期刊

Organic Chemistry Frontiers

标题

Visible-light mediated selective phosphonylation modification of tryptophan residues in oligopeptides

作者

Wenfang Xiong, Junye He, Jinyao Liu, Peiru Chen, Shiqi Xu, Yipeng Liu, Shiting Chen, Yuanyuan You, Zhenyu Chen and Jinwu Zhao

摘要

Despite their significant importance in biological and medicinal chemistry fields, the difficulties in the site-selective and diverse modification of biomolecules pose substantial obstacles to their applications. Here, we developed a direct C2–H phosphonylation strategy driven by visible light for specific modification of tryptophan containing peptides under exceedingly mild conditions, providing a straightforward and environmentally friendly synthetic method for the preparation of a plethora of phosphorylated tryptophan-containing peptides. Importantly, the protocol is applicable to the late-stage installation of phosphonate motifs into natural peptides, segetalin A and B, and their phosphonylation peptides exhibited better antiproliferative activity against HCT116 and HepG-2 compared with the original segetalins by a CCK-8 assay.

原文链接

https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo01028k