Centre for Systems Chemistry, Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen, Nijenborgh 4, 9747 AG Groningen (NL), Fax: (+31) 50-3634279.
Chemistry. 2014 Jan 20;20(4):946-51. doi: 10.1002/chem.201304129.
Azobenzenes have been used as photoresponsive units for the control of numerous biological processes. Primary prerequisites for such applications are site-selective incorporation of photoswitchable units into biomolecules and the possibility of using non-destructive and deep-tissue-penetrating visible light for the photoisomerization. Here we report a push-pull azobenzene that readily undergoes a Staudinger-Bertozzi ligation with azide groups, that can be addressed with visible light (>440 nm) and exhibits the solvato- and acidochromism typical for push-pull systems. The thermal relaxation in aqueous environment proceeds on the low-millisecond timescale, thus enabling control over biological processes on similar timescales. The approach is demonstrated in the modification of a quartz surface and in the incorporation of an azobenzene unit into a functional peptide, the third zinc finger in the mammalian factor Sp1.
偶氮苯被用作控制许多生物过程的光响应单元。这种应用的主要前提条件是将光开关单元选择性地掺入生物分子中，以及使用非破坏性和可穿透深层组织的可见光进行光异构化的可能性。在这里，我们报告了一种推拉偶氮苯，它可以与叠氮基团发生斯塔蒂格-伯托齐连接，该连接可以用可见光（>440nm）寻址，并表现出推拉系统的溶剂化和酸致变色。在水相环境中的热弛豫过程发生在低毫秒范围内，从而能够在相似的时间尺度上控制生物过程。该方法在石英表面的修饰和将偶氮苯单元掺入功能肽（哺乳动物因子 Sp1 的第三个锌指）中得到了证明。
