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首页> 外文期刊>Journal of chromatography, A: Including electrophoresis and other separation methods >Chromatographic and spectroscopic studies on the chiral recognition of sulfated beta-cyclodextrin as chiral mobile phase additive Enantiomeric separation of a chiral amine
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Chromatographic and spectroscopic studies on the chiral recognition of sulfated beta-cyclodextrin as chiral mobile phase additive Enantiomeric separation of a chiral amine

机译：手性识别硫酸化β-环糊精作为手性流动相添加剂的色谱和光谱研究手性胺的对映体分离

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摘要

A fast enantiomeric separation of a chiral aromatic amine was achieved, using ultra high pressure liquid chromatography and highly sulfated beta-cyclodextrin (S-beta-CD) as a chiral additive in the mobile phase. The stationary phase consisted of a core-shell support with a particle size of 2.7 pm. Under these conditions the base-line separation was obtained within 2.5 min. The influence of the concentration of the additive, along with the thermodynamics of the separation, was studied. Vibrational circular dichroism (VCD) spectroscopy was applied to assess the absolute configuration of the two enantiomeric analytes, as well as the interaction of these enantiomers with the S-beta-CD. The VCD results revealed that S-beta-CD undergoes a temperature-induced conformational change. Further, VCD experiments indicate that the interactions of the two enantiomers with the S-beta-CD occur through an inclusion of the aromatic part of the analyte, as well as through electrostatic interaction between the protonated amine and the sulfate groups located at the narrow part of the S-beta-CD. Molecular mechanics calculations performed according to the VCD results are consistent with experimental data, providing further evidence of these interactions. (c) 2008 Elsevier B.V. All rights reserved.
机译：使用超高压液相色谱和在流动相中作为手性添加剂使用高度硫酸化的β-环糊精（S-β-CD），实现了手性芳族胺的快速对映异构体分离。固定相由粒径为2.7 pm的核壳载体组成。在这些条件下，可以在2.5分钟内获得基线分离。研究了添加剂浓度的影响以及分离的热力学。振动圆二色性（VCD）光谱用于评估两种对映体分析物的绝对构型，以及这些对映体与S-β-CD的相互作用。 VCD结果表明S-beta-CD经历了温度诱导的构象变化。此外，VCD实验表明，两种对映体与S-β-CD的相互作用是通过包含分析物的芳族部分以及质子化胺与位于狭窄部分的硫酸根之间的静电相互作用而发生的。 S-beta-CD。根据VCD结果进行的分子力学计算与实验数据一致，为这些相互作用提供了进一步的证据。 （c）2008 Elsevier B.V.保留所有权利。

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