Skip to main content
SpringerLink
Log in
Book cover

The Separation of Enantiomers by Capillary Electrophoresis pp 78–92Cite as

Other Chiral Selectors

  • Chapter

  • 171 Accesses

Part of the book series: Chromatographia CE Series ((CHROM,volume 6))

Abstract

Chapter 5 covered the applications of cyclodextrins for the separation of enantiomers in CE and some of the benefits. Whilst the cyclodextrins easily constitute the most widely used group of selectors for the separation of enantiomers in CE, a range of other selectors have also been employed. Some of these other selectors have been reported to offer significant benefits over cyclodextrins for example in terms of greater enantioselectivity. As is the case with the cyclodextrins many of the other chiral selectors used in CE are also naturally occurring species or are derived from them. Chapter 6 covers some of the other selectors which have been employed for the separation of enantiomers along with some examples of their application.

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

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

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

    Article  Google Scholar 

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

    Article  Google Scholar 

  3. Schmid, M.G.; Gübitz, G. Direct Enantiomer Separation of Underivatized Amino Acids by Capillary Zone Electrophoresis Based on Ligand Exchange, Enantiomer 1996, 1, 23–27.

    Google Scholar 

  4. Végvari, A.; Schmid, M.G.; Kilar, F.; Gübitz, G. Chiral separation of a-amino acids by ligand-exchange capillary electrophoresis using N-(2-hydroxy-octyl)-L-4hydroxyproline as a selector, Electrophoresis 1998, 19, 2109–2112.

    Article  Google Scholar 

  5. Chen, Z.; Lin, J.-M.; Uchiyama, K.; Hobo, T. Simultaneous Separation of Sixteen Positional and Optical Isomers of the Tryptophan Family by Ligand-Exchange Micellar Electrokinetic Chromatography, Chromatographic 1999, 49, 436–443.

    Article  Google Scholar 

  6. Chen, Z.; Lin, J.-M.; Uchiyama, K.; Hobo, T. Separation Behaviour of Amino Acid Enantiomers in Ligand Exchange Micellar Electrokinetic Chromatography, J. AIicrocolumn Separations 1999, 11, 534–540.

    Article  Google Scholar 

  7. Otsuka, K.; Terabe, S. Effects of methanol and area on optical resolution of phenylthiohydantoin-DL-amino acids by mi-cellar electrokinetic chromatography with sodium N-dodecanoyl-L-valinate, Electrophoresis 1990. 11, 982–984.

    Article  Google Scholar 

  8. Otsuka, K.; Kawahara, J.; Tatekawa, K.; Terabe, S. Chiral separations by micellar electrokinetic chromatography with sodium N-dodecanoyl-L-valinate, J. Chromatogr. 1991, 559, 209–214.

    Article  Google Scholar 

  9. Mazzeo, J.R.; Grover. E.R.; Swartz, M.E.; Petersen, J.S. Novel chiral surfactant for the separation of enantiomers by micellar electrokinetic chromatography, J. Chromatogr. A 1994. 680, 125–135.

    Article  Google Scholar 

  10. Wang, J.; Warner, I.M. Combined polymerized chiral micelle and -y -cyclodextrin for chiral separations in capillary electrophoresis, J. Chromatogr. A 1995, 711, 297–304.

    Article  Google Scholar 

  11. Shamsi, S.A.; Warner, I.M. Monomeric and polymeric chiral surfactants as pseudo-stationary phases for chiral separations, Electrophoresis 1997, 18,853–872

    Google Scholar 

  12. Nishi, H.; Fukuyama, T.; Matsuo, M. Terabe, S. Chiral Separation of Optical Isomeric Drugs Using Micellar Electrokinetic Chromatography and Bile Salts, J. Microcolmnn Separations 1989, 1, 234,241.

    Article  Google Scholar 

  13. Amini. A.: Beijersten, I.; Pettersson, C.; Westerland, D. Enantiomeric separation of local anaesthetic drugs by micellar electrokinetic capillary chromatography with taurodeoxycholate as chiral selector, J. Chromatogr. A 1996, 737, 301–313.

    Article  Google Scholar 

  14. Okafo, G.N.; Camilleri, P. Direct Chiral Resolution of Amino Acid Derivatives by Capillary Electrophoresis, J. Microcolmnn Separations 1993, 5, 149–153.

