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逆流色谱法拆分对映体。以L-脯氨酸衍生物作为手性选择剂的优化及缺点。

Enantiomer separation by counter-current chromatography. Optimisation and drawbacks in the use of L-proline derivatives as chiral selectors.

作者信息

Delgado Beatriz, Pérez Eva, Santano M Carmen, Minguillón Cristina

机构信息

Institut de Recerca Biomèdica, Parc Científic de Barcelona, Josep Samitier 1-5, E-08028 Barcelona, Spain.

出版信息

J Chromatogr A. 2005 Oct 21;1092(1):36-42. doi: 10.1016/j.chroma.2005.03.034. Epub 2005 Apr 2.

DOI:10.1016/j.chroma.2005.03.034
PMID:16188558
Abstract

Several L-proline and (4R)-hydroxy-L-proline derivatives were evaluated as chiral selectors (CSs) in the separation of enantiomers by counter-current chromatography (CCC). A variety of biphasic solvent systems, all of organic/aqueous nature, were tested in order to determine the appropriate distribution for CSs and racemates (N-(3,5-dinitrobenzoyl)-(+/-)-leucine and (+/-)-ketoprofen). Successful separations of DNB-(+/-)-leucine in analogous experimental conditions allow the comparative study of the enantioselectivity displayed by the considered CSs. The low solubility of certain CSs limits their applicability for preparative purposes even for improved enantioselectivity. The effect that the nature and pH of the buffer solutions used as a component of the solvent system have on the separation was also studied.

摘要

评估了几种L-脯氨酸和(4R)-羟基-L-脯氨酸衍生物作为手性选择剂(CSs),用于通过逆流色谱法(CCC)分离对映体。测试了各种均为有机/水性质的双相溶剂系统,以确定CSs和外消旋体(N-(3,5-二硝基苯甲酰基)-(±)-亮氨酸和(±)-酮洛芬)的合适分配。在类似实验条件下成功分离DNB-(±)-亮氨酸,使得能够对所考虑的CSs表现出的对映选择性进行比较研究。某些CSs的低溶解度限制了它们在制备目的中的适用性,即使其对映选择性有所提高。还研究了用作溶剂系统组分的缓冲溶液的性质和pH对分离的影响。

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引用本文的文献

1
Separation of alpha-cyclohexylmandelic acid enantiomers using biphasic chiral recognition high-speed counter-current chromatography.用双相手性识别高速逆流色谱法分离α-环己基扁桃酸对映体。
J Chromatogr A. 2010 Apr 30;1217(18):3044-52. doi: 10.1016/j.chroma.2010.02.077. Epub 2010 Mar 4.