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Chiral separation on achiral stationary phases with different functionalities using β-cyclodextrin in the mobile phase and application to bioanalysis and coupled columns

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Summary

β-cyclodextrin was used in the mobile phase as chiral selector for separating the enantiomers of terbutaline, chlorthalidone and oxazepam. The effect on chiral resolution using e.g. hydrophobic, polar or cation exchanging stationary phases was investigated. Both the chiral separation factor and retention level were affected by the concentration of methanol and β-cyclodextrin. The stationary phase had no effect on the chiral separation only on the level of retention. By tuning the concentration of β-cyclodextrin and methanol in the mobile phase chiral separation could be obtained on most stationary phases. By changing the stationary phase while adjusting the mobile phase composition to maintain the chiral selectivity, improvements of the selectivity towards e.g. endogenous compounds can be obtained when separating enantiomers in complex matrixes as biological fluids. Further improvement on selectivity can be obtained if coupled columns are used. This is examplified for separation of chlorthalidone and terbutaline enantiomers in biological fluids by coupling an achiral column to another achiral column and using a mobile phase containing β-cyclodextrin on the last column.

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References

  1. E.J. Ariens, Eur. J. Clin. Pharmacol.26, 663 (1984).

    Google Scholar 

  2. K. Williams, E. Lee, Drugs30, 333 (1985).

    Google Scholar 

  3. W. Lindner, C. Pettersson, in “Liquid Chromatography in Pharmaceutical Development”,I. Wainer, ed., Aster, Springfield, OR, 1986, p. 63.

    Google Scholar 

  4. R. Däppen, H. Arm, V. Meyer, J. Chromatogr.373, 1 (1986).

    Google Scholar 

  5. I. Wainer, M.C. Alembik, “Chromatographic Chiral Separations”,M. Zief, L.J. Crane, ed., Marcel Dekker Inc., New York, 1988, p. 355.

    Google Scholar 

  6. L.-E. Edholm, C. Lindberg, J. Paulson, A. Walhagen, J. Chromatogr.424, 61 (1988).

    Google Scholar 

  7. A. Walhagen, L.-E. Edholm, B.-M. Kennedy, L.C. Xiao, Chirality1, 20 (1989).

    Google Scholar 

  8. A. Walhagen, L.-E. Edholm, J. Chromatogr.473, 371 (1989).

    Google Scholar 

  9. A. Walhagen, L.-E. Edholm, C.E.M. Heeremans, R.A.M. Van der Hoeven, W.M.A. Niessen, U.R. Tjaden, J. van der Greef, J. Chromatogr.474, 257 (1989).

