Michael Addition Reaction between Dehydroalanines and Phosphites Enabled the Introduction of Phosphonates into Oligopeptides

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-05-23 DOI:10.1021/acs.orglett.4c01567

Changjun Yu, Ruiyao E, Yingying An, Xiaomin Guo, Guangjun Bao, Yiping Li, Junqiu Xie and Wangsheng Sun*,

引用次数: 0

Abstract

A method for introducing a range of phosphonates into oligopeptides through a Michael addition reaction between dehydroalanine and phosphite is presented. The method offers a mild, cheap, and straightforward approach to peptide phosphorylation that has potential applications in chemical biology and medicinal chemistry. Moreover, the introduction of a phosphonate group into short antibacterial peptides is described to demonstrate its utility, leading to the discovery of phosphonated antibacterial peptides with potent broad-spectrum antibacterial activity.

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脱氢丙氨酸与亚磷酸盐之间的迈克尔加成反应可将膦酸盐引入寡肽。

本文介绍了一种通过脱氢丙氨酸和亚磷酸酯之间的迈克尔加成反应将一系列膦酸盐引入寡肽的方法。该方法提供了一种温和、廉价、直接的肽磷酸化方法，在化学生物学和药物化学中具有潜在的应用价值。此外，还介绍了在短抗菌肽中引入膦酸基团的方法，以证明该方法的实用性，从而发现了具有强效广谱抗菌活性的膦酸化抗菌肽。

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.