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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (9): 1102-1106. 上一篇    下一篇

研究论文

具有乙二醇侧链的聚谷氨酸酯的合成、表征及其两亲性

徐旭，伍国琳*，张洁，王亦农，范云鸽，马建标   

  1. (南开大学高分子化学研究所 功能高分子材料重点实验室 天津 300071)
  • 投稿日期:2007-09-13 修回日期:2007-11-06 发布日期:2008-05-14
  • 通讯作者: 伍国琳

Synthesis and Amphiphilic Property of Ethyleneglycol Functionalized Polyglutamate

XU Xu WU Guo-Lin* ZHANG Jie WANG Yi-Nong FAN Yun-Ge MA Jian-Biao   

  1. (Key Laboratory of Functional Polymer Materials (Ministry of Education), Institute of Polymer Chemistry, Nankai University, Tianjin 300071)
  • Received:2007-09-13 Revised:2007-11-06 Published:2008-05-14
  • Contact: WU Guolin

PDF

1344

被引次数

24

聚氨基酸具有良好的生物相容性和规整二级结构, 可作为生物医学材料应用. 如果聚氨基酸具有两亲性, 则能够形成纳米尺寸的胶束结构, 有望作为生物降解药物释放载体. 为得到两亲性的聚谷氨酸, 通过小分子开环聚合的方法直接制备了具有乙二醇侧链的聚谷氨酸酯. 首先制备了γ-(2-(甲氧基)乙基)-L-谷氨酸酯和γ-(2-(2-甲氧基乙氧基)乙基)-L-谷氨酸酯, 然后与三聚光气反应得到其N-羧酸酐(NCA). N-羧酸酐(NCA)单体经开环聚合反应合成了具有乙二醇侧链的聚谷氨酸酯(PEGnG). 利用IR, 1H NMR, GPC和吸湿性测定等方法对所合成聚合物进行了详细的表征. 结果表明随着侧链中EG含量的提高, 聚L-谷氨酸酯的亲水性有明显改善. 透射电镜的结果表明, 聚谷氨酸二乙二醇单甲醚酯(PEG2G)在水溶液中能够形成稳定胶束结构.

关键词: 聚氨基酸, 谷氨酸酯, 开环聚合, 胶束

Mono- and diethyleneglycol functionalized polyglutamates (PEGnG) were synthesized by the ring-opening polymerization of N-carboxyanhydride (NCA) directly. Firstly, EG-L-glutamates were synthesized by the reaction of glutamic acid and ethylene glycol monomethyl ether or di(ethylene glycol) monomethyl ether. And then, EG-L-glutamate-N-carboxyanhydride was prepared by glutamate and triphosgen. The structure and basic properties were characterized by IR, 1H NMR, GPC and water affinity measurements. The results showed that the hydrophilicity was increased effectively, which depends on the number of EG groups on the side chain. Poly[α-2-(2-methoxyethoxy)-ethyl-γ-glutamate] (PEG2G) was found to be water soluble. The TEM result showed that PEG2G self-assembled into micelles in water.

Key words: poly(amino acid), glutamate, ring-opening polymerization, micelle