Visible-light mediated selective phosphonylation modification of tryptophan residues in oligopeptides,Organic Chemistry Frontiers

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Visible-light mediated selective phosphonylation modification of tryptophan residues in oligopeptides
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-08-01 , DOI: 10.1039/d4qo01028k
Wenfang Xiong ₁ , Junye He ₁ , Jinyao Liu ₁ , Peiru Chen ₁ , Shiqi Xu ₁ , Yipeng Liu ₁ , Shiting Chen ₁ , Yuanyuan You ₁ , Zhenyu Chen ₁ , Jinwu Zhao ₁

Affiliation

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.

中文翻译：

可见光介导的寡肽中色氨酸残基的选择性磷酸化修饰

尽管它们在生物和药物化学领域具有重要意义，但生物分子的位点选择性和多样化修饰的困难对其应用造成了巨大障碍。在这里，我们开发了一种由可见光驱动的直接C2-H磷酸化策略，用于在极其温和的条件下对含色氨酸的肽进行特异性修饰，为制备大量磷酸化的含色氨酸肽提供了一种简单且环保的合成方法。重要的是，该协议适用于将磷酸基序安装到天然肽、segtalin A 和 B 中，并且通过 CCK-8 测定，与原始 segtalins 相比，它们的磷酸化肽对 HCT116 和 HepG-2 表现出更好的抗增殖活性。

更新日期：2024-08-06

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