具有非芳香性α-Chiral侧链的型均和强聚烯螺旋
Olivier Roy1, Geoffrey Dumonteil1, Sophie Faure1
1Université Clermont Auvergne, CNRS, SIGMA Clermont, Institut de Chimie de Clermont-Ferrand , F-63000 Clermont-Ferrand, France.
Journal of the American Chemical Society
|August 25, 2017
概括
研究人员使用性阻碍的性异形侧链开发了新的类 (模仿) 寡合体. 这些类成功形成全cis聚烯型I (PPI) 螺旋,对于先进的生物材料和药物化学应用至关重要.
科学领域:
- 的化学成分
- 超分子化学
- 材料科学
背景情况:
- 类,N替代的甘氨酸寡合体,是有前途的仿真体.
- 控制脊柱胺基构造是折叠状结构的关键,例如聚烯I型 (PPI) 螺旋.
- 在此之前,芳香侧链在促进cis-amide形态方面表现出成功.
研究的目的:
- 调查固态阻碍的α-合性侧链在形成稳定的状螺旋的潜力.
- 合成和分析带有这些新侧链的类寡合体和混合寡合体.
- 仅使用异形侧链来实现形状均的螺旋.
主要方法:
- 合成 (S) -N- ((1-tert-butylethyl) glycine (Ns1tbe) 的类同类分子.
- 通过X射线结晶学来确定固态结构.
- 用于形状分析的循环二重化 (CD) 光谱.
- 含有 Ns1tbe 和 N-tert-butylglycine (NtBu) 单体的混合基聚体的合成和分析.
主要成果:
- 一个Ns1tbe五合体的X射线晶体结构证实了全cis PPI螺旋.
- Ns1tbe寡合体的CD曲线与PPI螺旋体的曲线相匹配.
- 这是首次报告的CD数据,用于仅具有α-chiral异形侧链的形状均螺旋.
- 一个混合的寡合体,Ac-tBu) 2-s1tbe) 4-tBu) 2-COOtBu,在固态中表现出正规的PPI螺旋,尽管只有50%的奇拉侧链.
结论:
- 性阻碍的α-性侧链可以有效地促进体中全cis PPI螺旋体的形成.
- 这些发现扩大了设计结构控制的体结构的工具包.
- 这些结果为药物化学和生物材料的化物应用开辟了新的途径.
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