Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives,Chemical Communications

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Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives
Chemical Communications ( IF 4.3 ) Pub Date : 2017-10-24 00:00:00 , DOI: 10.1039/c7cc07389e
Samantha Cambray _{1,

2,

3,

4,

5} , Anupam Bandyopadhyay _{1,

2,

3,

4,

5} , Jianmin Gao _{1,

2,

3,

4,

5}

Affiliation

Bioorthogonal fluorogenic reactions serve as enabling tools in research and biotechnology. Herein we describe fluorogenic conjugations of semicarbazide with coumarin derivatives that incorporate a 2-acetylphenylboronic acid motif. These designed coumarins rapidly conjugate with semicarbazide to give diazaborine products with significantly enhanced fluorescence. To demonstrate potential applications of this fluorogenic reaction, we synthesized a semicarbazide-presenting amino acid D-Dap-Scz, which readily incorporates into the cell wall of Staphalococcus aureus and serves as a handle for conjugation with the coumarins. The fluorogenic conjugation of the coumarins to cell surface semicarbazide enables facile visualization of D-Dap-Scz treated bacteria.

中文翻译：

用设计的香豆素衍生物形成氨基脲的氟二氮杂硼嗪形成

正交的荧光反应是研究和生物技术中的辅助工具。在本文中，我们描述了氨基脲与结合了2-乙酰基苯基硼酸基序的香豆素衍生物的荧光共轭。这些设计的香豆素可与氨基脲快速缀合，以提供具有显着增强的荧光的重氮唑啉产品。为了证明该发荧光反应的潜在应用，我们合成了呈现氨基脲的氨基酸D -Dap-Scz，该氨基酸易于并入金黄色葡萄球菌的细胞壁，并用作与香豆素结合的手柄。香豆素与细胞表面半脲的荧光缀合使D -Dap-Scz处理的细菌易于观察。

更新日期：2017-11-21

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