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Two Synthetic Methods for Preparation of Chiral Stationary Phases Using Crystalline Degradation Products of Vancomycin: Column Performance for Enantioseparation of Acidic and Basic Drugs

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Abstract

Two chiral stationary phases (CSPs) based on crystalline degradation products (CDPs) of vancomycin by using different synthetic methods were prepared and compared. Crystalline degradation products of vancomycin were produced by hydrolytic loss of ammonia from vancomycin molecules. Performances of two chiral columns prepared with these degradation products were investigated using several acidic and basic drugs as model analytes. Retention and resolution of these analytes on the prepared columns, as two main parameters, in enantioseparation were studied. The results demonstrated that the stationary phase preparation procedure has a significant effect on the column performance. The resolving powers of prepared columns for enantiomers resolution were changed with the variation in vancomycin-CDP coverage on the silica support. Elemental analysis was used to monitor the surface coverage of silica support by vancomycin-CDP. The results showed that both columns can be successfully applied to chiral separation studies.

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Acknowledgments

The support of this work by the Research Council of Tarbiat Modares University and Iran National Science Foundation (INSF) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Tarbiat Modares University, Tehran, Iran

    Assem Abdollahpour

  2. Razi Herbal Medicines Research Center, Lorestan University of Medical Sciences, PO Box 68149-89468, Khorramabad, Iran

    Rouhollah Heydari

  3. Department of Chemistry, Razi University, Kermanshah, Iran

    Mojtaba Shamsipur

Authors
  1. Assem Abdollahpour
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  2. Rouhollah Heydari
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  3. Mojtaba Shamsipur
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Correspondence to Rouhollah Heydari or Mojtaba Shamsipur.

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Abdollahpour, A., Heydari, R. & Shamsipur, M. Two Synthetic Methods for Preparation of Chiral Stationary Phases Using Crystalline Degradation Products of Vancomycin: Column Performance for Enantioseparation of Acidic and Basic Drugs. AAPS PharmSciTech 18, 1855–1862 (2017). https://doi.org/10.1208/s12249-016-0660-6

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  • DOI: https://doi.org/10.1208/s12249-016-0660-6

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