Enantioseparation of Chiral Sulfoxides on Amylose-Based Columns: Comparison of Normal Phase Liquid Chromatography and Supercritical Fluid Chromatography
- 328 Downloads
We present enantioseparation of a series of racemic sulfoxides on three different amylose-based polysaccharide columns. Two of them have the amylose units modified with dimethylphenyl carbamoyl groups (Chiralpak AD-H and Chiralpak IA), while the third one possesses a carbamoyl moiety with an additional chiral centre (Chiralpak AS-H). The enantioseparation of selected analytes was achieved in high-performance liquid chromatography (HPLC) and the full analyte set was enantiomerically resolved using supercritical fluid chromatography (SFC). Comparing the results obtained in both modes, we show that enantioseparation under SFC conditions is superior to HPLC mode in terms of speed, while retaining excellent enantioselectivity and resolution. Faster elution of analytes was observed on increasing the polarity of the co-solvent (modifier) in the mobile phase. This trend is apparent in both chromatographic modes. Documenting the important role of the additional chiral centre, Chiralpak AS-H provided the best chromatographic parameters resulting in the enantioseparation of all analytes.
KeywordsEnantioseparation Sulfoxides Polysaccharide chiral stationary phases Amylose Supercritical fluid chromatography Liquid chromatography
Compliance with Ethical Standards
The work was supported by Czech Science Foundation (Grant number 16-17689Y).
This article does not contain any studies with human participants or animals performed by any of the authors.
Conflict of interest
The authors declare that they have no conflict of interest.
- 1.Liu Y, Gu X-H (2011) Pharmacology of chiral drugs. In: Chiral drugs. Wiley, New York, pp. 323–345Google Scholar
- 2.Geditz MCK, Lindner W, Lämmerhofer M, Heinkele G, Kerb R, Ramharter M, Schwab M, Hofmann U (2014) Simultaneous quantification of mefloquine (+)- and (−)-enantiomers and the carboxy metabolite in dried blood spots by liquid chromatography/tandem mass spectrometry. J Chromatogr B 968:32–39CrossRefGoogle Scholar
- 8.Holakovský R, März M, Cibulka R (2015) Urea derivatives based on a 1,1′-binaphthalene skeleton as chiral solvating agents for sulfoxides. Tetrahedron: Asymm 26:1328–1334Google Scholar
- 15.Meričko D, Lehotay J, Čižmárik J (2008) Enantioseparation of chiral sulfoxides using teicoplanine chiral stationary phases and kinetic study of decomposition in human plasma. Pharmazie 63:854–859Google Scholar
- 17.Gegenava M, Chankvetadze L, Farkas T, Chankvetadze B (2014) Enantioseparation of selected chiral sulfoxides in high-performance liquid chromatography with polysaccharide-based chiral selectors in polar organic mobile phases with emphasis on enantiomer elution order. J Sep Sci 37:1083–1088CrossRefGoogle Scholar
- 42.Mahut M, Lindner W, Lämmerhofer M, Gargano A, Zhang T, Franco P (2012) Enantiomer and topoisomer separation of acidic compounds on anion-exchanger chiral stationary phases by HPLC and SFC. LCGC Europe 25:11Google Scholar