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Discovery of Heteroaromatic Sulfones As a New Class of Biologically Compatible Thiol-Selective Reagents
ACS Chemical Biology ( IF 4 ) Pub Date : 2017-07-19 00:00:00 , DOI: 10.1021/acschembio.7b00444
Xiaofei Chen 1 , Hanzhi Wu 1 , Chung-Min Park 2 , Thomas H. Poole 3 , Gizem Keceli 1 , Nelmi O. Devarie-Baez 1 , Allen W. Tsang 1 , W. Todd Lowther 4 , Leslie B. Poole 4 , S. Bruce King 3 , Ming Xian 2 , Cristina M. Furdui 1
Affiliation  

The selective reaction of chemical reagents with reduced protein thiols is critical to biological research. This reaction is utilized to prevent cross-linking of cysteine-containing peptides in common proteomics workflows and is applied widely in discovery and targeted redox investigations of the mechanisms underlying physiological and pathological processes. However, known and commonly used thiol blocking reagents like iodoacetamide, N-ethylmaleimide, and others were found to cross-react with oxidized protein sulfenic acids (−SOH) introducing significant errors in studies employing these reagents. We have investigated and are reporting here a new heteroaromatic alkylsulfone, 4-(5-methanesulfonyl-[1,2,3,4]tetrazol-1-yl)-phenol (MSTP), as a selective and highly reactive −SH blocking reagent compatible with biological applications.

中文翻译:

杂芳族砜作为一种新型的生物相容的硫醇选择性试剂的发现。

化学试剂与还原的蛋白质硫醇的选择性反应对于生物学研究至关重要。该反应被用来防止常见的蛋白质组学工作流程中的含半胱氨酸的肽发生交联,并广泛用于生理和病理过程机理的发现和靶向氧化还原研究。但是,发现已知和常用的硫醇封闭剂(如碘乙酰胺,N-乙基马来酰亚胺等)与氧化的蛋白质亚磺酸(-SOH)发生交叉反应,从而在使用这些试剂的研究中引入了重大错误。我们已经研究并且在这里报告一种新的杂芳烃烷基砜,4-(5-甲磺酰基-[1,2,3,4]四唑-1-基)-苯酚(MSTP),作为一种选择性和高反应性的-SH封闭剂与生物学应用兼容。
更新日期:2017-07-20
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