A Fast, Visible-Light-Sensitive Azobenzene for Bioorthogonal Ligation

作者:Poloni Claudia; Szymanski Wiktor; Hou Lili; Browne Wesley R*; Feringa Ben L
来源:Chemistry - A European Journal, 2014, 20(4): 946-951.
DOI:10.1002/chem.201304129

摘要

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 (>440nm) 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.

  • 出版日期2014-1-20