• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>Chemistry: A European journal >α-Aminoxy Peptoids: A Unique Peptoid Backbone with a Preference for cis-Amide Bonds
【24h】

α-Aminoxy Peptoids: A Unique Peptoid Backbone with a Preference for cis-Amide Bonds

机译：α-氨基氧基拟骨：一种独特的拟肽骨架，优选顺式酰胺键

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

α-Peptoids, or N-substituted glycine oligomers, are an important class of peptidomimetic foldamers with proteolytic stability. Nevertheless, the presence of cis/transamide bond conformers, which contribute to the high flexibility of α-peptoids, is considered as a major drawback. A modified peptoid backbone with an improved control of the amide bond geometry could therefore help to overcome this limitation. Herein, we have performed the first thorough analysis of the folding propensities of α-aminoxy peptoids (or N-substituted 2-aminoxyacetic acid oligomers). To this end, the amide bond geometry and the conformational properties of a series of model α-aminoxy peptoids were investigated by using 1D and 2D NMR experiments, X-ray crystallography, natural bond orbital (NBO) analysis, circular dichroism (CD) spectroscopy, and molecular dynamics (MD) simulations revealing a unique preference for cis-amide bonds even in the absence of cis-directing side chains. The conformational analysis based on the MD simulations revealed that α-aminoxy peptoids can adopt helical conformations that can mimic the spatial arrangement of peptide side chains in a canonical α-helix. Given their ease of synthesis and conformational properties, α-aminoxy peptoids represent a new member of the peptoid family capable of controlling the amide isomerism while maintaining the potential for side-chain diversity.
机译：α-拟肽或N-取代的甘氨酸低聚物，是具有蛋白水解稳定性的重要肽瘤混合物。然而，CIS /烷酰胺键合的存在，其有助于α-拟肽的高柔韧性，被认为是主要的缺点。因此，改进的拟角骨干骨架具有改善的酰胺键几何形状可以有助于克服这种限制。在此，我们已经进行了α-氨基氧基拟拟α-氨基氧基拟肽（或N-取代的2-氨基氧乙酸低聚物）的折叠施力的第一次彻底分析。为此，通过使用1D和2D NMR实验，X射线晶体学，天然键（NBO）分析，圆形二色性（CD）光谱研究了通过使用1D和2D NMR实验研究了一系列α-氨基氧基拟α-氨基氧基拟α-氨基氧基拟拟α-氨基氧基肽的构象性质并且，即使在没有顺式引导侧链的情况下，也揭示了即使在没有顺应引导侧链的情况下为顺式酰胺键的独特偏好。基于MD模拟的构象分析表明，α-氨基氧基拟骨膜可以采用螺旋构象，其可以模拟肽侧链在规范α-螺旋中的空间排列。鉴于它们易于合成和构象性质，α-氨基氧基拟肽代表能够控制酰胺异构的拟肽家族的新成员，同时保持侧链多样性的潜力。

著录项

  • 来源
    《Chemistry: A European journal》 |2017年第15期|共9页
  • 作者

    Viktoria Krieger; Emanuele Ciglia; Roland Thoma; Vera Vasylyeva; Benedikt Frieg; Nader de Sousa Amadeu; Thomas Kurz; Christoph Janiak; Holger Gohlke; Finn K. Hansen;

  • 作者单位

    Institute of Pharmaceutical and Medicinal Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Pharmaceutical and Medicinal Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Inorganic and Structural Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Inorganic and Structural Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Pharmaceutical and Medicinal Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Inorganic and Structural Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Pharmaceutical and Medicinal Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Inorganic and Structural Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Pharmaceutical and Medicinal Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

    Institute of Pharmaceutical and Medicinal Chemistry Heinrich-Heine-Universit?t Düsseldorf Universit?tsstrasse 1 40225 Düsseldorf (Germany);

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

    aminoxy peptoids; conformational analysis; foldamers; peptidomimetics; peptoids;

    机译：氨基氧基拟肽;构象分析;糊涂虫;肽瘤;拟肽;

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号