Late-Stage C–H Functionalization of Dehydroalanine-Containing Peptides with Arylthianthrenium Salts and Its Application in Synthesis of Tentoxin Analogue

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-14 DOI:10.1021/acs.orglett.4c04535

Xing-Xing Ding, Bing-Tong Li, Lin Dong

引用次数: 0

Abstract

Dehydrophenylalanine has a characteristic unsaturated double bond that makes it indispensable in the context of peptides and proteins. In this study, we report the Pd-catalyzed C(sp²)–H arylation of dehydroalanine-containing peptides with arylthianthrenium salts under mild and base free conditions, which provides efficient access to dehydrophenylalanine-containing peptides. This approach enables the efficient coupling of different drug scaffolds and bioactive molecules to the peptides. Remarkably, the method could be used for the concise synthesis of tentoxin and its analogue.

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芳硫蒽盐对含脱氢丙氨酸肽的后期C-H功能化及其在Tentoxin类似物合成中的应用

脱氢苯丙氨酸具有独特的不饱和双键，这使得它在肽和蛋白质中不可或缺。在这项研究中，我们报道了pd催化的含脱氢丙氨酸肽与芳基噻吩盐在温和和无碱条件下的C(sp2) -H芳基化反应，这为含脱氢苯基丙氨酸肽提供了有效的途径。这种方法可以使不同的药物支架和生物活性分子与肽有效地偶联。值得注意的是，该方法可用于简捷合成tentoxin及其类似物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.