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纤维素2,3-位和2,3,6-位苯基氨基甲酸酯手性固定相的选择性研究

Study on Enantioselectivity of Celluloses Derived by Phenylcarbamate at 2,3or 2,3,6-Positions

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【作者】 常银霞周玲玲袁黎明

【Author】 CHANG Yinxia1,2,ZHOU Lingling1,YUAN Liming1(1.Faculty of Chemistry and Chemical Engineering,Yunnan Normal University,Kunming 650092,China;2.College of Chemistry and Material Science,Shanxi Normal University,Linfen 041000,China)

【机构】 云南师范大学化学化工学院云南师范大学化学化工学院 云南昆明650092山西师范大学化学与材料科学学院山西临汾041000云南昆明650092

【摘要】 合成了纤维素-2,3,6-三苯基氨基甲酸酯、纤维素-2,3-二苯基氨基甲酸酯、纤维素-2,3,6-三(3,5-二甲基苯基氨基甲酸酯)和纤维素-2,3-二(3,5-二甲基苯基氨基甲酸酯)4种纤维素衍生物手性固定相,用正己烷-异丙醇(体积比为9∶1)混合液作流动相,对9种手性化合物进行了高效液相色谱拆分。实验结果表明:对所测的9个样品,纤维素-2,3-二苯基氨基甲酸酯的手性选择性大大好于纤维素-2,3,6-三苯基氨基甲酸酯;而纤维素-2,3-二(3,5-二甲基苯基氨基甲酸酯)与纤维素-2,3,6-三(3,5-二甲基苯基氨基甲酸酯)的分离因子针对不同的对映体各有优点,但前者通常具有更小的保留因子,可以缩短一定的分析时间。

【Abstract】 Cellulose-2,3,6-trisphenylcarbamate,cellulose-2,3-bisphenylcarbamate,cellulose-2,3,6-tris(3,5-dimethylphenylcarbamate) and cellulose-2,3-bis(3,5-dimethylphenylcarbamate) were synthesized and respectively coated on silica gel as chiral stationary phases for high performance liquid chromatography(HPLC).Nine pairs of enantiomers,which are(±)-phenyl-1,2-ethanediol,(±)2-phenyl-1-propanol,DL-alpha-methylbenzylamine,DL-mandelic acid,(±)-1-(1-naphthyl) ethanol,(±)-propranolol,(±)-3-benzyloxy-1,2-propanediol,DL-tyrosine and(±)-di-O,O-p-toluyl-D-tartaric acid,were separated using hexane-isopropanol as mobile phase on the columns packed with the chiral stationary phases.For comparative reasons,the ratio of hexane/isopropanol in the eluent was kept at 9∶1(v/v) in all experiments,and the chromatographic separations were performed at 30 ℃ with a flow rate of 0.5 mL/min.All the test solutes were detected at 254 nm.The results showed that enantioseparation of cellulose-2,3-bisphenylcarbamate was better than cellulose-2,3,6-trisphenylcarbamate for the test enantiomers,and cellulose-2,3-bis(3,5dimethylphenylcarbamate) had low retention factors and short analysis times for most enantiomers and good separation factors for some racemates compared to cellulose-2,3,6-tris(3,5-dimethylphenylcarbamate).

【基金】 国家自然科学基金(No.30160092);高等学校青年教师教学科研奖励计划(No.2001298);云南省自然科学基金(No.2005E0006Z)资助项目
  • 【文献出处】 色谱 ,Chinese Journal of Chromatography , 编辑部邮箱 ,2007年02期
  • 【分类号】O657.7
  • 【被引频次】10
  • 【下载频次】278
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