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Enantioseparation of Chiral Sulfoxides on Amylose-Based Columns: Comparison of Normal Phase Liquid Chromatography and Supercritical Fluid Chromatography

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Abstract

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.

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Authors and Affiliations

  1. Forensic Laboratory of Biologically Active Substances, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic

    Natalie Kolderová & Martin Kuchař

  2. Department of Organic Chemistry, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic

    Tomáš Neveselý, Jiří Šturala, Roman Holakovský & Michal Kohout

  3. Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic

    Martin Kuchař

Authors
  1. Natalie Kolderová
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  2. Tomáš Neveselý
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  3. Jiří Šturala
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  4. Martin Kuchař
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  5. Roman Holakovský
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  6. Michal Kohout
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Corresponding author

Correspondence to Michal Kohout.

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The work was supported by Czech Science Foundation (Grant number 16-17689Y).

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This article does not contain any studies with human participants or animals performed by any of the authors.

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The authors declare that they have no conflict of interest.

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Published in the topical collection Advances in Chromatography and Electrophoresis & Chiranal 2016 with guest editor Jan Petr.

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Kolderová, N., Neveselý, T., Šturala, J. et al. Enantioseparation of Chiral Sulfoxides on Amylose-Based Columns: Comparison of Normal Phase Liquid Chromatography and Supercritical Fluid Chromatography. Chromatographia 80, 547–557 (2017). https://doi.org/10.1007/s10337-016-3234-6

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  • DOI: https://doi.org/10.1007/s10337-016-3234-6

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