Skip to main content
SpringerLink
Log in

Enantiomers and separation

  • Published:
Chromatographia Aims and scope Submit manuscript

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Cahn, R.S.; Ingold, C.; Prelog, V. Specification of Molecular Chirality,Angew. Chem. Internat. Edit. 1966,5, 385–415.

    Article  CAS  Google Scholar 

  2. Bijvoet, J.M.; Peerdeman, A.F.; van Bommel, A.J. Determination of the absolute configuration of optically active compounds by means of X-rays,Nature 1951,168, 271–272.

    Article  CAS  Google Scholar 

  3. Wilson, A.G.; Brooke, O.G.; Lloyd, H.J.; Robinson, B.F. Mechanism of action of β-Adrenergic Receptor Blocking Agents in Angina Pectoris: Comparison of Action of Propranolol with Dexpropranolol and Practolol,Br. Med. J. 1969,4, 399–401.

    Article  CAS  Google Scholar 

  4. Ariëns, E.J. Stereochemistry, a Basis for Sophisticated Nonsense in Pharmacokinetics and Clinical Pharmacology,Eur. J. Clin. Pharmacol. 1984,26, 663–668.

    Article  Google Scholar 

  5. De Camp, W.H. The FDA Perspective on the Development of Stereoisomers,Chirality 1989,1, 2–6.

    Article  Google Scholar 

  6. Knoche, B.; Blaschke, G. Investigations on thein vitro racemization of thalidomide by high-performance liquid chromatography,J. Chromatogr. A 1994,666, 235–240.

    Article  CAS  Google Scholar 

  7. Caldwell, J.; Hutt, A.J.; Fournel-Gigleux, S. The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences,Biochem. Pharmacol. 1988,37, 105–114.

    Article  CAS  Google Scholar 

  8. Tracy, T.S.; Hall, S.D. Metabolic inversion of (R) Ibuprofen, Epimerization and hydrolysis of ibuprofenyl-coenzyme A,Drug Metab. Dispos. 1992,20, 322–327.

    CAS  Google Scholar 

  9. Drummond, L.; Caldwell, J.; Wilson, H.K. The stereoselectivity of 1,2-phenylethanediol and mandelic acid metabolism and disposition in the rat,Xenobiotica 1990,20, 159–168.

    Article  CAS  Google Scholar 

  10. Testa, B. Mechanisms of Chiral Recognition in Xenobiotic Metabolism and Drug-Receptor Interactions,Chirality 1989,1, 7–9.

    Article  CAS  Google Scholar 

  11. De Camp, W.H. Chiral drugs: the FDA perspective on manufacturing and control,J. Pharm. Biomed. Anal. 1993,11, 1167–1172.

    Article  Google Scholar 

  12. Collins, A.N.; Sheldrake, G.N.; Crosby, J. (eds.), in Chirality in Industry II. Developments in the Manufacture and Applications of Optically Active Compounds, J. Wiley & Sons, New York,1997.

    Google Scholar 

  13. Sheldon, R.A. Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York,1993.

    Google Scholar 

  14. Mazoit, J.X.; Boïco, O.; Samii, K. Myocardial Uptake of Bupivacaine: II. Pharmacokinetics and Pharmacodynamics of Bupivacaine Enantiomers in the Isolated Perfused Rabbit Heart,Anesth. Analg. 1993,77, 477–482.

    CAS  Google Scholar 

  15. Cox, C.R.; Checketts, M.R.; Mackenzie, N.; Scott, N.B.; Bannister, J. Comparison ofS(−)-bupivacaine with racemic (RS)-bupivacaine in supraclavicular brachial plexus block.Br. J. Anaesth. 1998,80, 594–598.

    CAS  Google Scholar 

  16. Kurihara, N.; Miyamoto, J.; Paulson, G.D.; Zeeh, B.; Skidmore, M.W.; Hollingworth, R.M.; Kuiper, H.A. IUPAC Reports on Pesticides (37), Chirality in synthetic agrochemicals: bioactivity and safety consideration.Pure&Appl. Chem. 1997,69, No. 9, 2007–2025.

    CAS  Google Scholar 

  17. Jung, M.; Mayer, S.; Schurig, V. Enantiomer Separation by GC, SFC, and CE on immobilized Polysiloxane-Bonded Cyclodextrins,LC-GC Int 1994,7, 340–347.

    Google Scholar 

  18. Hjertén, S.. Free zone electroporesis,Chromatogr. Rev. 1967,9, 122–219.

    Article  Google Scholar 

  19. Verheggen, Th. P.E.M.; Mikkers, F.E.P.; Everaerts, F.M. Isotachophoresis in narrow-bore tubes. Influence of the diameter of the separation compartment,J. Chromatogr. 1977,132, 205–215.

    Article  CAS  Google Scholar 

  20. Mikkers, F.E.P.; Everaerts, F.M.; Verheggen, Th. P.E.M. High performance zone electrophoresis,J. Chromatogr. 1979,169, 11–20.

    Article  CAS  Google Scholar 

  21. Mikkers, F.E.P.; Everaerts, F.M.; Verheggen, Th. P.E.M. Concentration distributions in free zone electrophoresis,J. Chromatogr. 1979,169, 1–10.

