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Enantioseparation of Novel Amino Analogs of Indole Phytoalexins on Macrocyclic Glycopeptide-Based Chiral Stationary Phase

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Abstract

Direct chiral separation of the enantiomers of spirobrassinin, 1-methoxyspirobrassinin and ten novel cis- and trans-diastereoisomers of 2-amino analogs of indole phytoalexin 1-methoxyspirobrassinol methyl ether on macrocyclic glycopeptide-based chiral stationary phase (CSP) with teicoplanin (Chirobiotic T) was studied. Normal phase eluents containing n-hexane with modifiers ethanol and 2-propanol were used. The effects of mobile phase composition, structure of the analytes and temperature were investigated. Chiral resolution on teicoplanin CSP was achieved only in the case of trans-diastereoisomers. The van’t Hoff plots were found to show linear behavior in all cases. It was found that studied normal phase enantioseparations were enthalpy driven. The elution order of the enantiomers was determined in some cases.

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Acknowledgments

The authors (TG and JP) are grateful to the Hermes LabSystems for the technical support of this work. This work was supported by the Slovak Research and Development Agency under the contract No. APVV-0514-06.

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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

    Tat’ána Gondová, Ján Petrovaj & Martin Fabián

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

    Peter Kutschy, Zuzana Čurillová & Aneta Salayová

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

    Daniel W. Armstrong

Authors
  1. Tat’ána Gondová
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  2. Ján Petrovaj
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  3. Peter Kutschy
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  4. Zuzana Čurillová
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  5. Aneta Salayová
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  6. Martin Fabián
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  7. Daniel W. Armstrong
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Correspondence to Tat’ána Gondová.

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Gondová, T., Petrovaj, J., Kutschy, P. et al. Enantioseparation of Novel Amino Analogs of Indole Phytoalexins on Macrocyclic Glycopeptide-Based Chiral Stationary Phase. Chromatographia 74, 751–757 (2011). https://doi.org/10.1007/s10337-011-2143-y

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  • DOI: https://doi.org/10.1007/s10337-011-2143-y

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