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Dithioesters: simple, tunable, cysteine-selective H2S donors†
Chemical Science ( IF 7.6 ) Pub Date : 2018-11-30 00:00:00 , DOI: 10.1039/c8sc04683b
Matthew M Cerda 1 , Turner D Newton 1 , Yu Zhao 1 , Brylee K Collins 1 , Christopher H Hendon 1 , Michael D Pluth 1
Affiliation  

Dithioesters have a rich history in polymer chemistry for RAFT polymerizations and are readily accessible through different synthetic methods. Here we demonstrate that the dithioester functional group is a tunable motif that releases H2S upon reaction with cysteine and that structural and electronic modifications enable the rate of cysteine-mediated H2S release to be modified. In addition, we use (bis)phenyl dithioester to carry out kinetic and mechanistic investigations, which demonstrate that the initial attack by cysteine is the rate-limiting step of the reaction. These insights are further supported by complementary DFT calculations. We anticipate that the results from these investigations will allow for the further development of dithioesters as important chemical motifs for studying H2S chemical biology.

中文翻译:

二硫酯:简单、可调、半胱氨酸选择性 H2S 供体†

二硫酯在 RAFT 聚合的聚合物化学领域有着丰富的历史,并且可以通过不同的合成方法轻松获得。在这里,我们证明二硫酯官能团是一个可调基序,在与半胱氨酸反应时释放 H 2 S,并且结构和电子修饰使得半胱氨酸介导的 H 2 S 释放速率得以改变。此外,我们使用(双)苯基二硫酯进行动力学和机理研究,结果表明半胱氨酸的初始攻击是反应的限速步骤。这些见解得到了补充 DFT 计算的进一步支持。我们预计这些研究的结果将有助于进一步开发二硫酯作为研究 H 2 S 化学生物学的重要化学基序。
更新日期:2018-11-30
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