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首页> 外文期刊>Chemistry: A European journal >Helically Chiral Peptides That Contain Ferrocene-1,1'-diamine Scaffolds as a Turn Inducer
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Helically Chiral Peptides That Contain Ferrocene-1,1'-diamine Scaffolds as a Turn Inducer

机译：螺旋手性肽，其含有二茂铁-1,1'-二胺支架作为转动诱导剂

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摘要

A series of peptides that contain homo-and heterochiral Ala-Pro sequences attached to the turn-inducing ferrocene-1,1'-diamine scaffold were synthesized. The effects of the backbone chirality and the N-terminal group (Boc/Ac) on the conformational properties of the novel peptidomimetics were thoroughly explored by IR, NMR, and CD spectroscopy and the experimental observations were corroborated by DFT studies in solution. The most stable conformers of the homochiral peptides adopted the interstrand hydrogen-bond patterns, realized through ten-and thirteen-membered rings. The common feature of the most stable conformers of the heterochiral peptides was the adoption of the turn-like structures that feature the simultaneous intra-(seven-membered) and interstrand (sixteen-membered) hydrogen-bonded rings. An exchange of two N-terminal groups had a somewhat larger influence on the distribution of the hydrogen-bond patterns in homochiral than in heterochiral derivatives. The homochiral peptides that contain pyridine moieties as metal coordination sites formed 1:1 complexes with divalent metal ions, which included Zn~(2+), Cd~(2+), Cu~(2+) and Fe~(2+).
机译：合成了一系列含有环状与诱导的二茂铁-1'-二胺支架上的同源和异质ALA-Pro序列的肽。通过IR，NMR和CD光谱彻底探索了骨干手术和N-末端组（BOC / AC）对新型肽模拟物的构象性能的影响，并通过DFT研究在溶液中证实了实验观察。冠制肽的最稳定的蜂胶状物采用了穿过十个和十三元环的替代氢键图案。杂种肽最稳定的蜂胶状物的常见特征是采用具有同时（七元）和interstrand（16-元）的氢键环的转向结构。对两种N-末端基团的交换对同性化合物中的氢键模式的分布产生的影响略大，而不是异细衍生物。含有吡啶部分作为金属配位位点的蛋白编密集肽，其具有二价金属离子的1：1络合物，其包括Zn〜（2+），Cd〜（2+），Cu〜（2+）和Fe〜（2+） 。

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  • 来源
    《Chemistry: A European journal》 |2017年第43期|共24页
  • 作者

    Monika Kova?evi?; Ivan Kodrin; Sun?ica Roca; Kre?imir Mol?anov; Yuning Shen; Bimalendu Adhikari; Heinz-Bernhard Kraatz; Lidija Bari?i?;

  • 作者单位

    Department of Chemistry and Biochemistry Faculty of Food Technology and Biotechnology University of Zagreb Pierottijeva 6 Zagreb (Croatia);

    Department of Chemistry Faculty of Science University of Zagreb Horvatovac 102a Zagreb (Croatia);

    NMR Centre Rudēr Bo?kovi? Institute Bijeni?ka cesta 54 Zagreb (Croatia);

    Division of Physical Chemistry Rudēr Bo?kovi? Institute Bijeni?ka cesta 54 Zagreb (Croatia);

    Department of Physical and Environmental Sciences University of Toronto 1265 Military Trail Toronto M1C 1 A4 (Canada);

    Department of Chemical Sciences Indian Institute of Science Education and Research (IISER) Mohali Knowledge City Sector 81 S. A. S. Nagar Manauli PO Punjab 140306 (India);

    Department of Physical and Environmental Sciences University of Toronto 1265 Military Trail Toronto M1C 1 A4 (Canada);

    Department of Chemistry and Biochemistry Faculty of Food Technology and Biotechnology University of Zagreb Pierottijeva 6 Zagreb (Croatia);

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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

    chirality; conformation analysis; density functional calculations; ferrocene; peptidomietics;

    机译：手性;构象分析;密度函数计算;亚茂铁;肽;

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