含有拥挤的tert-丁侧链的类寡合体的固相合成
Zacharie Bordas1, Sophie Faure1, Olivier Roy1
1Université Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, 63000 Clermont-Ferrand, France.
The Journal of organic chemistry
|March 10, 2025
概括
我们开发了一种修改后的亚单体协议,用于N-tert-butyl-glycine (NtBu) 类的固相合成. 这种方法克服了固态障碍,使得能够产生含有NtBu的类寡合体和复杂结构.
科学领域:
- 类和类模拟化学 和类模拟化学
- 聚合物合成的方法
- 有机化学 有机化学
背景情况:
- N-tert-butyl-glycine (NtBu) 是一种类单体,已知可诱导特定的二次结构.
- 甲基-丁基组的固体质量大多有利于cis-amide键的几何结构,促进转和螺旋.
- 之前,含有NtBu的类的固体相合成受到硬质挑战的阻碍.
研究的目的:
- 报道了第一个成功的固体相合成含有NtBu的peptoids.
- 开发和优化一个修改的亚单体协议,以结合NtBu单体.
- 用各种具有挑战性的peptoid序列来证明该协议的有效性.
主要方法:
- 使用修改后的亚单体协议进行固相合成.
- 通过添加基或基本树脂预处理,优化了DIC介导的化步骤.
- 使用酸代替酸,并包括酸预激活步骤.
主要成果:
- 成功合成了含有NtBu的同类聚合物,长度高达12mer.
- 证明了该协议适用于合成具有高度拥挤的侧链的类.
- 确定了成功的乙化和改进合成功效的关键修改.
结论:
- 修改后的亚单体协议使含有NtBu的类的高效固体相合成成为可能.
- 这种进步允许构建以前无法访问的复杂的peptoid结构.
- 该协议为探索基于peptoid的材料和治疗方法开辟了新的途径.
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