Norbornene probes for the study of cysteine oxidation
Norbornene probes for the study of cysteine oxidation
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DOI：
10.1016/j.tet.2017.11.011
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发表时间：
2018-03-22
期刊：
影响因子：
2.1
通讯作者：
Chalker, Justin M.
中科院分区：
文献类型：
--
作者：
Alcock, Lisa J.;Farrell, Kyle D.;Chalker, Justin M.
蛋白质上的半胱氨酸残基可以与细胞氧化剂如过氧化氢发生反应。虽然这一过程对清除多余的活性氧很重要，但这种氧化的产物也可能介导细胞信号传导。为了了解半胱氨酸氧化在生物学中的作用，需要选择性探针来检测和量化其发生。半胱氨酸氧化产物如亚磺酸有时是不稳定的，因此寿命很短。如果要分析这种半胱氨酸衍生物，则需要用探针进行快速反应。在这里，我们引入降冰片烯衍生物作为半胱氨酸氧化的探针，并证明了它们捕获亚磺酸的能力。含有炔或生物素亲和标签的降冰片烯衍生物的合成也被报道，以促进这些探针在化学生物学和蛋白质组学中的应用。(C) 2017年作者。Elsevier Ltd.出版。这是一篇基于CC BY许可（http://creativecommons.orgilicensesiby/4.0/）的开放获取文章。
Cysteine residues on proteins can react with cellular oxidants such as hydrogen peroxide. While this process is important for scavenging excess reactive oxygen species, the products of this oxidation may also mediate cell signalling. To understand the role of cysteine oxidation in biology, selective probes are required to detect and quantify its occurrence. Cysteine oxidation products such as sulfenic acids are sometimes unstable and therefore short-lived. If such cysteine derivatives are to be analysed, rapid reaction with the probe is required. Here we introduce norbornene derivatives as probes for cysteine oxidation, and demonstrate their ability to trap sulfenic acids. The synthesis of norbornene derivatives containing alkyne or biotin affinity tags are also reported to facilitate the use of these probes in chemical biology and proteomics. (C) 2017 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.orgilicensesiby/4.0/).