ICIQ - Institute of Chemical Research of Catalonia, the Barcelona Institute of Science and Technology, Avinguda Països Catalans 16, 43007 Tarragona, Spain.
ICREA, Passeig Lluís Companys 23, 08010 Barcelona, Spain.
Org Lett. 2021 Jan 15;23(2):285-289. doi: 10.1021/acs.orglett.0c03735. Epub 2021 Jan 5.
We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical functionalization. This protocol exhibits high chemoselectivity for Trp residues over other amino acids and tolerates biocompatible conditions.
我们报告了一种光化学方法，用于选择性自由基功能化色氨酸（Trp）-含有肽。该方法利用色氨酸单元与吡啶鎓盐之间生成的电子给体-受体复合物的光活性。用弱光（390nm）照射会在目标色氨酸氨基酸附近生成自由基中间体，促进近距离驱动的自由基功能化。该方案对其他氨基酸具有高度的色氨酸残基化学选择性，并能耐受生物相容性条件。
