Ruthenium(II)‐Catalyzed Pyridyl‐Directed Tryptophan C−H Acylmethylation with α‐Chloro Ketones

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-02-18 DOI:10.1002/adsc.202400947

Shulei Hu , Yong Wang , Xiong Xie , Renwen Liang , Hong Liu , Jiang Wang

引用次数: 0

Abstract

A ruthenium(II)‐catalyzed C−H acylmethylation of Trp‐containing peptides with α‐chloro ketones is reported here. This reaction features good C‐2 selectivity and chemoselectivity, making it suitable for late‐stage modification of Trp‐containing peptides. Low‐cost metal ruthenium as a catalyst enables the reaction to be conducted on a gram scale. This report also discusses the synthetic applications and presents a method to remove the pyridine directing group. In addition, a plausible mechanism of the C(2)−H acylmethylation reaction is proposed in this article.

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钌(II)催化的吡啶基引导的α-氯酮色氨酸 C-H 乙酰甲基化反应

据报道，钌（Ⅱ）催化的含 Trp 肽与α-氯酮的 C-H酰甲基化反应具有良好的 C-2 选择性和化学选择性，使其适用于含 Trp 肽的后期修饰。该反应具有良好的 C-2 选择性和化学选择性，因此适用于含 Trp 肽的后期修饰。低成本的金属钌作为催化剂，使该反应可以在克级规模上进行。本报告还讨论了合成应用，并介绍了去除吡啶二定向基团的方法。此外，本文还提出了 C(2)-H酰甲基化反应的合理机理。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.