Chirality pp 180-204 | Cite as

Strategies for Liquid Chromatographic Resolution of Enantiomers



Classic liquid-liquid chromatographic separation relies basically on the distribution of a compound between two immiscible phases by which one is moving (the mobile phase) with respect to the stationary phase. However, in the same way, similar processes occur in the chromatography by classifying the stationary phase as adsorbent which might be a chemically modified surface (e.g. with chiral compounds). The chemical and physico-chemical nature of the phases may vary to a great extent and leads to the various modes of chromatography together with their technical translation. The heart of every chromatographic system is the column which contains the (modified) particles whose surface serves as stationary phase and where the separation of a mixture of compounds (in the following for instance a mixture of stereoisomers or enantiomers) depending on the mobile phase chosen takes place. During the passage of the compounds through the packed column (over the stationary phase) the formation of chromatographic bonds with a concentration profile according to a Gaussian distribution curve takes place, and when the individual sorption isotherms of each component are non-identical, the compounds will become separated. This is the idealistic case, further details on chromatography may be found in more specific textbooks.


Crown Ether Chiral Selector Chiral Stationary Phase Chiral Recognition Amino Acid Amide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Ogsten AG (1948) Nature 162: 963CrossRefGoogle Scholar
  2. 2.
    Dalgliesh C (1952) J Chem Soc 3940Google Scholar
  3. 3.
    Pirkle W, Pochapsky T (1986) J Chromatogr 369: 175CrossRefGoogle Scholar
  4. 4.
    Ruach-Puntigam S, Erni F, Lindner W (1990) J Chromatogr, paper submittedGoogle Scholar
  5. 5.
    Burkle W, Karfunkel H, Schurig V (1984) J Chromatogr 288: 1CrossRefGoogle Scholar
  6. 6.
    Pirkle W, Pochapsky T (1989) Chem Rev 89: 347–362CrossRefGoogle Scholar
  7. 7.
    Lindner W (1987) Chromatographia 24: 97–107CrossRefGoogle Scholar
  8. 8.
    Däppen R, Arm H, Meyer V (1986) H Chromatogr 373: 1CrossRefGoogle Scholar
  9. 9.
    Lindner W, Pettersson C (1985) In: Wainer J (ed) Liquid chromatography in pharmaceutical Developments: An introduction. Springfield, p 62Google Scholar
  10. 10.
    Schurig V (1983) In: Morrsion J (ed) Asymmetric Synthesis, vol 1, Analytical Methods. Academic, New YorkGoogle Scholar
  11. 11.
    Pirkle W, Finn J (1983) In: Morrison J (ed) Asymmetric Synthesis, vol 1, Analytical Methods. Academic, New YorkGoogle Scholar
  12. 12.
    Allenmark S (1988) In: Chromatographic Enantioseparation: Methods and Applications. Ellis Horwood John Wiley, New YorkGoogle Scholar
  13. 13.
    Krstulovic A (1989) In: Chiral Separation by HPCL. Ellis Horwood John Wiley, New YorkGoogle Scholar
  14. 14.
    Lough W (1989) In: Chiral liquid chromatography. Blackie, Chapman and Hall, New YorkGoogle Scholar
  15. 15.
    Davankov V, Navratil J, Walton H (1988) In: Ligand Exchange Chromatography. CRC Press Inc, Boca Raton Florida USAGoogle Scholar
  16. 16.
    Dent C (1948) Biochem J 43: 169CrossRefGoogle Scholar
  17. 17.
