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HPLC Enantioseparation of Novel Spirobrassinin Analogs on the Cyclofructan Chiral Stationary Phases

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Abstract

A novel series of nine chiral analogs of spirobrassinin, which have potential biological activity, was separated for the first time on three different derivatized cyclofructan chiral stationary phases in the normal phase mode. The effects of mobile phase composition, the type and concentration of polar modifier, additives, and the analyte structure on the retention and enantioseparation were studied. The results proved that for cyclofructan-based chiral stationary phases, the R-naphthylethyl carbamate cyclofructan 6 provides the best separation efficiency for the analyzed compounds. The effect of temperature on the separation was also investigated and the corresponding thermodynamic parameters were evaluated from linear Van’t Hoff plots (lnk or lnα versus 1/T). It was found that the enantioseparation was enthalpy controlled. In addition, the elution order of the enantiomers was determined in all the cases.

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Acknowledgements

The authors gratefully acknowledge the financial support received from the Scientific Grant Agency VEGA of Slovak Republic (Grant No. 1/0253/16).

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Authors and Affiliations

  1. Department of Analytical Chemistry, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic

    Marianna Moskaľová, Oleksandr Kozlov & Taťána Gondová

  2. Department of Organic Chemistry, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovak Republic

    Mariana Budovská

  3. Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX, 76019, USA

    Daniel W. Armstrong

Authors
  1. Marianna Moskaľová
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  2. Oleksandr Kozlov
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  3. Taťána Gondová
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  4. Mariana Budovská
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  5. Daniel W. Armstrong
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Correspondence to Taťána Gondová.

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Moskaľová, M., Kozlov, O., Gondová, T. et al. HPLC Enantioseparation of Novel Spirobrassinin Analogs on the Cyclofructan Chiral Stationary Phases. Chromatographia 80, 53–62 (2017). https://doi.org/10.1007/s10337-016-3212-z

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  • DOI: https://doi.org/10.1007/s10337-016-3212-z

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