Zhang Jie, Gao Yasi, Kang Xueying, Zhu Zhentao, Wang Zhiqian, Xi Zhen, Yi Long
Public Hatching Platform for Recruited Talents and State Key Laboratory of Organic-Inorganic Composites, College of Science, Beijing University of Chemical Technology, Beijing 100029, China.
Org Biomol Chem. 2017 May 16;15(19):4212-4217. doi: 10.1039/c7ob00830a.
The development of efficient bioorthogonal reactions for sensing of endogenous biomolecules and for bioconjugation should be of paramount importance in the field of chemical biology. In this work, the o,o'-difluorinated aromatic azide was firstly employed to develop a new fast-response fluorescent probe 1 for HS detection and for bioorthogonal reactions. Compared with non- and mono-fluorinated probes, 1 showed faster reaction toward HS, the third gasotransmitter, in buffer (pH 7.4), implying that the reaction rate could be enhanced by the dual-fluorine groups. Furthermore, such enhanced reaction rates of 1 were also observed in the Staudinger reaction and strain-promoted azide-alkyne cycloaddition (SPAAC) based on the comparison studies of the non-fluorinated probe. Our results firstly highlight that the o,o'-difluorinated aromatic azide group should be useful for fast bioorthogonal reactions and HS detection.
开发用于内源性生物分子传感和生物共轭的高效生物正交反应在化学生物学领域应具有至关重要的意义。在这项工作中，首次使用邻，邻'-二氟芳基叠氮化物开发了一种用于HS检测和生物正交反应的新型快速响应荧光探针1。与非氟化和单氟化探针相比，1在缓冲液（pH 7.4）中对第三种气体信号分子HS表现出更快的反应，这意味着双氟基团可以提高反应速率。此外，基于非氟化探针的比较研究，在施陶丁格反应和应变促进的叠氮化物-炔烃环加成反应（SPAAC）中也观察到1的反应速率增强。我们的结果首先表明，邻，邻'-二氟芳基叠氮基团可用于快速生物正交反应和HS检测。
