Late-Stage Stitching Enabled by Palladium-Catalyzed Tryptophan C4 Amination: Peptide Ligation and Cyclodimerization

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-11 DOI:10.1021/acs.orglett.4c04610

Yazhou Li, Yu Zhang, Tao Yu, Qiangqiang Chen, Hong Liu, Jiang Wang

引用次数: 0

Abstract

Here, we report on methods for late-stage peptide diversification through palladium-catalyzed site-selective C(sp²)–H amination of tryptophan residues at the C4 position, utilizing tryptophan-amine cross-links. Our strategy enables practical access to C–N bonds, facilitating the construction of cyclopeptides via late-stage cyclodimerization of structurally complex peptides, which poses significant challenges for organic synthesis. The synthetic utility of this protocol is demonstrated through the synthesis of 30- to 38-membered macrocyclic peptides.

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钯催化色氨酸C4胺化的后期拼接：肽连接和环二聚化

在这里，我们报道了通过钯催化C4位置色氨酸残基的位点选择性C(sp2) -H胺化，利用色氨酸-胺交联进行后期肽多样化的方法。我们的策略使C-N键的实际获取成为可能，通过结构复杂肽的后期环二聚化促进环肽的构建，这对有机合成提出了重大挑战。通过合成30- 38元的大环肽，证明了该方案的合成效用。

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.