Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2023-06-29 DOI:10.1021/acs.orglett.3c01817

Yandan Bao, Minyan Xing, Naylor Matthew, Xiaohua Chen, Xuan Wang* and Xiaojie Lu*,

引用次数: 0

Abstract

While DNA-encoded macrocyclic libraries have gained substantial attention and several hit compounds have been identified from DNA-encoded library technology, efficient on-DNA macrocyclic methods are also required to construct DNA-linked libraries with a high degree of cyclization and DNA integrity. In this paper, we reported a set of on-DNA methodologies, including the use of an OPA-mediated three-component cyclization with native handles of amino acids and photoredox chemistries. These chemistries proceed smoothly under mild conditions in good to excellent conversions, successfully generating novel isoindole, isoindoline, indazolone, and bicyclic scaffolds.

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通过三组分环化和光诱导化学实现 DNA 链接肽的大环化

虽然 DNA 编码大环化合物库已受到广泛关注，并已从 DNA 编码库技术中鉴定出若干命中化合物，但还需要高效的 DNA 上大环方法来构建具有高度环化和 DNA 完整性的 DNA 连接库。在本文中，我们报告了一套 DNA 上方法，包括使用 OPA 介导的三组分环化与氨基酸的本机处理和光氧化化学反应。这些化学反应在温和条件下顺利进行，转化率从良好到极佳，成功生成了新型异吲哚、异吲哚啉、吲唑酮和双环支架。

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.