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Diazoalkane decay kinetics from UVA-active protein labelling molecules: Trifluoromethyl phenyl diazirines
Results in Chemistry Pub Date : 2020-08-13 , DOI: 10.1016/j.rechem.2020.100066
Ivan Djordjevic , Gautama Wicaksono , Ivan Solic , Terry W.J. Steele

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-4-benzoic 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 > TPD-CH2OH > TPD-COOH. Indirect carbene/diazoalkane ratios ranged from 6: 1 to 3:1. Diazoalkane was 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.



中文翻译:

UVA活性蛋白标记分子的重氮烷衰变动力学:三氟甲基苯基二嗪

三氟甲基苯基重氮(TPD)分子是相对稳定的卡宾前体,易于与蛋白质形成碳共价键。重氮烷烃中间体的稳定性以及控制卡宾/重氮烷烃比的因素都是未知的。这导致卡宾不完全插入所需化合物中。在此,重氮基烷烃的稳定性和衰变动力学是通过具有各种电子吸收基团的TPD进行评估的,其中包括3-Phenyl-3-(trifluoromethyl)-3H-diazirine(TPD-H),p-苄醇(TPD-CH 2 OH),-4-苯甲酸(TPD-COOH)和-苄基溴(TPD-CH 2 Br)。UVA活化前后的光谱分析均在稀氯仿和纯净氯仿中进行19 F NMR和ATR-FTIR。UVA暴露后重氮烷的浓度增加顺序为:TPD-H> TPD-CH 2 Br> TPD-CH 2 OH> TPD-COOH。卡宾/重氮烷的间接比例为6:1至3:1。在TPD-CH 2 Br以外的所有化合物中,重氮烷在30分钟(UVA活化后)的评估期内相对稳定,半衰期为11分钟。

更新日期:2020-08-13
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