Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones,Journal of the American Chemical Society

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Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-03-02 , DOI: 10.1021/jacs.0c13231
Pedro Salas-Ambrosio ₁ , Antoine Tronnet _{2,

3} , Marc Since ₄ , Sandra Bourgeade-Delmas ₅ , Jean-Luc Stigliani ₂ , Amelie Vax ₁ , Sébastien Lecommandoux ₁ , Bruno Dupuy ₃ , Pierre Verhaeghe ₂ , Colin Bonduelle ₁

Affiliation

Cyclic polymers display unique physicochemical and biological properties. However, their development is often limited by their challenging preparation. In this work, we present a simple route to cyclic poly(α-peptoids) from N-alkylated-N-carboxyanhydrides (NNCA) using LiHMDS promoted ring-expansion polymerization (REP) in DMF. This new method allows the unprecedented use of lysine-like monomers in REP to design bioactive macrocycles bearing pharmaceutical potential against Clostridioides difficile, a bacterium responsible for nosocomial infections.

中文翻译：

由双（三甲基甲硅烷基）酰胺锂（LiHMDS）介导的扩环聚合的环状聚（α-拟肽）：生物活性骨架的简单获取

环状聚合物显示出独特的物理化学和生物学特性。然而，他们的发展往往受到他们具有挑战性的准备工作的限制。在这项工作中，我们提出了一种使用 LiHMDS 促进的 DMF 中的扩环聚合（REP）从N-烷基化-N-羧酸酐（NNCA）制备环状聚（α-拟肽）的简单途径。这种新方法允许在 REP 中前所未有地使用赖氨酸样单体来设计具有抗艰难梭菌（一种导致医院感染的细菌）药物潜力的生物活性大环化合物。

更新日期：2021-03-17

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