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Title: Diazoalkane decay kinetics from UVA-active protein labelling molecules : trifluoromethyl phenyl diazirines
Authors: Djordjevic, Ivan
Wicaksono, Gautama
Solic, Ivan
Steele, Terry W. J.
Keywords: Science::Chemistry::Physical chemistry::Photochemistry
Issue Date: 2020
Source: Djordjevic, I., Wicaksono, G., Solic, I., & Steele, T. W. J. (2020). Diazoalkane decay kinetics from UVA-active protein labelling molecules : trifluoromethyl phenyl diazirines. Results in Chemistry, 2, 100066-. doi:10.1016/j.rechem.2020.100066
Journal: Results in Chemistry
Abstract: Trifluoromethyl phenyl diazirine (TPD) molecules are relatively stable carbene precursors, that readily form carbon covalent bonds with proteins. The stability of the diazoalkane intermediates is unknown, as are the factors which control carbene/diazoalkane ratios. This leads to incomplete carbene insertion onto desired compounds. Herein, stability and decay kinetics of diazoalkanes are evaluated from TPDs with various electron drawing groups, including 3-Phenyl-3-(trifluoromethyl)-3H-diazirine (TPD-H), p-benzyl alcohol (TPD-CH2OH), p-4benzoic acid (TPD-COOH), and p-benzyl bromide (TPD-CH2Br). The spectroscopic analysis before and after UVA activation is performed both in dilute chloroform and neat by 19F NMR and ATR-FTIR, respectively. The increase of diazoalkane concentration after UVA exposure was in the order of: TPD-H > TPD-CH2Br > TPDCH2OH>TPD-COOH. Indirect carbene/diazoalkane ratios ranged from 6: 1 to 3:1. Diazoalkanewas relatively stable over the evaluation period of 30 min (post-UVA activation) in all compounds except TPD-CH2Br, which exhibits an 11 min half-life.
ISSN: 2211-7156
DOI: 10.1016/j.rechem.2020.100066
Rights: © 2020 The Author(s). Published by Elsevier B.V. This is an open access article under the CC BY license (
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:MSE Journal Articles

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