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首页> 外文期刊>Chemistry: A European journal >Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents
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Irreversible Cysteine-Selective Protein Labeling Employing Modular Electrophilic Tetrafluoroethylation Reagents

机译：采用模块化电泳四氟乙基化试剂的不可逆半胱氨酸选择性蛋白标记

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摘要

Fluoroalkylation reagents based on hypervalent iodine are widely used to transfer fluoroalkyl moieties to various nucleophiles. However, the transferred groups have so far been limited to simple structural motifs. We herein report a reagent featuring a secondary amine that can be converted to amide, sulfonamide, and tertiary amine derivatives in one step. The resulting reagents bear manifold functional groups, many of which would not be compatible with the original synthetic pathway. Exploiting this structural versatility and the known high reactivity toward thiols, the new-generation reagents were used in bioconjugation with an artificial retro-aldolase, containing an exposed cysteine and a reactive catalytic lysine. Whereas commercial reagents based on maleimide and iodoacetamide labeled both sites, the iodanes exclusively modified the cysteine residue. The study thus demonstrates that modular fluoroalkylation reagents can be used as tools for cysteine-selective bioconjugation.
机译：基于高效碘的氟代烷基化试剂广泛用于将氟代烷基部分转移到各种亲核试剂中。 然而，转移的组到目前为止已经限于简单的结构图案。 在此报告了一种具有仲胺的试剂，其可以在一步中转化为酰胺，磺酰胺和叔胺衍生物。 所得试剂具有歧管官能团，其中许多不与原始合成途径相容。 利用这种结构多种能力和已知的硫醇的高反应性，新一代试剂用于生物缀合物，用人工复古 - 醛醇酶，含有暴露的半胱氨酸和反应性催化赖氨酸。 而基于马来酰亚胺和碘乙酰胺的商业试剂标记为两个位点，则碘烷完全改性半胱氨酸残基。 因此，研究表明，模块化氟代烷基化试剂可用作半胱氨酸选择性生物缀有的工具。

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  • 来源
    《Chemistry: A European journal》 |2017年第27期|共5页
  • 作者

    Ji?í Václavík; Reinhard Zschoche; Iveta Klimánková; Václav Matou?ek; Petr Beier; Donald Hilvert; Antonio Togni;

  • 作者单位

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Institute of Organic Chemistry and Biochemistry v.v.i. Academy of Sciences of the Czech Republic Flemingovo nám. 2 166 10 Prague (Czech Republic);

    CF Plus Chemicals s.r.o. Kamenice 771/34 625 00 Brno (Czech Republic);

    Institute of Organic Chemistry and Biochemistry v.v.i. Academy of Sciences of the Czech Republic Flemingovo nám. 2 166 10 Prague (Czech Republic);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

    Department of Chemistry and Applied Biosciences Swiss Federal Institute of Technology ETH Zerich Vladimir-Prelog-Weg 2 8093 Zerich (Switzerland);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    bioconjugation; cysteine; enzymes; fluorine; fluoroalkylation; hypervalent iodine;

    机译：生物谐波;半胱氨酸;酶;氟;氟代烷基化;杂种碘;

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