    Dalgliesh C (1952) Biochem J 52: 3CrossRefGoogle Scholar
  18. 18.
    Contractor S, Wragg J (1965) Nature 208: 71CrossRefGoogle Scholar
  19. 19.
    Hesse G, Hagel R (1973) Chromatographia 6: 277CrossRefGoogle Scholar
  20. 20.
    Shibata T, Okamoto Y, Ishii K (1986) J Liq Chromatogr 9: 313CrossRefGoogle Scholar
  21. 21.
    Mannschreck A, Kolber H, Wernicke R (1985) Kontakte (E Merck Darmstadt FRG) 40. and citations thereinGoogle Scholar
  22. 22.
    Werner A (1989) Kontakte (E Merck Darmstadt FRG) 50Google Scholar
  23. 23.
    Okamoto Y, Kawashima M, Hatada K (1984) J Am Chem Soc 106: 5357CrossRefGoogle Scholar
  24. 24.
    Application Guide for chiral column selection. Daicel Chemical Industries (1989)Google Scholar
  25. 25.
    Ariens E (1984) Eur J Clin Pharmacol 26: 663CrossRefGoogle Scholar
  26. 26.
    Stewart K, Doherty R (1973) Proc Natl. Acad Sci USA 70: 2850CrossRefGoogle Scholar
  27. 27.
    Allenmark S, Bomgren B (1982) J Chromatogr 252: 297CrossRefGoogle Scholar
  28. 28.
    Hermansson J (1983) J Chromatogr 269: 71CrossRefGoogle Scholar
  29. 29.
    Schill G, Wainer I, Barkan S (1986) J Chromatogr 265: 73CrossRefGoogle Scholar
  30. Schill G, Wainer I, Barkan S (1986) J Liq Chromatogr 9: 641CrossRefGoogle Scholar
  31. 30a.
    Hermansson J, Schill G (1988) In: Brown PA, Hartwick R (eds) High Performance Liquid Chromatography. Wiley, New YorkGoogle Scholar
  32. 30b.
    Erlandsson P, Marie J, Hansson L, Isaksson R, Pettersson C, Pettersson G (1990) J Am Chem Soc 112: 4573CrossRefGoogle Scholar
  33. 31.
    Blaschke G (1974) Chem Ber 107: 237CrossRefGoogle Scholar
  34. 32.
    Blaschke G, Frankel W, Kinkel J (1987) Kontakte (E Merck Darmstadt FRG) 3Google Scholar
  35. 33.
    Okamoto Y, Hatada K (1986) L Liq Chromatogr 9: 369 and citations thereinGoogle Scholar
  36. 34.
    Ward T, Armstrong D (1986) J Liq Chromatogr 9: 407CrossRefGoogle Scholar
  37. 35.
    Iingenfelter D, Helgeson R, Cram C (1981) J Org Chem 46: 393CrossRefGoogle Scholar
  38. 36.
    Armstrong D, Stalcup A, Hilton M, Duncan J, Faulkner J Jr., Chang S-H (1990) Anal Chem 62: 1610CrossRefGoogle Scholar
  39. 37.
    Lindner W, Hirschböck I (1984) J Pharmac a Biol Anal 2 (2): 183CrossRefGoogle Scholar
  40. 38.
    Dobashi A, Hara S (1987) J Org Chem 52: 2490CrossRefGoogle Scholar
  41. 39.
    Prelog V, Mutak S, Kovacevic K (1983) Helv Chim Acta 66: 2279CrossRefGoogle Scholar
  42. 40.
    Lindner W, Hirschböck I (1986) J Liq Chromatogr 9: 551CrossRefGoogle Scholar
  43. 41.
    Lindner W (1983) In: Lawrence JF, Frei RW (eds) Chemical Derivatization in Analytical Chemistry, vol 2. Plenum Press, New YorkGoogle Scholar
  44. 42.
    Pettersson C, Schill G (1988) In: Zief M, Crane L (eds) Chromatographic Chiral Separations. Chromatographic Science Series vol 40. Marcel Deccer Inc, New York, p 283–313Google Scholar
  45. 43.
    Rauch-Puntigam S, Reiter F, Lindner W (1990) J Chromatogr, paper submittedGoogle Scholar
  46. 44.
    Lindner W (1988) In: Zief M, Crane L (eds) Chromatographic Chiral Separations. Chromatographic Science Series. Marcel Dekker, New York, p 91–130Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1991

Authors and Affiliations

There are no affiliations available

Personalised recommendations