    Article  Google Scholar 

  15. Otsuka, K.; Terabe, S. Enantiomeric resolution by micellar electrokinetic chromatography with chiral surfactants, J. Chromatogr. 1990, 515,221 —226.

    Google Scholar 

  16. Mechref, Y.; Rassi, Z.E. Comparison of alkylglycoside surfactants in enantioseparation by capillary electrophoresis, Electrophoresis 1997, 18, 912–918.

    Article  Google Scholar 

  17. Ingelse, B.A.; Flieget, M.; Claessen, H.A.; Everaerts, F.M. Ergot alkaloids as chiral selectors in capillary electrophoresis determination of separation mechanism, J. Chromatogr. A 1996, 755, 251–259.

    Article  Google Scholar 

  18. Ingelse, B.A.; Reijenga, J.C.; Everaerts, F.M. Reversed determination of the formation constants of 1-allylterguride with mandelic acid optical isomers using capillary electrophoresis, J. Chromatogr. A 1997, 772,179–184

    Google Scholar 

  19. Nair, U.B.; Armstrong, D.W.; Hinze, W.L. Characterization and Evaluation of d-(+)-Tubocurarine Chloride as a Chiral Selector for Capillary Electrophoresis Enantioseparations, Anal. Chem. 1998, 70, 1059–1065.

    Article  Google Scholar 

  20. Kuhn, R.; Erni, F.; Bereuter, T.; Häusler, J. Chiral Recognition and Enantiomeric Resolution Based on Host-Guest Cornplexation with Crown Ethers in Capillary Zone Electrophoresis, Anal. Chem. 1992, 64, 2815–2820.

    Article  Google Scholar 

  21. Kuhn, R.; Stoecklin, F.; Erni, F. Chiral Separations by Host-Guest Complexation with Cydodextrin and Crown Ether in Capillary Zone Electrophoresis, Chromatographia 1992, 33, 32–36.

    Article  Google Scholar 

  22. Verleysen, K.; Vandijck, J.; Schelfaut, M.; Sandra, P. Enantiomeric Separations in Capillary Electrophoresis Using 18Crown-6-tetracarboxylic Acid (18CH4) as Buffer Additive, J. High Resol. Chromatogr. 1998,2/, 323–331.

    Google Scholar 

  23. Verleysen, K.: Sandra, P. Enantiomeric Separation of Some Amino Acids and Derivatives by Capillary Electrophoresis with 18-Crown-6-Tetracarboxylic Acid as Chiral Selector, J. Micracalunm Separations 1999, 11, 37–43.

    Article  Google Scholar 

  24. Barker, G.E.; Russo, P.; Hartwick, R.A. Chiral Separation of Leucovorin with Bovine Serum Albumin Using Affinity Capillary Electrophoresis, Anal. Cheat. 1992, 64, 3024–3028.

    Article  Google Scholar 

  25. Vespalec, R.: Sustacek, V.; Bocek, P. Prospects of dissolved albumin as a chiral selector in capillary zone electrophoresis, J. Chromatogr. 1993, 638, 255–261.

    Article  Google Scholar 

  26. Vattcheva, L.; Mohammad, J.; Pettersson, G.: Hjertén, S. Chiral separation of)blockers by high-performance capillary electrophoresis based on non-immobilized cellulase as enantioselective protein, J. Chromatogr. 1993, 638, 263–267.

    Article  Google Scholar 

  27. Tanaka, Y.; Terabe, S.; Partial separation zone technique for the separation of enantiomers by affinity electrokinetic chromatography with proteins as chiral pseudo-stationary phases. J. Chromatogr. A 1995, 694, 277–284.

    Article  Google Scholar 

  28. Amini, A.; Pettersson, C.; Westerlund, D. Enantioresolution of disopyramide by capillary affinity electrokinetic chromatography with human ar-acid glycoprotein (AGP) as chiral selector applying a partial filling technique, Electrophoresis 1997, 18, 950–957.

    Google Scholar 

  29. Haginaka, J.; Kanasugi, N. Separation of basic drug enantiomers by capillary zone electrophoresis using ovoglycoprotein as a chiral selector, J. Chromatogr. A 1997, 782, 281–288.

    Article  Google Scholar 

  30. Tanaka, Y.; Terabe, S. Studies on Enantioselectivities of Avidin, Avidin-Biotin Complex and Streptavidin by Affinity Capillary Electrophoresis, Chromatographia 1999, 49, 489–495.

