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化学学报
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化学学报 ›› 2003, Vol. 61 ›› Issue (11): 1885-1889. 上一篇    

研究论文

以混旋邻氯扁桃酸为模板的分子印迹聚合物的制备及拆分性能研究

李萍;胡濬喆;林保平;戎非;袁春伟   

  1. 东南大学生物医学工程系;东南大学化学化工系
  • 发布日期:2003-11-15

Preparation of Molecularly Imprinted Polymer with Racemic 2- Chloromandelic Acid and Study on Its Chiral Resolution

Li Ping;Hu Junze;Ling Baoping;Rong Fei;Yuan Chunwei   

  1. Key Laboratory of Molecular and Biomolecular Electronics, Department of Biomedical Engineering, Southeast University;Department of Chemistry and Chemical Engineering, Southeast University
  • Published:2003-11-15

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556

被引次数

43 | 5

以混旋邻氯扁桃酸为模板分子和合成的(S)-(1-萘乙基)-丙烯酰胺为手性功能 单体制备分子印迹聚合物作为色谱固定相，对混旋邻氯扁桃酸有较好的拆分能力， 分离因子α达到1.36。但对模板分子的类似物混旋扁桃酸和对氯扁桃酸没有拆分能 力。用Hyperchem软件模拟了(S)-邻氯扁桃酸与(S)-(1-萘乙基)-丙烯酰胺形成的复 合物的结构模型，其在聚合物母体中留下的具有立体构型和作用力双重识别的S-S 型空穴，对(S)-邻氯扁桃酸有较强的保留作用，从而达到对混旋物拆分的目的。

关键词: 分子印迹聚合物, 邻氯扁桃酸, 色谱, 固定相, 丙烯酰胺

The molecularly imprinted polymer was prepared by racemic 2- chloromandelic acid as template and synthesized (S)-acryloyl-l- naphthylethylamine as chiral functional monomer. The molecularly imprinted polymers as stationaiy phase had good chiral resolution ability to 2-chloromandelic acid enantiomers and the separation factor a was calculated as 1.36. But this polymer showed no resolution to the analogues of the template, such as racemic 4-chloromandelic acid and mandelic acid. The structure of (S)-2-chloromandelic acid interacting with (S)-acryloy-l-naphthylethylamine was simulated by Hyperchem software. The S-S type of cavities left by imprinting in polymer matrix showed double recognition of spatial configuration and binding interaction and had stronger retention capability to (S)-2- chloromandelic acid, so as to get the good enantioseperation.

Key words: molecularly imprinted polymer, 2-chloromandelic acid, CHROMATOGRAPHY, STATIONARY PHASE, PROPENAMIDE

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