, Volume 47, Issue 3–4, pp 189–196 | Cite as

The use of mobile phase pH and column temperature to reverse the retention order of enantiomers on chiral-AGP®

  • A. Karlsson
  • A. Aspegren


Enantiomeric separation of mosapride and a structurally related compound was performed using chiral chromatography and experimental design. Unique effects of mobile phase pH and column temperature made it possible to control the elution order of the enantiomers when using Chiral-AGP as the solid phase. At a low mobile phase pH (<6) the (R)-enantiomer of mosapride elutes before the (S)-form whereas the (S)-enantiomer elutes first at a high mobile phase pH (>6). By using a mobile phase pH around 6, the column temperature could also be used to control the elution order of the enantiomers of mosapride. Similar effects of mobile phase pH and column temperature were obtained for the enantiomers of a structurally related compound, a metabolite (M1). Isocratic chromatographic systems made it possible to determine enantiomeric impurities less than 0.1% in the respective enantiomer of mosapride. The enantiomers of mosapride as well as the enantiomers of M1 could easily be separated simultaneously using Chiral-AGP and a simple gradient elution.

Key Words

Column liquid chromatography Experimental design Mosapride Reversal of retention order Effect of pH and column temperature 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. [1]
    Chem. Eng. News71 (Sept 27), 38 (1993).Google Scholar
  2. [2]
    S. Allenmark, Protein bonded phases. in A. M. Krstulovic, (Eds) Chiral Separations by HPLC, Ellis Horwood, Chichester, Chapter 11, 1989.Google Scholar
  3. [3]
    J. Hermansson, Trends Anal. Chem.8, 251 (1989).CrossRefGoogle Scholar
  4. [4]
    S. Allenmark, J. Liq. Chromatogr.9, 425 (1986).Google Scholar
  5. [5]
    I. Marle, A. Karlsson, C. Pettersson, J. Chromatogr.604, 185 (1992).CrossRefGoogle Scholar
  6. [6]
    P. Erlandsson, I. Marle, L. Hansson, R. Isaksson, C. Pettersson, G. Pettersson, J. Am. Chem. Soc.112, 4573 (1990).CrossRefGoogle Scholar
  7. [7]
    T. Miwa, T. Miyakawa, M. Kayano, Y. Miyake, J. Chromatogr.408, 316 (1987).CrossRefGoogle Scholar
  8. [8]
    J. Hermansson, M. Eriksson, J. Liq. Chromatogr.9, 621 (1986).Google Scholar
  9. [9]
    G. Schill, I. Wainer, S. Barkan, J. Liq. Chromatogr.9, 164 (1986).Google Scholar
  10. [10]
    A. Karlsson, K. Pettersson, K. Hernqvist, Chirality7, 147 (1995).CrossRefGoogle Scholar
  11. [11]
    T. Morie, S. Kato, H. Harada, N. Yoshida, T. Karasawa, J. Matsumoto, Chem. Pharm. Bull.42, 877 (1994).Google Scholar
  12. [12]
    S. Kato, T. Morie, N. Yoshida, Chem. Pharm. Bull.43, 699 (1995).Google Scholar
  13. [13]
    I. Marle, S. Jönsson, R. Isaksson, C. Pettersson, G. Pettersson, J. Chromatogr.648, 333 (1993).CrossRefGoogle Scholar
  14. [14]
    M. Engquist, J. Hermansson, J. Chromatogr.519, 271 (1990).CrossRefGoogle Scholar
  15. [15]
    J. Iredale, A.-F. Aubry, I. Wainer, Chromatographia31, 329 (1991).CrossRefGoogle Scholar
  16. [16]
    D. Haupt, C. Pettersson, D. Westerlund, J. Biochem. Biophys. Meth.25, 285 (1992).CrossRefGoogle Scholar
  17. [17]
    G. E. P. Box, W. G. Hunter, J. S. Hunter, Statistics for Experimenters. John Wiley & Sons, New York, USA. 1978.Google Scholar
  18. [18]
    P. Geladi, B. R. Kowalski, Anal. Chem. Acta185, 1 (1986).CrossRefGoogle Scholar
  19. [19]
    A. Höskuldsson, J. Chemometrics2, 11 (1988).CrossRefGoogle Scholar
  20. [20]
    S. Wold, Technometrics20, 397 (1978).CrossRefGoogle Scholar
  21. [21]
    I. Fitos, J. Visy, M. Simonyi, J. Hermansson, J. Chromatogr.709, 265 (1995).CrossRefGoogle Scholar
  22. [22]
    I. Yokoyama, Y. Mizuki, T. Yamaguchi, T. Fujii, J. Pharm. Biomed. Anal.,15, 1527 (1997).CrossRefGoogle Scholar
  23. [23]
    K. Balmér, P.-O. Lagerström, B.-A. Persson, G. Schill, J. Chromatogr.592, 331 (1992).CrossRefGoogle Scholar

Copyright information

© Friedr. Vieweg & Sohn Verlagsgesellschaft mbH 1998

Authors and Affiliations

  • A. Karlsson
    • 1
  • A. Aspegren
    • 1
  1. 1.Analytical ChemistryAstra Hässle ABMölndalSweden

Personalised recommendations