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手性液相色谱在对映体绝对构型测定中的贡献。

Chiral liquid chromatography contribution to the determination of the absolute configuration of enantiomers.

作者信息

Roussel Christian, Del Rio Alberto, Pierrot-Sanders Johanna, Piras Patrick, Vanthuyne Nicolas

机构信息

Faculté des Sciences St. Jêrôme, UMR Chirotechnologies: Catalyse et Biocatalyse, Université Aix-Marseille III, Avenue Escadrille Normandie Niemen, F-13397 Marseille Cedex 20, France.

出版信息

J Chromatogr A. 2004 May 28;1037(1-2):311-28. doi: 10.1016/j.chroma.2004.01.065.

DOI:10.1016/j.chroma.2004.01.065
PMID:15214673
Abstract

The review covers examples in which chiral HPLC, as a source of pure enantiomers, has been combined with classical methods (X-ray, vibrational circular dichroism (VCD), enzymatic resolutions, nuclear magnetic resonance (NMR) techniques, optical rotation, circular dichroism (CD)) for the on- or off-line determination of absolute configuration of enantiomers. Furthermore, it is outlined that chiral HPLC, which associates enantioseparation process and classical purification process, opens new perspectives in the classical determination of absolute configuration by chemical correlation or chemical interconversion methods. The review also contains a discussion about the various approaches to predict the absolute configuration from the retention behavior of the enantiomers on chiral stationary phases (CSPs). Some examples illustrate the advantages and limitations of molecular modeling methods and the use of chiral recognition models. The assumptions underlying some of these methods are critically analyzed and some possible emerging new strategies are outlined.

摘要

该综述涵盖了一些实例,其中手性高效液相色谱作为纯对映体的来源,已与经典方法(X射线、振动圆二色性(VCD)、酶法拆分、核磁共振(NMR)技术、旋光、圆二色性(CD))相结合,用于对映体绝对构型的在线或离线测定。此外,还概述了将对映体分离过程与经典纯化过程相结合的手性高效液相色谱,为通过化学关联或化学互变方法进行经典绝对构型测定开辟了新的前景。该综述还讨论了从对映体在手性固定相(CSP)上的保留行为预测绝对构型的各种方法。一些实例说明了分子建模方法的优点和局限性以及手性识别模型的应用。对其中一些方法所依据的假设进行了批判性分析,并概述了一些可能出现的新策略。

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