Isostere-Based Design of 8-Azacoumarin-Type Photolabile Protecting Groups: A Hydrophilicity-Increasing Strategy for Coumarin-4-ylmethyls
Isostere-Based Design of 8-Azacoumarin-Type Photolabile Protecting Groups: A Hydrophilicity-Increasing Strategy for Coumarin-4-ylmethyls
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DOI：
10.1021/ol5000583
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发表时间：
2014-02-21
期刊：
影响因子：
5.2
通讯作者：
Tamamura, Hirokazu
中科院分区：
文献类型：
--
作者：
Narumi, Tetsuo;Takano, Hikaru;Tamamura, Hirokazu
描述了8-氮杂香豆素-4-基甲基作为水性光不稳定保护基的开发。该策略的一个关键特征是用酰胺键等排取代Bhc衍生物的C7-C8烯醇双键，导致发色团从香豆素转化为8-氮杂香豆素。这种策略使得显著增强的水溶性和容易的光裂解成为可能。
Described is the development of 8-azacoumarin-4-ylmethyl groups as aqueous photolabile protecting groups. A key feature of the strategy is the isosteric replacement of the C7-C8 enol double bond of the Bhc derivative with an amide bond, resulting in conversion of the chromophore from coumarin to 8-azacoumarin. This strategy makes dramatically enhanced water solubility and facile photocleavage possible.