Bridgehead Alkene-Enabled Strain-Driven Bioorthogonal Reaction

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2022-07-18 DOI:10.1021/acs.orglett.2c01895

Fayang Xie, Haolin Jiang, Xiangqian Jia, Jingyang Zhang, Zhu Zhu, Juanjuan Du* and Yefeng Tang*,

引用次数: 0

Abstract

Herein, we report a novel bioorthogonal reaction that hinges on a bridgehead alkene (BHA)-enabled inverse-electron-demand Diels–Alder (IEDDA) cycloaddition. Readily accessible from natural product β-caryophyllene, the strained BHA displays high reactivity toward the IEDDA reaction while maintaining excellent biocompatibility. The developed IEDDA reaction has been applied to in vitro protein labeling and pretargeted live cell imaging.

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桥头堡烯烃激活菌驱动的生物正交反应

在此，我们报告了一种新的生物正交反应，该反应依赖于桥头堡烯烃(BHA)使能的逆电按需Diels-Alder (IEDDA)环加成。制备的BHA易于从天然产物β-石竹烯中获得，对IEDDA反应具有较高的反应活性，同时保持了良好的生物相容性。开发的IEDDA反应已应用于体外蛋白标记和预靶向活细胞成像。

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.