氨基酸基聚电解质的一锅法合成及纳米粒子合成,Biomacromolecules

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氨基酸基聚电解质的一锅法合成及纳米粒子合成
Biomacromolecules ( IF 5.5 ) Pub Date : 2016-12-02 00:00:00 , DOI: 10.1021/acs.biomac.6b01420
Stefan Mommer ₁ , Helmut Keul ₁ , Martin Möller ₁

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在该手稿中，具有环氧基和通过氨基甲酸酯键连接的硫代内酯环的双环单体用于合成氨基酸官能的聚电解质。在第一步中，氨基酸的锂盐通过开环，形成酰胺键和硫醇基团与硫代内酯环选择性地反应。在第二步骤中，在碱的存在下，通过将硫醇盐加成到环氧化物上而形成聚合物结构单元。该反应在室温下在水中作为溶剂发生。所得的聚合物结构单元具有带有羟基和氨基酸侧基的聚（硫醚氨基甲酸酯）主链；氨基酸与主链的连接通过酰胺键发生。作为概念证明，使用了一系列选定的氨基酸及其衍生物：甘氨酸，丙氨酸，酪氨酸，谷氨酸，ε-氨基己酸（作为赖氨酸替代物），BOC-赖氨酸-O-甲酯，BOC-赖氨酸和二肽肌肽。所得的聚合物结构单元的分子量为M _n = 1830–9590 g / mol完全基于生物基成分和可生物降解成分。示例性地，使用甘氨酸和赖氨酸甲酯的锂盐，获得了阴离子和阳离子聚电解质构件。两种聚电解质溶液的混合物导致形成聚电解质复合物（PEC）。随着聚电解质溶液浓度的降低，PEC的半径减小。

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One-Pot Synthesis of Amino Acid-Based Polyelectrolytes and Nanoparticle Synthesis

In this manuscript, a biscyclic monomer with an epoxide and a thiolactone ring connected by a urethane bond is used for the synthesis of amino acid-functional polyelectrolytes. In a first step, lithium salts of amino acids react selectively with the thiolactone ring by ring-opening, formation of an amide bond, and a thiol group. In a second step and in the presence of a base a polymeric building block is formed by polyaddition of the thiolate to the epoxide ring. The reaction occurs at room temperature in water as solvent. The resulting polymeric building block has a poly(thioether urethane) backbone, with hydroxyl- and amino acid side groups; the connection of the amino acid to the backbone occurs by an amide bond. As proof of concept, a selected series of amino acids and derivatives of such is used: glycine, alanine, tyrosine, glutamic acid, ε-amino caproic acid (as a lysine surrogate), BOC-lysine-O-methyl ester, BOC-lysine, and the dipeptide carnosine. The resulting polymer building blocks with molecular weights of M_n = 1830–9590 g/mol are entirely based on both bio-based and biodegradable components. Exemplarily, using the lithium salts of glycine and lysine methyl ester, anionic and cationic polyelectrolyte building blocks are obtained. A mixture of the two polyelectrolyte solutions results in the formation of polyelectrolyte complexes (PECs). With decreasing concentration of the polyelectrolyte solutions, the radii of PECs decrease.

更新日期：2016-12-02

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