NDLI: Direct High-Performance Liquid Chromatographic Enantiomer Separation of Anti-Inflammatory Planar Chiral [2.2]Paracyclophane-4-acetic Acid

Content Provider	Springer Nature Link
Author	Lämmerhofer, M. Imming, P. Lindner, W.
Copyright Year	2004
Abstract	The development and optimization of an enantioselective HPLC method that allows the baseline separation of the enantiomers of planar chiral [2.2]paracylophane-4-acetic acid (α=1.12; RS=2.6) is reported. The separation is carried out on a chiral anion-exchange type stationary phase based on a tert-butylcarbamoyl quinine selector employing either the reversed-phase or the polar organic mode. A variety of experimental variables have been investigated including organic modifier type and percentage, counter-ion concentration, temperature, and flow rate of the mobile phase. These optimization studies gave insight into mechanistic aspects of the present enantioselective anion-exchangers, which were thoroughly discussed. The optimized method, which was envisaged as a cross-validation study of a previously employed 1H NMR method that made use of a chiral solvating agent, was applied for the enantiomeric excess determination of enantiomeric samples. Thereby, it turned out that the presently employed chromatographic method is better suited for enantiomeric excess determinations, because of its lower limits of quantitation. Samples that were previously assessed to be enantiomerically pure by the 1H NMR technique revealed significant amounts of the enantiomeric impurities by the direct HPLC method (ca. 6–8%).
Starting Page	S13
Ending Page	S17
File Format	PDF
ISSN	00095893
Journal	Chromatographia
Volume Number	60
Issue Number	1
e-ISSN	16121112
Language	English
Publisher	Vieweg Verlag
Publisher Date	2004-02-26
Publisher Place	Wiesbaden
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Column liquid chromatography Enantioselective ion-exchange chromatography Planar chirality tert-Butylcarbamoylquinine [2.2]Paracyclophane derivative
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Analytical Chemistry Biochemistry Clinical Biochemistry

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