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芳香醇异构体在纤维素-三（3,5二-甲基苯基氨基甲酸酯）色谱柱上的手性分离

吴旭日, 范宇, 陈依军

吴旭日, 范宇, 陈依军. 芳香醇异构体在纤维素-三（3,5二-甲基苯基氨基甲酸酯）色谱柱上的手性分离[J]. 中国药科大学学报, 2014, 45(2): 213-220. DOI: 10.11665/j.issn.1000-5048.20140215
引用本文: 吴旭日, 范宇, 陈依军. 芳香醇异构体在纤维素-三（3,5二-甲基苯基氨基甲酸酯）色谱柱上的手性分离[J]. 中国药科大学学报, 2014, 45(2): 213-220. DOI: 10.11665/j.issn.1000-5048.20140215
shu
WU Xuri, FAN Yu, CHEN Yijun. Chromatographic separation of aryl alcohol enantiomers by cellulose tris(3, 5-dimethylphenylcarbamate)-based column[J]. Journal of China Pharmaceutical University, 2014, 45(2): 213-220. DOI: 10.11665/j.issn.1000-5048.20140215
Citation: WU Xuri, FAN Yu, CHEN Yijun. Chromatographic separation of aryl alcohol enantiomers by cellulose tris(3, 5-dimethylphenylcarbamate)-based column[J]. Journal of China Pharmaceutical University, 2014, 45(2): 213-220. DOI: 10.11665/j.issn.1000-5048.20140215
shu

芳香醇异构体在纤维素-三（3,5二-甲基苯基氨基甲酸酯）色谱柱上的手性分离

Chromatographic separation of aryl alcohol enantiomers by cellulose tris(3, 5-dimethylphenylcarbamate)-based column

摘要

    摘要
  • 摘要: 手性化合物的构型测定一般难度较大。本文在利用涂布纤维素-三(3，5-二甲基苯基氨基甲酸酯)(CDMPC)手性固定相的反相色谱柱Chiralcel OD-RH分析芳香醇异构体的过程中发现，芳香醇异构体的立体构型与其在手性柱上的色谱行为即洗脱顺序存在着内在关联。为排除立体构型与洗脱顺序可能出现的错误关联，本文借助热力学、IR和NMR等手段对CDMPC和芳香醇异构体之间的相互作用进行了系统的研究，阐明了CDMPC手性空穴中的功能基团C=O，NH与芳香醇异构体形成的氢键是异构体得以分离并呈现出特定洗脱顺序的决定因素。因此，基于化合物在Chiralcel OD-RH柱上的色谱行为预测立体构型将有可能成为一种初步确定芳香醇系列异构体立体化学构型的快速简便方法。
    Abstract: The determination of absolute configuration of chiral compounds is typically a prerequisite for various investigations. In the present study, a Chiralcel OD-RH column coated with cellulose tris(3, 5-dimethylphenylcarbamate)(CDMPC)was used to evaluate the capability of enantiomeric separation of chiral aryl alcohols with a reversed phase HPLC. Results showed that the chromatographic behaviors, in terms of elution order, were closely correlated with absolute configurations of the chiral aryl alcohols. Therefore, this simple HPLC method can serve as an alternative approach to facilitate the determination of absolute configurations of chiral aryl alcohols according to their elution orders. To rule out the possibility of false assignments, the underlying mechanism of this chromatographic behavior was further studied by IR and NMR. Hydrogen bondings between C=O, NH in the chiral cavity of CDMPC and different enantiomers were the key factor for the respective recognition and elution orders.
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  • 刊出日期:  2014-04-24

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