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首页> 外文期刊>Chemistry: A European journal >Application of Thiol–yne/Thiol–ene Reactions for Peptide and Protein Macrocyclizations
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Application of Thiol–yne/Thiol–ene Reactions for Peptide and Protein Macrocyclizations

机译：硫醇-yne /硫醇-NEE反应对肽和蛋白质大核含量的应用

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摘要

The application of thiol–yne/thiol–ene reactions to synthesize mono- and bicyclic-stapled peptides and proteins is reported. First, a thiol–ene-based peptide-stapling method in aqueous conditions was developed. This method enabled the efficient stapling of recombinantly expressed coil-coiled proteins. The resulting stapled protein demonstrated higher stability in its secondary structure than the unstapled version. Furthermore, a thiol–yne coupling was performed by using an a,w-diyne to react with two cysteine residues to synthesize a stapled peptide with two vinyl sulfide groups. The stapled peptide could further react with another biscysteine peptide to yield a bicyclic stapled peptide with enhanced properties. For example, the cell permeability of a stapled peptide was further increased by appending an oligoarginine cell-penetrating peptide. The robustness and versatility of thiol–yne/thiol–ene reactions that can be applied to both synthetic and expressed peptides and proteins were demonstrated.
机译：据报道了硫醇-yne /硫醇-NEE反应合成单 - 和双环杂液肽和蛋白质的应用。首先，开发了在水性条件下基于硫醇基肽的栓塞方法。该方法使具有重组表达的线圈卷曲蛋白的有效装订。得到的填充蛋白在其二级结构中的稳定性高于未列版本。此外，通过使用A，W-Diyne进行硫醇-yne偶联，以与两个半胱氨酸残基反应以合成用两个乙烯基硫化物基团的溺合肽。替代肽可以进一步与另一个烟尾肽反应，以产生具有增强性质的双环浸渍肽。例如，通过附加寡核苷酸细胞穿透肽进一步提高溺爱肽的细胞渗透性。证明了可以应用于合成和表达肽和蛋白质的硫醇-yne /硫醇-NEE反应的鲁棒性和多功能性。

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  • 来源
    《Chemistry: A European journal》 |2017年第29期|共6页
  • 作者

    Yuanxiang Wang; Benjamin J. Bruno; Sean Cornillie; Jason M. Nogieira; Diao Chen; Thomas E. Cheatham III; Carol S. Lim; Danny Hung-Chieh Chou;

  • 作者单位

    Department of Biochemistry University of Utah 15 N Medical Drive East 4100 Salt Lake City UT 84112 (USA);

    Department of Pharmaceutics and Pharmaceutical Chemistry University of Utah 30 S 2000 E Rm 2916 Salt Lake City UT 84112 (USA);

    Department of Medicinal Chemistry University of Utah 30 S 2000 E Rm 4914 Salt Lake City UT 84112 (USA);

    Department of Biochemistry University of Utah 15 N Medical Drive East 4100 Salt Lake City UT 84112 (USA);

    Department of Biochemistry University of Utah 15 N Medical Drive East 4100 Salt Lake City UT 84112 (USA);

    Department of Medicinal Chemistry University of Utah 30 S 2000 E Rm 4914 Salt Lake City UT 84112 (USA);

    Department of Pharmaceutics and Pharmaceutical Chemistry University of Utah 30 S 2000 E Rm 2916 Salt Lake City UT 84112 (USA);

    Department of Biochemistry University of Utah 15 N Medical Drive East 4100 Salt Lake City UT 84112 (USA);

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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

    peptide macrocyclization; peptide stapling; thiol– ene coupling; thiol–yne coupling;

    机译：肽致癌;肽装订;硫醇偶联;硫醇-YNE联轴器;

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