    Article  Google Scholar 

  31. Tanaka, Y.: Matsubara, N.; Terabe, S. Separation of enantiomers by affinity electrokinetic chromatography using avidin, Electrophoresis 1994, 15, 848–853.

    Article  Google Scholar 

  32. Armstrong. D.W.; Rundlett, K.L.; Chen, J: R. Evaluation of the Macrocyclic Antibiotic Vancomycin as a Chiral Selector for Capillary Electrophoresis, Chirality 1994, 6, 496–509.

    Article  Google Scholar 

  33. Armstrong, D.W.; Rundlett, K.; Reid III, G.L. Use of a Macrocyclic Antibiotic, Rifamycin B, Indirect Detection for the Resolution of Racemic Amino Alcohols by CE, Anal. Chem. 1994, 66, 1690–1695.

    Article  Google Scholar 

  34. Armstrong, D.W; Tang, Y.; Chen, S.; Zhou, Y.; Chen,.1.-12.; Bagwill, C. Macro-cyclic antibiotics as a new class of chiral selector for liquid chromatography, Anal. Chem. 1994, 66, 1473–1484.

    Article  Google Scholar 

  35. Carpenter, J.L.; Camilleri, P.; Dhanak, D.; Goodall, D. A study of the binding of vancomycin to dipeptides using capillary electrophoresis, J. Chem. Soc. Chem. Commun. 1992, 804–806.

    Google Scholar 

  36. Liu, J.; Volk, K.J.; Lee, M.S.; Pacci, M.; Handwerger, S. Binding Studies of Vancomycin to the Cytoplasmic Peptidoglycan Precursors by Affinity Capillary Electrophoresis, Anal. Chem. 1994, 66, 24122416.

    Google Scholar 

  37. Vespalec, R.; Corstjens, H.; Billiet, H.A.H.; Frank, J.; Luyben, K.Ch.A.M. Enantiomeric Separation of Sulfur-and Selenium-Containing Amino Acids by Capillary Electrophoresis Using Vancomycin as a Chiral Selector, Anal. Chem. 1995, 67, 3223–3228.

    Article  Google Scholar 

  38. Rundlett, K.L.; Armstrong, D.W. Effect of Micelles and Mixed Micelles on Efficiency and Selectivity of Antibiotic-Based Capillary Electrophoretic Enantioseparalions, Anal. Chem. 1995, 67, 2088–2095.

    Article  Google Scholar 

  39. Fanali, S.; Desiderio, C.; Aturki, Z. Enantiomeric resolution study by capillary electrophoresis Selection of the appropriate chiral selector, J. Chromatogr. A 1997, 772, 185–194.

    Article  Google Scholar 

  40. Fanali, S.; Desiderio, C.; Schulte, G.; Heitmeier, S.; Strickman, D.; Chankvetadze, B.; Blaschke, G. Chiral capillary electrophoresis-electrospray mass spectrometry coupling using vancomycin as chiral selector, J. Chromatogr. A 1998, 800, 6976.

    Google Scholar 

  41. Reilly, J.; Risley, D.S. The Separation of Enantiomers by Countercurrent CE Using the Macrocyclic Antibiotic A82846B, LC-GC International September, 1998 598606.

    Google Scholar 

  42. Armstrong D.W.; Gasper, M.P.; Rundlett, K.L. Highly enantioselective capillary electrophoretic separations with dilute solutions of the macrocyclic antibiotic ristocetin A, J. Chromatogr. A 1995.689, 285304.

    Google Scholar 

  43. Gasper, M.P.; Berthod, A.; Nair, U.B.; Armstrong, D.W. Comparison and Modeling Study of Vancomycin, Ristocetin A, Teicoplanin for CE Enantioseparations, Anal. Chem. 1996,68, 2501–2514.

    Article  Google Scholar 

  44. Carotti, A.; Di Gioia, F.; Cellamare, S.; Fanali, S. Teicoplanin-Based Enantiomeric Separations in CZE Using a Partial Filling Technique, J. High Resol. Chromatogr. 1999, 22, 315–321.

    Article  Google Scholar 

  45. Wan, H.; Blomberg, L.G. Chiral separation of DL-peptides and enantioselective interactions between teicoplanin and D-peptides in capillary electrophoresis, Electraphoresis 1997, 18, 943–949.

