快速氧化还原控制自焚硒基半胱氨酸替代物的设计

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-23 DOI:10.1021/acs.orglett.5c0151410.1021/acs.orglett.5c01514

Eliott Roy, Vincent Diemer* and Oleg Melnyk*,

引用次数: 0

摘要

n -硒乙基半胱氨酸衍生物自焚成半胱氨酸表现出很强的索普-英戈尔德效应。值得注意的是，宝石二甲基取代α到硒原子获得了高达252倍的速率加速，使Cys在几分钟内通过C-N键裂解揭开掩膜。这些研究为硒乙基臂分解机制和新的氧化还原敏感的Cys替代物提供了有价值的见解。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Design of Fast Redox-Controlled Self-Immolative Selenium-Based Cysteine Surrogates

查看原文本刊更多论文

Design of Fast Redox-Controlled Self-Immolative Selenium-Based Cysteine Surrogates

The self-immolation of N-selenoethyl cysteine derivatives into cysteine exhibits a strong Thorpe–Ingold effect. Notably, the gem-dimethyl substitution α to the selenium atom achieved rate accelerations up to 252-fold, enabling Cys unmasking through C–N bond cleavage within minutes. These investigations offer valuable insights into the mechanism of selenoethyl arm breakdown and new redox-sensitive Cys surrogates.

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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.