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Solvent-generated HPLC systems with β-cyclodextrin derivatives as chiral additives

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Abstract

It is shown that enantioselective solvent-generated liquid-liquid and liquid-solid Chromatographic systems with β-cyclodextrin derivatives can be realized. The liquid-liquid systems are based on ternary solvent systems of limited miscibility, containing chiral additives; the chiral stationary phase is spontaneously generated on the porous microparticulate silica used as a solid support. In the solvent-generated adsorption systems a very small proportion of β-cyclodextrin derivatives is added to the mobile phase. These components act as column activators, since they are strongly adsorbed on the RP solid support where they form new stereoselective adsorption sites. It is demonstrated that dynamically generated systems with β-cyclodextrin derivatives as chiral agents are powerful and versatile tools for enantioseparation of different types of compounds. This technique creates not only a new type of selectivity but also leads to very stable and reproducible Chromatographic columns.

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References

  1. J. F. K. Huber,16th Intern. Symp. Chromatog., Paris, 1986.

  2. J. F. K. Huber, M. Pawłowska, P. Markl,Chromatographia 1984,17, 653.

    Google Scholar 

  3. J. F. K. Huber, M. Pawłowska, P. Markl,Chromatographia 1984,19, 19.

    Google Scholar 

  4. J. F. K. Huber, M. Pawłowska, P. Markl,J. Chromatog. 1990,500, 257.

    Google Scholar 

  5. P. J. Crombeen, S. Heemstra, J. C. Kraak,J. Liq. Chromatog. 1980,3, 1151.

    Google Scholar 

  6. R. M. McCormick, B. L. Karger,J. Chromatog. 1980,199, 259.

    Google Scholar 

  7. P. Markl,Chromatographia 1981,14, 355.

    Google Scholar 

  8. P. Daucik, A. M. Rizzi, J. F. K. Huber,J. Chromatog. 1988,442, 53.

    Google Scholar 

  9. S. H. Hansen, P. Helboe, U. Lund,J. Chromatog. 1983,270, 77.

    Google Scholar 

  10. P. Helboe, S. H. Hansen, M. Thomsen, in:Advances in Chromatography, Vol. 28 (J. C. Giddings, E. Grushka, P. R. Brown, eds.), Dekker, New York, 1989, p. 195.

    Google Scholar 

  11. C. Pettersson, H. W. Stuurman,J. Chromatog. Sci. 1981,22, 441.

    Google Scholar 

  12. W. F. Lindner, J. Hirschboeck,J. Liq. Chromatog. 1986,9, 551.

    Google Scholar 

  13. A. Shibukawa, T. Nakagawa, in:Chiral Separation by HPLC (A. M. Krstulovic, ed.), Horwood, Chichester, 1989, p. 476.

    Google Scholar 

  14. J. Zukowski, D. Sybilska, J. Bojarski,J. Chromatog. 1983,364, 225.

    Google Scholar 

  15. J. Zukowski, D. Sybilska, J. Bojarski, J. Szejtli,J. Chromatog. 1988,436, 381.

    Google Scholar 

  16. J. Zukowski, R. Nowakowski,J. Liq. Chromatog. 1989,9, 1545.

    Google Scholar 

  17. M. Pawłowska, J. Lipkowski,J. Chromatog. (submitted for publication).

  18. W. S. McClenahan, E. B. Tilden, C. S. Hudson,J. Am. Chem. Soc. 1942,64, 2143.

    Google Scholar 

  19. A. I. Vogel,Textbook of Practical Organic Chemistry, Longmans, London, 1978.

    Google Scholar 

  20. J. F. K. Huber, C. A. M. Meijers, J. A. R. J. Hulsman,Anal. Chem. 1972,44, 111.

    PubMed  Google Scholar 

  21. A. I. Vorob'eva, M. Kh. Karapet'yants,Zh. Fiz. Khim. 1986,40, 3018.

    Google Scholar 

  22. C. A. Meijers, J. A. R. J. Hulsman, J. F. K. Huber,Fresenius' Z. Anal. Chem. 1972,261, 347.

    Google Scholar 

  23. K. Harata, K. Uekama, M. Otagiri, F. Hirayama,J. Incl. Phenom. 1984,1, 279.

    Google Scholar 

  24. V. Schurig, H.-P. Nowotny,J. Chromatog. 1988,441, 155.

    Google Scholar 

  25. T. J. Ward, D. W. Armstrong,J. Liq. Chromatog. 1986,9, 407.

    Google Scholar 

  26. J. Szejtli,Cyclodextrin Technology, Kluwer, Dordrecht, 1988, p. 51.

    Google Scholar 

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Dedicated to Professor J. F. K. Huber on the occasion of his 65th birthday

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Pawłowska, M., Zukowski, J. Solvent-generated HPLC systems with β-cyclodextrin derivatives as chiral additives. Mikrochim Acta 102, 55–69 (1990). https://doi.org/10.1007/BF01244288

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  • DOI: https://doi.org/10.1007/BF01244288

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