Functional poly(amino acid)s such as poly(ε-lysine) have many potential high-value applications. However, the effective chemosynthetic strategy for these materials remains a big challenge in polymer chemistry; the key issue is how to design and protect amino groups for the effective ring-opening polymerization (ROP). Our lab succeeded in chemosynthesis of poly(ε-lysine) via delicate design of a 2,5-dimethylpyrrole protecting group and metal-catalyzed ROP processes, but harsh reaction conditions (e.g., ca. 260 °C) were required. Herein, we developed a superbase t-BuP₄-catalyzed ROP of ε-lactam derivatives, affording high molecular weight poly(ε-lysine) bearing pendant protected amino groups with high monomer conversion (up to 95%). The organocatalytic polymerization could proceed at low reaction temperature (e.g., 60 °C) compatible with readily removable protecting groups, providing a sustainable and new methodology toward facile preparation of poly(ε-lysine).

中文翻译：

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轻度条件下简便的有机催化合成聚（ε-赖氨酸）

功能性聚氨基酸（例如聚ε-赖氨酸）具有许多潜在的高价值应用。然而，对于这些材料而言，有效的化学合成策略仍然是高分子化学中的一大挑战。关键问题是如何设计和保护氨基以进行有效的开环聚合（ROP）。我们的实验室通过精心设计的2,5-二甲基吡咯保护基和金属催化的ROP工艺成功地化学合成了聚（ε-赖氨酸），但需要苛刻的反应条件（例如，约260°C）。在这里，我们开发了一个超级碱基t -BuP ₄催化的ε-内酰胺衍生物的ROP，可得到带有侧链保护的氨基的高分子量聚（ε-赖氨酸），且单体转化率高（高达95％）。有机催化聚合反应可在与易于除去的保护基团相容的低反应温度（例如60°C）下进行，从而为简便地制备聚（ε-赖氨酸）提供了一种可持续的新方法。