基于等排体设计的 8-氮杂香豆素型光解保护基团：增加香豆素-4-基甲基亲水性的策略。

Isostere-based design of 8-azacoumarin-type photolabile protecting groups: a hydrophilicity-increasing strategy for coumarin-4-ylmethyls.

机构信息

Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , Chiyoda-ku, Tokyo 101-0062, Japan.

出版信息

Org Lett. 2014 Feb 21;16(4):1184-7. doi: 10.1021/ol5000583. Epub 2014 Feb 4.

Abstract

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.

摘要

描述了 8-氮杂香豆素-4-基甲基作为水相光解保护基团的发展。该策略的一个关键特点是用酰胺键替代 Bhc 衍生物的 C7-C8 烯醇双键，从而使生色团从香豆素转化为 8-氮杂香豆素。该策略使水溶性显著提高和易于光解成为可能。