Synthesis of DNA-Encoded Macrocyclic Peptides via Visible-Light-Mediated Desulfurative C–C Bond Formation

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-28 DOI:10.1021/acs.orglett.4c04210

Yi Gan, Yumei Zeng, Haojie Guan, Alex Shaginian, Jin Li, Guanyu Yang, Guansai Liu

引用次数: 0

Abstract

DNA-encoded library (DEL) technology has been developed to serve as a practical platform for the discovery of biologically active macrocyclic peptide compounds. However, the cyclization of linear peptides has been widely regarded as the challenging step in the production of macrocyclic peptide DELs. Herein, we describe a novel DNA-compatible macrocyclization strategy, which enables the construction of ring systems via visible-light-mediated desulfurative C–C bond formation. The macrocyclization proceeds smoothly under mild conditions and in a good yield. Moreover, the reaction is compatible with a variety of linear substrates and can thus be employed to generate structurally diverse DNA-encoded macrocycles with various ring sizes.

Abstract Image

查看原文本刊更多论文

通过可见光介导的脱硫 C-C 键形成合成 DNA 编码的大环肽

DNA 编码文库（DEL）技术是发现具有生物活性的大环肽化合物的实用平台。然而，线性肽的环化一直被广泛认为是生产大环肽 DEL 的挑战性步骤。在此，我们介绍了一种新型的 DNA 兼容大环化策略，该策略可通过可见光介导的脱硫 C-C 键形成来构建环状系统。大环化反应在温和的条件下顺利进行，而且收率很高。此外，该反应与多种线性底物兼容，因此可用于生成具有不同环尺寸的结构多样的 DNA 编码大环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.