Retention of fluorinated chiral selectors in biphasic fluorinated solvent systems and its application to the separation of enantiomers by countercurrent chromatography
Retention of fluorinated chiral selectors in biphasic fluorinated solvent systems and its application to the separation of enantiomers by countercurrent chromatography
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DOI：
10.1016/j.chroma.2009.09.071
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发表时间：
2010-02-12
影响因子：
4.1
通讯作者：
Minguillon, Cristina
中科院分区：
文献类型：
--
作者：
Maria Perez, Anna;Minguillon, Cristina
乙氧基壬基丁烷（ENFB）已被用作新的两相溶剂混合物的组分。对几种混合物作为逆流色谱溶剂系统的适用性进行了试验。评价了ENFB/2-PrOH/H2O混合物与氟化手性选择剂（CS）组合分离对映体的适用性。N-全氟十一酰基-L-脯氨酸-3，5-二甲基苯胺（2）。类似于先前使用的N-十二烷基-L-脯氨酸-3，5-二甲基苯胺（1）。为此目的而合成。新的溶剂系统的能力，以保留氟化CS作为固定在氟化相使用进行了检查。出于比较目的，在类似条件下应用手性选择剂I。此外，MTBE/磷酸盐缓冲液溶剂系统也与两种CS一起使用。结果表明，ENFB/2-PrOH/H_2O（25：35：40）体系对DNB-Leu和DNB-Leu-tBu具有良好的拆分效果。在氟化溶剂系统中保持对映选择性而不影响洗脱时间。实现了DNB-Leu-tBu的完全分离，并且未检测到CS泄漏到移动的相中。(C)2009爱思唯尔有限公司版权所有。
Ethoxynonafluorobutane (ENFB) has been used as a component of new biphasic solvent mixtures. The suitability of several mixtures as solvent systems in countercurrent chromatography was tested. The applicability of the ENFB/2-PrOH/H2O mixture to the separation of enantiomers, in combination with a fluorinated chiral selector (CS), was evaluated. N-Perfluoroundecanoyl-L-proline-3,5-dimethylanilide (2). analogous to the previously used N-dodecyl-L-proline-3,5-dimethylanilide (1). was synthesized for this purpose. The capacity of the new solvent system to retain the fluorinated CS in the fluorinated phase used as stationary was examined. Chiral selector I was applied in analogous conditions for comparative purposes. Additionally, MTBE/phosphate buffer solvent system was also used with the two CSs. The ENFB/2-PrOH/H2O (25:35:40) mixture was found to be adequate in the enantioseparation of DNB-Leu and DNB-Leu-tBu. Enantioselectivity was maintained in the fluorinated solvent system without compromising eluting time. The complete separation of DNB-Leu-tBu was achieved and no leaks of CS to the mobile phase were detected. (C) 2009 Elsevier B.V. All rights reserved.