    Article  Google Scholar 

  46. D’ Hulst, A.; Verbeke, N. Chiral separation by capillary electrophoresis with oligosaccharides, J. Chromatogr. 1992, 608, 275–287.

    Article  Google Scholar 

  47. Chankvetadze, B.; Saito, M.; Yashitna, E.; Okamoto, Y. Enantioseparation using selected polysaccharides as chiral buffer additives in capillary electrophoresis, J. Chromatogr. A 1997, 773, 331–338.

    Article  Google Scholar 

  48. Bowser, M.T.; Kranack, A.R.; Chen, D.D.Y. Analyte-additive interactions in non-aqueous capillary electrophoresis: a critical review, TRAC 1998, 17, 424–434.

    Google Scholar 

  49. Wang, F.; Kbaledi, M.G. Chiral separations by Nonaqueous Capillary Electrophoresis, Anal. Chem. 1996 68,34603467.

    Google Scholar 

  50. Wang, F.; Khaledi, M.G. Nonaqueous capillary electrophoresis chiral separations with quaternary ammonium β-cyclodextrin, J. Chromatogr. A 1998 817,121(28.

    Google Scholar 

  51. Vincent, J.B.; Vigh, G. Nonaqueous capillary electrophoretic separation of enantiomers using the single-isomer heptakis(2,3diacetyl-6-sulfato)-ß-cyclodextrin as chiral resolving agent, J. Chromatogr. A 1998, 816, 233–241.

    Article  Google Scholar 

  52. Bjrnsdottir, I; Hansen, S.H.; Terabe, S. Chiral separation in non-aqueous media by capillary electrophoresis using the ion-pair principle, J. Chromatogr. A 1996, 745, 37–44.

    Article  Google Scholar 

  53. Karbaum, A.; Jira, T. Chiral separation of unmodified amino acids with non-aqueous capillary electrophoresis based on the ligand-exchange principle, J. Chromatogr. A 2000, 874, 285–292.

    Article  Google Scholar 

  54. Mardones, C.; Rios, A.; Valcarcel, M.; Cicciarelli, R. Enantiomeric separation of D- and L-carnitine by integrating on-line derivatisation with capillary electrophoresis, J. Chromatogr. A 1999 849,609616.

    Google Scholar 

  55. Thorsén, G.; Engström, A.; Josefsson, B. Enantiomeric determination of amino componds with high sensitivity using the chiral reagents (+)- and (—)-l-(9-anthryl)2-propyl chloroformate, J. Chromatog. A 1997, 786, 347–354.

    Article  Google Scholar 

  56. Liu, Y.-M; Schneider, M.; Sticha, C.M.; Toyooka, T.; Sweedler, J.V. Separation of amino acid and peptide stereoisomers by nonionic micelle-mediated capillary electrophoresis after chiral derivatisation, J. Chromatogr. A 1998, 800, 345–354.

    Article  Google Scholar 

  57. Jorgenson, J. W; Lukacs, K.D. High-resolution separations, based upon electrophoresis and electroosmosis, J. Chromatogr. 1981,2/8 209–216.

    Google Scholar 

  58. Neue, U.D. HPLC Columns Theory, Technology, Practice, Wiley-VCH, New York, 1997.

    Google Scholar 

  59. Knox, J.H.; Grant, LH. Electrochromatography in Packed Tubes Using 1.5 to 50 um Silica and ODS Bonded Silica Gels, Chromatographia 1991, 32, 317–328.

    Article  Google Scholar 

  60. Adam, Th.; Lüdtke, S.; Unger, K.K. Packing and Stationary Phase Design for Capillary Electroendosmotic Chromatography (CEC), Chromatographic 1999 49,49 —55.

    Google Scholar 

  61. Wen, E.; Asiaie, R.; Horvath, Cs. Dynamics of capillary electrochromatography Il. Comparison of column efficiency parameters in microscale high-performance liquid chromatography and capillary electrochromatography, J. Chromatogr. A 1999. 855, 349–366.

    Article  Google Scholar 

  62. Li, S.; Lloyd, D.K. Direct Chiral Separations by Capillary Electrophoresis Using Capillaries Packed with at-Acid Glycoprotein Chiral Stationary Phase, Anal. Chem. 1993, 65, 3684–3690.

