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稳定碳自由基介导的芳基噻蒽鎓盐、烯烃与氨基酸/肽衍生物的组装

Stabilized Carbon Radical-Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives.

作者信息

Dong Bo, Qi Weiguan, Chen Yifeng, Zhang Yufei, Gu Shiyu, Zhao Jianlin, Zhou Qingfa, Shen Jian, Xie Lan-Gui

机构信息

National and Local Joint Engineering Research Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210023, P. R. China.

State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing, 210009, P. R. China.

出版信息

Adv Sci (Weinh). 2025 Jan;12(2):e2411579. doi: 10.1002/advs.202411579. Epub 2024 Nov 21.

Abstract

Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide-related compounds. Particularly notable is their application in pharmaceutical development, leveraging site-selective late-stage functionalization. Here, a visible light-induced three-component reaction involving arylthianthrenium salts, amino acid/peptide derivatives, and alkenes are introduced. This approach utilizes captodatively-stabilized carbon radicals to enable radical-radical C─C coupling, effectively constructing complex bioactive molecules. This method offers a promising alternative route for modular synthesis of peptide-derived bio-relevant compounds.

摘要

将氨基酸和肽与生物活性分子高效组装,有助于肽相关化合物多样化文库的模块化和简化合成。它们在药物开发中的应用尤其显著,利用了位点选择性后期功能化。在此,引入了一种涉及芳基噻蒽鎓盐、氨基酸/肽衍生物和烯烃的可见光诱导三组分反应。该方法利用了受给电子基稳定的碳自由基来实现自由基-自由基碳-碳偶联,有效地构建复杂的生物活性分子。该方法为肽衍生的生物相关化合物的模块化合成提供了一条有前景的替代途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f781/11727398/c2375b639b82/ADVS-12-2411579-g001.jpg

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