    Article  CAS  Google Scholar 

  22. Jorgenson, J.W.; Lukacs, K.D. Zone Electrophoresis in Open Tubular Glass Capillaries,Anal. Chem. 1981,53, 1298–1302.

    CAS  Google Scholar 

  23. Jorgenson, J.W.; Lukacs, K.D. High-resolution separations, based upon electrophoresis and electroosmosis,J. Chromatogr. 1981,218, 209–216.

    Article  CAS  Google Scholar 

  24. Jorgenson, J.W.; Lukacs, K.D. Free-Zone Electrophoresis in Glass Capillaries,Clin. Chem. 1981,27, 1551–1553.

    CAS  Google Scholar 

  25. Jorgenson, J.W.; Lukacs, K.D. Zone Electrophoresis in Open-Tubular Glass Capillaries: Preliminary Data on Performance,J.H.R.C.&C.C. 1981,4, 230–231.

    CAS  Google Scholar 

  26. Jorgenson, J.W.; Lukacs, K.D. Capillary Zone Electrophoresis,Science 1983,222, 266–272.

    CAS  Google Scholar 

  27. Gassman, E.; Kuo, J.E.; Zare, R.N. Electrokinetic Separation of Chiral Compounds,Science 1985,230, 813–814.

    Google Scholar 

  28. Gozel, P.; Gassman, E.; Michelsen, H.; Zare, R.N. Electrokinetic Resolution of Amino Acid Enantiomers with Copper (II)-Aspartame Support Electrolyte,Anal. Chem. 1987,59, 44–49.

    Article  CAS  Google Scholar 

  29. Terabe, S.; Ozaki, H.; Otsuka, K.; Ando, T. Electrokinetic chromatography with 2-O-carboxymethyl-β-cyclodextrin as a moving ‘stationary’ phase,J. Chromatogr. 1985,332, 211–217.

    Article  CAS  Google Scholar 

  30. Guttman, A.; Paulus, A.; Cohen, A.S.; Grinberg, N.; Karger, B.L., Use of complexing agents for selective separation in high-performance capillary electrophoresis Chiral resolution via cyclodextrins incorporated within polyacrylamide gel columns,J. Chromatogr. 1988,448, 41–53.

    Article  CAS  Google Scholar 

  31. Fanali, S. Separation of optical isomers by capillary zone electrophoresis based on host-guest complexation with cyclodextrins,J. Chromatogr. 1989,474, 441–446.

    Article  CAS  Google Scholar 

  32. Fanali, S.; Bocek, P. Enantiomeric resolution by using capillary zone electrophoresis: Resolution of racemic tryptophan and determination of the enantiomer composition of pharmaceutical epinephrine,Electrophoresis,1990,11, 757–760.

    Article  CAS  Google Scholar 

  33. Fanali, S. Use of cyclodextrins in capillary zone electrophoresis Resolution of terbutaline and propranolol enantiomers,J. Chromatogr. 1991,545, 437–444.

    Article  Google Scholar 

  34. Snopek, J.; Soini, H.; Novotny, M.; Smolkova-Keulemansova, E.; Jelinek, I. Selected applications of cyclodextrin selectors in capillary electrophoresis,J. Chromatogr. 1991,559, 215–222.

    Article  CAS  Google Scholar 

  35. Terabe, S.; Shibata, M.; Miyashita, Y. Chiral separation by electrokinetic chromatography with bile salt micelles,J. Chromatogr. 1989,480, 403–411.

    Article  CAS  Google Scholar 

  36. Cole, R.O.; Sepaniak, M.J.; Hinze, W.L. Optimization of binaphthyl enantiomer separations by capillary zone electrophoresis using mobile phases containing bile salts and organic solvent,J.H.R.C.&C.C. 1990,13, 579–582.

    CAS  Google Scholar 

  37. Dobashi, A.; Ono, T.; Hara, S.; Yamaguchi, J. Optical resolution of enantiomers with chiral mixed micelles by electrokinetic chromatography,Anal. Chem. 1989,61, 1984–1986.

    Article  CAS  Google Scholar 

  38. Nishi, H.; Fukuyama, T.; Terabe, S. Chiral separation by cyclodextrin-modified micellar electrokinetic chromatography,J. Chromatogr. 1991,553, 503–516.

    Article  CAS  Google Scholar 

  39. Ueda, T.; Kitamura, F.; Mitchell, R.; Metcalf, T.; Kuwana, T.; Nakamoto, A. Chiral separation of naphthalene-2,3-dicarboxaldehyde-labeled amino acid enantiomers by cyclodextrin-modified micellar electrokinetic chromatography with laser-induced fluorescence detection,Anal. Chem. 1991,63, 2979–2981.

    Article  CAS  Google Scholar 

Download references

Rights and permissions

Reprints and permissions

About this article

Cite this article

Enantiomers and separation. Chromatographia 54 (Suppl 1), S7–S14 (2001). https://doi.org/10.1007/BF02492890

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02492890

Keywords

Search

Navigation