    Article  Google Scholar 

  63. Carter-Finch, A.S.; Smith, N.W. Enantiomeric separations by capillary electrochromatography using a macrocyclic antibiotic chiral stationary phase, J. Chromatogr. A 1999 848, 375–385

    Google Scholar 

  64. Wolf, C.; Spence, P.L.; Pirkle, W.H.; Derrico, E.M.; Cavender, D.M.; Rozing, G.P. Enantioseparations by electrochromatography with packed capillaries, J. Chromatogr. A 1997, 782, 175–179.

    Article  Google Scholar 

  65. Lämmerlrofer, M.; Lindner, W. High-efficiency chiral separations of N-derivatized amino acids by packed-capillary electrochromatography with a quinine-based chiral anion-exchange type stationary phase, J. Chromatog, A 1998 829,115125.

    Google Scholar 

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

    Google Scholar 

  67. Koide, T.; Ueno, K. Enantiomeric Separations of Acidic and Neutral Compounds by Capillary Electrochromatography with ß-Cyclodextrin-Bonded Positively Charged Polyacrylamide Gels, J. High Resol. Chronmtogr. 2000, 23, 59–66.

    Article  Google Scholar 

  68. Nilsson, S.; Schweitz, L.; Petersson, M. Three approaches to enantiomer separation of ß-adrenergic antagonists by capillary electrochromatography. Electrophoresis 1997, 18, 884–890.

    Article  Google Scholar 

  69. Mayer, S.; Schurig, V. Enantiomer Separation by Electrochromatography on Capillaries Coated With Chiralsil-Dex. J. High Rees!. Chromatog,1992,15,129–131.

    Google Scholar 

  70. Mayer, S.; Schurig, V. Enantiomer separation by electrochromatography in open tubular columns coated with ChirasilDex..l. Liq. Chromatogr. 1993 16,915931.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Chinley, UK

    Stephen Wren

  2. Berger Instruments Inc., 130 Executive Drive, Suite 2A, 19702, Newark, DE, USA

    T. A. Berger

  3. Institut für Klinische Chemie Klinikum, Universität München, 81366, München, Germany

    K.-S. Boos

  4. Instrumentelle Analytik — Umweltanalytik, Universität des Saarlandes, 66041, Saarbrücken, Germany

    H. Engelhardt

  5. Delryn, Vicarage Lane, CH64 5TJ, Burton, South Wirral, UK

    E. R. Adlard

  6. 78 Blinco Grove, CB1 7TS, Cambridge, UK

    I. W. Davies

  7. Analytical Evaluation Gp., Glaxo R&D, SG12 0DP, Ware, Herts, UK

    K. D. Altria

  8. 23 Highbury Road, NG12 5JB, Keyworth, Notts., UK

    R. Stock

Authors
  1. Stephen Wren
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. A. Berger
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K.-S. Boos
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. H. Engelhardt
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. R. Adlard
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. W. Davies
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. K. D. Altria
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. R. Stock
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Berger Instruments Inc., 130 Executive Drive, Suite 2A, 19702, Newark, DE, USA

    T. A. Berger

  2. Institut für Klinische Chemie Klinikum, Universität München, 81366, München, Germany

    K.-S. Boos

  3. Instrumentelle Analytik — Umweltanalytik, Universität des Saarlandes, 66041, Saarbrücken, Germany

    H. Engelhardt

  4. Delryn, Vicarage Lane, CH64 5TJ, Burton, South Wirral, UK

    E. R. Adlard

  5. 78 Blinco Grove, CB1 7TS, Cambridge, UK

    I. W. Davies

  6. Analytical Evaluation Gp., Glaxo R&D, SG12 0DP, Ware, Herts, UK

    K. D. Altria

  7. 23 Highbury Road, NG12 5JB, Keyworth, Notts., UK

    R. Stock

Rights and permissions

Reprints and permissions

Copyright information

© 2001 Friedr. Vieweg & Sohn Verlagsgesellschaft mbH

About this chapter

Cite this chapter

Wren, S. et al. (2001). Other Chiral Selectors. In: Berger, T.A., et al. The Separation of Enantiomers by Capillary Electrophoresis. Chromatographia CE Series, vol 6. Vieweg+Teubner Verlag, Wiesbaden. https://doi.org/10.1007/978-3-322-83141-5_6

Download citation

  • DOI: https://doi.org/10.1007/978-3-322-83141-5_6

  • Publisher Name: Vieweg+Teubner Verlag, Wiesbaden

  • Print ISBN: 978-3-322-83143-9

  • Online ISBN: 978-3-322-83141-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation