coupled with their overall stability makes triazenes an attractive candidate for use in bioconjugation applications. Bioorthogonal handles on the triazenes are used to demonstrate the ease by which proteins can be modified. ",
author = "Davis, {Garrett J.} and Townsend, {Julia A.} and Morrow, {Madeline G.} and Mohamed Hamie and Shepard, {Abigail J.} and Hsieh, {Chih Chieh} and Marty, {Michael T.} and Jewett, {John C.}",
note = "Funding Information: This work was supported in part by a National Science Foundation (NSF)-Career Award to J.C.J. (CHE-1552568). Additional funding to J.A.T. and M.T.M. was provided by the National Institute of General Medical Sciences and National Institutes of Health (NIH) (T32 GM008804 to J.A.T. and R35 GM128624 to M.T.M.). All NMR data were collected in the NMR facility at the University of Arizona. The purchase of the Bruker AVANCE III 400 MHz spectrometer was supported by NSF grant 840336 and the University of Arizona. The purchase and upgrade of the Bruker AVANCE DRX 500 MHz spectrometer was partially supported by NSF grant 9214383, the Office of Naval Research, and the University of Arizona. The purchase of the Bruker NEO 500 MHz spectrometer was supported by NSF grant 1920234 and the University of Arizona. All FTIR spectra were collected in the W.M. Keck Center for Nano-Scale Imaging in the Department of Chemistry and Biochemistry at the University of Arizona. This instrument purchase was supported by Arizona Technology and Research Initiative Fund (A.R.S.§15-1648). The gel scanning was accomplished using equipment supported by NIH award S10OD03237. We thank Kristen Keck and Yelena Feinstein at the University of Arizona Analytical & Biological Mass Spectrometry Facility for help with the MS analysis. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",
year = "2021",
month = nov,
day = "17",
doi = "10.1021/acs.bioconjchem.1c00459",
language = "English (US)",
volume = "32",
pages = "2432--2438",
journal = "Bioconjugate Chemistry",
issn = "1043-1802",
publisher = "American Chemical Society",
number = "11",
}