苯丙氨酸衍生物分子印迹聚合物的制备及手性识别机理

Preparation and Chiral Recognition of N-Tert-Butoxycarbonyl-L-Phenylalanine Imprinted Polymer

以L-特丁氧羰基苯丙氨酸(Boc-L-Phe)为模板分子,甲基丙烯酸(MAA)为功能单体,乙二醇二甲基丙烯酸酯(EDMA)为交联剂,合成了一种新型的分子印迹聚合物(MIP),将其作为色谱固定相,对其对映异构体进行手性拆分。分别采用红外光谱和核磁共振氢谱系统研究了印迹聚合物的结合位点和识别机理。结果表明,该聚合物通过协同氢键作用形成1∶3型配合物,专一地结合Boc-L-Phe分子。MAA分子羧基上的C=O是氢键的质子接受体;Boc-L-Phe分子上的氨基以及羧基上的氢氧键是质子的给予体,是与MAA形成氢键作用的选择性识别位点。

The molecularly imprinted polymers（ MIPs） for N-tert-butoxycarbonyl-L-phenylalanine（ Boc-L-Phe）were prepared by photo polymerization using Boc-L-Phe as template,methylacrylic acid（ MAA） as functional monomer,and ethlene glycol dimethacrylate（ EDMA） as crosslinker. The enantiomeric recognition performance of these MIPs in the high performance liquid chromatography（ HPLC） mode was investigated. Infrared spectroscopy and1H-NMR spectroscopy were used to detect the binding sites and the recognition mechanism of MIPs. The results show that the template Boc-L-Phe and functional monomers form 1∶ 3 complexes before polymerization,and the interaction between MAA and Boc-L-Phe is relied on hydrogen bond. The C = O of MAA is the hydrogen bond acceptor. The amino and hydroxyl groups of Boc-L-Phe are the hydrogen bond donor. These are the binding sits between template molecule and functional monomer.