Yan Jie, Marina Paula Facal, Blencowe Anton
Applied Chemistry and Translational Biomaterials (ACTB) Group, Clinical and Health Sciences, University of South Australia, Adelaide, SA 5001, Australia.
Polymers (Basel). 2021 Apr 26;13(9):1403. doi: 10.3390/polym13091403.
Amino end-group functionalised polyglycols are important intermediates in the synthesis of sophisticated polymeric architectures and biomaterials. Herein, we report a facile strategy for the end-group conversion of hydroxyl-terminated polyglycols to amino-terminated polyglycols in high isolated yields and with excellent end-group fidelity. Following traditional conversion of polyglycol hydroxyl end-groups to azides via the corresponding mesylate, reduction with zinc in the presence of ammonium chloride afforded a range of amino end-group functionalised poly(ethylene glycol) and poly(propylene glycol) homopolymers and copolymers with isolated yields of 82-99% and end-group conversions of >99% as determined by NMR spectroscopy and MALDI ToF MS. Furthermore, this process is applicable to a sequential reagent addition approach without intermediate polymer isolation steps with only a slight reduction in yield and end-group conversion (95%). Importantly, a simple work-up procedure provides access to high purity polyglycols without contamination from other reagents.
氨基端基功能化聚二醇是合成复杂聚合物结构和生物材料的重要中间体。在此，我们报道了一种简便的策略，可将羟基封端的聚二醇高产率且高保真地转化为氨基封端的聚二醇。通过相应的甲磺酸酯将聚二醇羟基端基传统转化为叠氮化物后，在氯化铵存在下用锌还原，得到了一系列氨基端基功能化的聚（乙二醇）和聚（丙二醇）均聚物及共聚物，通过核磁共振光谱和基质辅助激光解吸电离飞行时间质谱测定，其分离产率为82 - 99%，端基转化率>99%。此外，该方法适用于连续添加试剂的方法，无需中间聚合物分离步骤，产率和端基转化率仅略有降低（95%）。重要的是，一个简单的后处理程序可得到无其他试剂污染的高纯度聚二醇。
