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LC Enantioseparation of β-Lactam Stereoisomers through the Use of β-Cyclodextrin-Based Chiral Stationary Phases

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Abstract

Direct liquid chromatographic methods were developed to investigate the enantioseparation of 19 β-lactams on three cyclodextrin-bonded chiral stationary phases: permethyl-β-cyclodextrin, β-cyclodextrin and R,S-hydroxypropyl-β-cyclodextrin, prepared by a novel synthetic route. 17 of the 19 β-lactam stereoisomers were partially or baseline-separated on at least one of the tested chiral stationary phases. The influence of the structures of the β-lactams (the positions and types of the substituents, the size of the attached rings) on the enantiomer separation is discussed. The permethylated β-cyclodextrin selector proved to be the most effective one for the tested analytes.

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Acknowledgments

The authors are grateful to Ms. Zs. Zachár and Ms. O. Nemes for their valuable technical assistance. This work was supported financially by the grants Jedlik Ányos 00180/2007, NKFP_07_A3_NATURSEP and OTKA 67563.

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Authors and Affiliations

  1. Department of Inorganic and Analytical Chemistry, University of Szeged, 6720, Szeged Dóm tér 7, Hungary

    Gábor Fodor, István Ilisz & Antal Péter

  2. CycloLab R&D Ltd, Budapest, 1097, Illatos út 7, Hungary

    Julianna Szemán, Róbert Iványi & Lajos Szente

  3. ChiroQuest Chiral Technologies Development Ltd, Budapest, 1075, Rumbach, Hungary

    Gábor Varga

  4. Institute of Pharmaceutical Chemistry, University of Szeged, Szeged, Hungary

    Enikő Forró & Ferenc Fülöp

Authors
  1. Gábor Fodor
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  2. István Ilisz
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  3. Julianna Szemán
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  4. Róbert Iványi
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  5. Lajos Szente
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  6. Gábor Varga
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  7. Enikő Forró
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  8. Ferenc Fülöp
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  9. Antal Péter
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Corresponding author

Correspondence to István Ilisz.

Additional information

Presented at: 8th Balaton Symposium on High-Performance Separation Methods, Siofok, Hungary, September 2–4, 2009.

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Fodor, G., Ilisz, I., Szemán, J. et al. LC Enantioseparation of β-Lactam Stereoisomers through the Use of β-Cyclodextrin-Based Chiral Stationary Phases. Chroma 71 (Suppl 1), 29–34 (2010). https://doi.org/10.1365/s10337-010-1514-0

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  • DOI: https://doi.org/10.1365/s10337-010-1514-0

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