Amino acids are natural and versatile building blocks that offer inherent biocompatibility, zwitterionic character, and diverse functional groups, making them attractive for a range of applications. Integrating amino acids into materials can enhance biodegradability and biocompatibility – thus enhancing sustainability – due to their natural origin and also allows one to tailor material properties. However, their rich functionality presents challenges during incorporation, often requiring the use of protecting groups and harsher conditions that undermine green chemistry principles. In this study, we present a straightforward strategy for amino acid incorporation using the aza-Michael reaction with cholinium amino acid ionic liquids (ChAAILs). ChAAILs provide a self-solvating and catalyzing environment, eliminating the need for protecting groups and promoting solvent-free synthesis. A kinetic study of aza-Michael reactions between ChAAILs with various small acrylates demonstrated the range of amino acids that can be incorporated and their product stability. ChAAILs exhibit excellent reactivity not only with simple acrylates, but also hydrophilic polyethers and hydrophobic silicones, offering a promising, generic green approach for amino acid-functional polymer modification.

中文翻译：

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通过氮杂迈克尔反应将氨基酸无保护基团引入聚合物中

氨基酸是天然的多功能构建单元，具有固有的生物相容性、两性离子特征和多样化的官能团，使其对各种应用具有吸引力。由于其天然来源，将氨基酸整合到材料中可以增强生物降解性和生物相容性，从而增强可持续性，并且还可以定制材料特性。然而，它们丰富的功能在掺入过程中提出了挑战，通常需要使用保护基团和破坏绿色化学原则的更恶劣的条件。在这项研究中，我们提出了一种利用氮杂迈克尔反应与胆碱氨基酸离子液体（ChAAIL）进行氨基酸掺入的简单策略。 ChAAIL 提供自溶剂化和催化环境，无需保护基团并促进无溶剂合成。 ChAAIL 与各种小丙烯酸酯之间的 aza-Michael 反应的动力学研究证明了可掺入的氨基酸范围及其产品稳定性。 ChAAIL 不仅与简单的丙烯酸酯表现出优异的反应性，而且还与亲水性聚醚和疏水性有机硅表现出优异的反应性，为氨基酸功能聚合物改性提供了一种有前景的通用绿色方法。