无铜点击化学调控的生色 Sydnone 修饰香豆素
Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry.
机构信息
Institut Européen de Chimie et Biologie , Université de Bordeaux , 2 rue Robert Escarpit , 33607 Pessac , France.
Institut de Neurosciences Cognitives et Intégratives d'Aquitaine , CNRS UMR5287 , Bordeaux , France.
出版信息
Org Lett. 2018 Jul 20;20(14):4213-4217. doi: 10.1021/acs.orglett.8b01587. Epub 2018 Jul 11.
The synthesis, photophysical characterization, and biochemical application of sydnone-modified coumarins, a novel class of fluorogenic clickable reagents, are reported. The sydnone moiety, a stable aromatic 1,3-dipole, efficiently quenched the fluorescence of coumarin, which could be restored, with a 132-fold enhancement, upon cycloadditions with cyclooctynes, thereby expanding the fluorogenic click toolbox. TD-DFT calculations suggest that the fluorescence quenching of the sydnone-modified coumarins is likely due to the presence of an energetically low-lying nonemissive charge-separated state.
报告了西哒诺修饰香豆素的合成、光物理特性和生化应用，香豆素是一类新型的荧光点击试剂。西哒诺部分是一种稳定的芳香 1,3-偶极子，可有效地猝灭香豆素的荧光，而与环辛炔的环加成反应可将其恢复，荧光增强 132 倍，从而扩展了荧光点击工具包。TD-DFT 计算表明，西哒诺修饰香豆素的荧光猝灭可能是由于存在能量较低的非辐射电荷分离态。
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