    Google Scholar 

  10. D.W. Armstrong, T.J. Ward, R.D. Armstrong, T.E. Beesley, Science232, 1132 (1986).

    Google Scholar 

  11. J. Szejtli, “Cyclodextrins and their inclusion complexes”, Akadémiai Kiadó, Budapest, 1982, p. 95.

    Google Scholar 

  12. D. Sybilska, J. Zukowski, J. Bojarski, J. Liq. Chromatogr.9, 591 (1986).

    Google Scholar 

  13. M. Gazdag, G. Szepesi, L. Huszár, J. Chromatogr.351, 128 (1986).

    Google Scholar 

  14. A.E. Fell, T.A.G. Noctor, J.E. Mama, B.J. Clark, J. Chromatogr.434, 377 (1988).

    Google Scholar 

  15. K. Cabrera, G. Schwinn, Kontakte (Darmstadt)3, 3 (1989).

    Google Scholar 

  16. G. Geisslinger, K. Dietzel, D. Loew, O. Schuster, G. Rau, G. Lachmann, K. Brune, J. Chromatogr.491, 139 (1989).

    Google Scholar 

  17. M.H. Huang Chandler, R.J. Guttendorf, R.A. Blouin, P.J. Wedlund, J. Chromatogr.419, 426 (1987).

    Google Scholar 

  18. J. Zukowski, D. Sybilska, J. Bojarski, J. Chromatogr.364, 225 (1986).

    Google Scholar 

  19. A.M. Stalcup, S.-C. Chang, D. Amstrong, J. Pitha, J. Chromatogr.513, 181 (1990).

    Google Scholar 

  20. D. Armstrong, A.M. Stalcup, M.L. Hilton, J.D. Duncan, J.R. Faulkner, Jr., S.-C. Chang, Anal. Chem.62, 1610 (1990).

    Google Scholar 

  21. V. Schurig, H.-P. Nowotny, J. Chromatogr.441, 155 (1988).

    Google Scholar 

  22. W.A. König, S. Lutz, P. Miscnick-Lübbecke, B. Brassat, G. Wenz, J. Chromatogr.447, 193 (1988).

    Google Scholar 

  23. D. Armstrong, W. Li, J. Pitha, Anal. Chem.62, 214 (1990).

    Google Scholar 

  24. L.R. Snyder, J.J. Kirkland, “Introduction to Modern Liquid Chromatography”, Wiley, New York, 2nd edition, 1979, p. 34.

    Google Scholar 

  25. S.T. Balke, “Quantitative Column Liquid Chromatography a servey of chemometric methods”, Journal of Chromatography Library-volume 29, Elsevier, 1984, p. 77.

  26. Y. Aso, S. Yoshioka, T. Shibazaki, M. Uchiyama, Chem. Pharm. Bull.36, 1834 (1988).

    Google Scholar 

  27. S.K. Yang, X.-L. Lu, J. Pharmaceutical Sciences78, 789 (1989).

    Google Scholar 

  28. D.C. Muirhead, R.B. Christie, J. Chromatogr.416, 420 (1987).

    Google Scholar 

  29. S.-E. Jacobsson, S. Jönsson, C. Lindberg, L.-Å. Svensson, Biomed. Mass. Spectrom.7, 265 (1980).

    Google Scholar 

  30. H.L.J. Fleuren, C.A.M. van Ginneken, J.M. van Rossum, J. Pharm. Sci.68, 1056 (1979).

    Google Scholar 

  31. J. Barrett, W. Franklin Smyth, I.E. Davidson, J. Pharm. Pharmac.25, 387 (1972).

    Google Scholar 

  32. K. Fujimura, T. Ueda, M. Kitagawa, H. Takayanagi, T. Ando, Anal. Chem.58, 2668 (1986).

    Google Scholar 

  33. L.J.C. Love, M. Arunyanart, A.C.S. Symp. Ser.297, 226 (1986).

    Google Scholar 

  34. M. Gazdag, G. Szepesi, L. Huszár, J. Chromatogr.371, 227 (1986).

    Google Scholar 

  35. D.Y. Pharr, Z.S. Fu, T.K. Smith, WL. Hinze, Anal. Chem.61, 275 (1989).

    Google Scholar 

  36. Y.-Q. Chu, I.W. Wainer, Pharm. Res.5, 680 (1988).

    Google Scholar 

  37. I.W. Wainer, R.M. Stiffin, J. Chromatogr.424, 158 (1988).

    Google Scholar 

  38. Y.-Q. Chu, I.W. Wainer, J. Chromatogr.497, 191 (1989).

    Google Scholar 

  39. A. Rizzi, J. Chromatogr.513, 195 (1990).

    Google Scholar 

  40. F. Gimenez, R. Farinotti, A. Thuillier, G. Hazebroucq, I.W. Wainer, J. Chromatogr.529, 339 (1990).

    Google Scholar 

  41. L. Silan, P. Jadaud, L.R. Whitfield, I.W. Wainer, J. Chromatogr.532, 227 (1990).

    Google Scholar 

  42. J.F.K. Huber, R. van der Linden, E. Ecker, M. Oreans, J. Chromatogr.83, 267 (1973).

    Google Scholar 

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Authors and Affiliations

  1. Technical Analytical Chemistry, University of Lund, P.O. Box 124, S-221 00, Lund, Sweden

    A. Walhagen

  2. Bioanalytical Chemistry, AB Draco (Subsidiary of AB Astra), P.O. Box 34, S-221 00, Lund, Sweden

    L. -E. Edholm

Authors
  1. A. Walhagen
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  2. L. -E. Edholm
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Walhagen, A., Edholm, L.E. Chiral separation on achiral stationary phases with different functionalities using β-cyclodextrin in the mobile phase and application to bioanalysis and coupled columns. Chromatographia 32, 215–223 (1991). https://doi.org/10.1007/BF02276243

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  • DOI: https://doi.org/10.1007/BF02276243

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