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Molecular Modeling of Enantioseparation of Phenylazetidin Derivatives by Cyclodextrins

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Abstract

β-Lactams are one of the most widely used types of antibiotics. As β-lactams are chiral, the enantiomeric separation of these compounds was investigated using cyclodextrins, frequently used as chiral separators. Molecular modeling methods were utilized in order to predict possible enantioseparation of four model compounds. Our results revealed that permethylated β-cyclodextrin is more likely to chirally separate the phenylazetidin derivates than the parent β-cyclodextrin. LC experiments using cyclodextrin as chiral stationary phase in most cases confirmed our prediction; however, more experiments and statistical evaluation of the results are needed in order to judge the prediction power of the molecular dynamic method.

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Acknowledgment

The financial supports of Jedlik Ányos grant 00180/2007, NKFP_07_A3_NATURSEP and OTKA K 67563 are acknowledged.

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Authors and Affiliations

  1. Virtua Drug, Ltd, Csalogany st. 4C, 1015, Budapest, Hungary

    Zsolt Bikádi, István Hazai & Eszter Hazai

  2. Department of Inorganic and Analytical Chemistry, University of Szeged, 6720, Szeged, Hungary

    Gábor Fodor & Antal Péter

  3. Delta Informatika, Szentendrei út 39-53, Budapest, 1033, Hungary

    Péter Hári

  4. CycloLab Cyclodextrin Research and Development Laboratory Ltd., P.O. Box 435, 1525, Budapest, Hungary

    Julianna Szemán & Lajos Szente

  5. Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös 6, 6720, Szeged, Hungary

    Ferenc Fülöp

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  1. Zsolt Bikádi
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  2. Gábor Fodor
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  9. Eszter Hazai
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Correspondence to Eszter Hazai.

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Bikádi, Z., Fodor, G., Hazai, I. et al. Molecular Modeling of Enantioseparation of Phenylazetidin Derivatives by Cyclodextrins. Chroma 71 (Suppl 1), 21–28 (2010). https://doi.org/10.1365/s10337-009-1461-9

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  • DOI: https://doi.org/10.1365/s10337-009-1461-9

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