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A new thiol blocking reagent, methylsulfonyl benzothiazole, was discovered. This reagent showed good selectivity and high reactivity for protein thiols.

摘要

一种新的巯基阻断试剂，甲基磺酰基苯并噻唑被发现。该试剂对蛋白质巯基具有良好的选择性和高反应活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87f9/3391333/d370ceb49f82/nihms384472f1.jpg

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Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.甲基磺酰苯并噻唑（MSBT）：一种选择性蛋白质巯基阻断试剂。

Org Lett. 2012 Jul 6;14(13):3396-9. doi: 10.1021/ol301370s. Epub 2012 Jun 8.

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Methylsulfonyl benzothiazoles (MSBT) derivatives: Search for new potential antimicrobial and anticancer agents.甲基磺酰基苯并噻唑（MSBT）衍生物：寻找新型潜在抗菌和抗癌药物。

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A novel practical synthesis of benzothiazoles via Pd-catalyzed thiol cross-coupling.一种通过钯催化硫醇交叉偶联实现苯并噻唑的新型实用合成方法。

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Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry.苯并噻唑类化合物的绿色化学合成研究进展。

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Copper-catalyzed synthesis of benzo[b]thiophenes and benzothiazoles using thiocarboxylic acids as a coupling partner.使用硫代羧酸作为偶联试剂的铜催化苯并[b]噻吩和苯并噻唑的合成。

J Org Chem. 2013 Sep 6;78(17):8898-903. doi: 10.1021/jo401353w. Epub 2013 Aug 28.

8

Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes.使用黄原酸盐作为巯基替代物，通过铜催化的原位生成硫醇，一锅法合成苯并噻唑和苯并噻吩。

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Comparison of N-ethyl maleimide and N-(1-phenylethyl) maleimide for derivatization of biological thiols using liquid chromatography-mass spectrometry.使用液相色谱-质谱法比较 N-乙基马来酰亚胺和 N-(1-苯乙基)马来酰亚胺衍生化生物硫醇。

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Nickel-catalyzed coupling of thiomethyl-substituted 1,3-benzothiazoles with secondary alkyl Grignard reagents.镍催化硫甲基取代的1,3-苯并噻唑与仲烷基格氏试剂的偶联反应。

Chemistry. 2013 Feb 25;19(9):2951-5. doi: 10.1002/chem.201203413. Epub 2013 Jan 25.

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Mapping the cysteine proteome: analysis of redox-sensing thiols.绘制半胱氨酸蛋白质组图谱：氧化还原感应巯基分析。

Curr Opin Chem Biol. 2011 Feb;15(1):103-12. doi: 10.1016/j.cbpa.2010.12.014. Epub 2011 Jan 7.

2

Chemical 'omics' approaches for understanding protein cysteine oxidation in biology.用于理解生物学中蛋白质半胱氨酸氧化的化学“组学”方法。

Curr Opin Chem Biol. 2011 Feb;15(1):88-102. doi: 10.1016/j.cbpa.2010.11.012. Epub 2010 Dec 3.

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The redoxome: Proteomic analysis of cellular redox networks.氧化还原组学：细胞氧化还原网络的蛋白质组分析。

相似文献

1

Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.甲基磺酰苯并噻唑（MSBT）：一种选择性蛋白质巯基阻断试剂。

Org Lett. 2012 Jul 6;14(13):3396-9. doi: 10.1021/ol301370s. Epub 2012 Jun 8.

2

Methylsulfonyl benzothiazoles (MSBT) derivatives: Search for new potential antimicrobial and anticancer agents.甲基磺酰基苯并噻唑（MSBT）衍生物：寻找新型潜在抗菌和抗癌药物。

Bioorg Med Chem Lett. 2017 Mar 1;27(5):1319-1324. doi: 10.1016/j.bmcl.2016.08.032. Epub 2016 Aug 20.

3

A novel practical synthesis of benzothiazoles via Pd-catalyzed thiol cross-coupling.一种通过钯催化硫醇交叉偶联实现苯并噻唑的新型实用合成方法。

Org Lett. 2007 Aug 30;9(18):3687-9. doi: 10.1021/ol7015737. Epub 2007 Aug 9.

4

Recent Advances in Synthesis of Benzothiazole Compounds Related to Green Chemistry.苯并噻唑类化合物的绿色化学合成研究进展。

Molecules. 2020 Apr 5;25(7):1675. doi: 10.3390/molecules25071675.

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Synthesis, structure-activity relationships and preliminary antitumor evaluation of benzothiazole-2-thiol derivatives as novel apoptosis inducers.苯并噻唑-2-硫醇衍生物的合成、构效关系及初步抗肿瘤活性评价

Bioorg Med Chem Lett. 2011 Feb 15;21(4):1097-101. doi: 10.1016/j.bmcl.2010.12.124. Epub 2010 Dec 31.

6

Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor.使用硫醇前体通过芳基卤化物偶联一锅法合成不对称二芳基硫醚的铜催化反应。

Org Lett. 2011 Mar 4;13(5):1008-11. doi: 10.1021/ol103041s. Epub 2011 Jan 27.

7

Copper-catalyzed synthesis of benzo[b]thiophenes and benzothiazoles using thiocarboxylic acids as a coupling partner.使用硫代羧酸作为偶联试剂的铜催化苯并[b]噻吩和苯并噻唑的合成。

J Org Chem. 2013 Sep 6;78(17):8898-903. doi: 10.1021/jo401353w. Epub 2013 Aug 28.

8

Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes.使用黄原酸盐作为巯基替代物，通过铜催化的原位生成硫醇，一锅法合成苯并噻唑和苯并噻吩。

Org Biomol Chem. 2013 Feb 13;11(10):1659-65. doi: 10.1039/c3ob26915a.

9

Comparison of N-ethyl maleimide and N-(1-phenylethyl) maleimide for derivatization of biological thiols using liquid chromatography-mass spectrometry.使用液相色谱-质谱法比较 N-乙基马来酰亚胺和 N-(1-苯乙基)马来酰亚胺衍生化生物硫醇。

Anal Bioanal Chem. 2020 Mar;412(7):1639-1652. doi: 10.1007/s00216-020-02398-x. Epub 2020 Feb 4.

10

Nickel-catalyzed coupling of thiomethyl-substituted 1,3-benzothiazoles with secondary alkyl Grignard reagents.镍催化硫甲基取代的1,3-苯并噻唑与仲烷基格氏试剂的偶联反应。

Chemistry. 2013 Feb 25;19(9):2951-5. doi: 10.1002/chem.201203413. Epub 2013 Jan 25.

引用本文的文献

1

Thiol-thiol cross-clicking using bromo-ynone reagents.使用溴代炔酮试剂进行硫醇-硫醇交叉点击反应。

Nat Commun. 2025 Jul 10;16(1):6386. doi: 10.1038/s41467-025-61682-5.

2

Electron-withdrawing inductive effects enhanced strategy for protein thiol sensing and blocking agent design.用于蛋白质硫醇传感和阻断剂设计的吸电子诱导效应增强策略。

Smart Mol. 2024 Feb 14;2(1):e20230022. doi: 10.1002/smo.20230022. eCollection 2024 Mar.

3

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1

Mapping the cysteine proteome: analysis of redox-sensing thiols.绘制半胱氨酸蛋白质组图谱：氧化还原感应巯基分析。

Curr Opin Chem Biol. 2011 Feb;15(1):103-12. doi: 10.1016/j.cbpa.2010.12.014. Epub 2011 Jan 7.

2

Chemical 'omics' approaches for understanding protein cysteine oxidation in biology.用于理解生物学中蛋白质半胱氨酸氧化的化学“组学”方法。

Curr Opin Chem Biol. 2011 Feb;15(1):88-102. doi: 10.1016/j.cbpa.2010.11.012. Epub 2010 Dec 3.

3

The redoxome: Proteomic analysis of cellular redox networks.氧化还原组学：细胞氧化还原网络的蛋白质组分析。

Methods Mol Biol. 2025;2921:331-344. doi: 10.1007/978-1-0716-4502-4_18.

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Scalable Thiol Reactivity Profiling Identifies Azetidinyl Oxadiazoles as Cysteine-Targeting Electrophiles.可扩展的巯基反应性分析鉴定氮杂环丁烷恶二唑类化合物为半胱氨酸靶向亲电试剂。

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Exploring 2-Sulfonylpyrimidine Warheads as Acrylamide Surrogates for Targeted Covalent Inhibition: A BTK Story.探索 2-磺酰基嘧啶作为针对 BTK 的靶向共价抑制的丙烯酰胺类似物：一个 BTK 的故事。

J Med Chem. 2024 Aug 22;67(16):13572-13593. doi: 10.1021/acs.jmedchem.3c01927. Epub 2024 Aug 9.

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N-Acryloylindole-alkyne (NAIA) enables imaging and profiling new ligandable cysteines and oxidized thiols by chemoproteomics.N-丙烯酰基吲哚-炔 (NAIA) 通过化学生物组学能够对新的可配体半胱氨酸和氧化型硫醇进行成像和分析。

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istegrate (DIN) Theory Enabling Precision Engineering of Proteins.集成（德国工业标准）理论助力蛋白质的精准工程。（注：原文istegrate可能有误，推测为integrate）

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Chembiochem. 2022 Nov 4;23(21):e202200417. doi: 10.1002/cbic.202200417. Epub 2022 Sep 27.

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GAPDH mediates nitrosylation of nuclear proteins.GAPDH 介导核蛋白的硝化。

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GAPDH regulates cellular heme insertion into inducible nitric oxide synthase.GAPDH 调控诱导型一氧化氮合酶的细胞血红素插入。

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Disulfide formation via sulfenamides.通过亚磺酰胺形成二硫键。

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An introduction to methods for analyzing thiols and disulfides: Reactions, reagents, and practical considerations.硫醇和二硫化物分析方法介绍：反应、试剂及实际考量

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Methods for the determination and quantification of the reactive thiol proteome.用于确定和定量反应性巯基蛋白质组的方法。

Free Radic Biol Med. 2009 Sep 15;47(6):675-83. doi: 10.1016/j.freeradbiomed.2009.06.012. Epub 2009 Jun 13.

甲基磺酰苯并噻唑（MSBT）：一种选择性蛋白质巯基阻断试剂。

Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.

机构信息

Department of Chemistry, Washington State University, Pullman, Washington 99164, USA.

出版信息

Org Lett. 2012 Jul 6;14(13):3396-9. doi: 10.1021/ol301370s. Epub 2012 Jun 8.

DOI:10.1021/ol301370s

PMID:22681565

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3391333/

Abstract

A new thiol blocking reagent, methylsulfonyl benzothiazole, was discovered. This reagent showed good selectivity and high reactivity for protein thiols.

摘要

一种新的巯基阻断试剂，甲基磺酰基苯并噻唑被发现。该试剂对蛋白质巯基具有良好的选择性和高反应活性。

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深度研究

甲基磺酰苯并噻唑（MSBT）：一种选择性蛋白质巯基阻断试剂。

Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.

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出版信息

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本文引用的文献

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引用本文的文献

本文引用的文献

甲基磺酰苯并噻唑（MSBT）：一种选择性蛋白质巯基阻断试剂。

Methylsulfonyl benzothiazole (MSBT): a selective protein thiol blocking reagent.

机构信息

出版信息