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Enantioseparations by Capillary Electrophoresis Using Cyclodextrins as Chiral Selectors

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Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 970))

Abstract

Due to their commercial availability, cyclodextrins are the most frequently used chiral selectors in capillary electrophoresis as documented by the numerous publications in the field. A variety of migration modes can be realized depending on the characteristics of the cyclodextrins and the analytes. The basic considerations regarding the development of a chiral CE method employing cyclodextrins as chiral selectors are briefly discussed. The presented examples illustrate the separation modes of an acidic and a basic analyte with native and charged cyclodextrin derivatives as a function of the pH of the background electrolyte and the cyclodextrin concentration.

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References

  1. Biwer A, Antranikian G, Heinzle E (2002) Enzymatic production of cyclodextrins. Appl Microbiol Biotechnol 59:609–617

    Article  PubMed  CAS  Google Scholar 

  2. Rekharsky MV, Inoue Y (1998) Complexation thermodynamics of cyclodextrins. Chem Rev 98:1875–1917

    Article  PubMed  CAS  Google Scholar 

  3. Del Valle EMM (2004) Cyclodextrins and their uses: a review. Proc Biochem 39:1033–1046

    Article  Google Scholar 

  4. Fanali S (2009) Chiral separations by CE employing CDs. Electrophoresis 30:S203–S210

    Article  PubMed  Google Scholar 

  5. Chankvetadze B (2009) Separation of enantiomers with charged chiral selectors in CE. Electrophoresis 30:S211–S221

    Article  PubMed  Google Scholar 

  6. Scriba GKE, Altria K (2009) Using cyclodextrins to achieve chiral and non-chiral separations in capillary electrophoresis. LCGC Europe 22:420–430

    CAS  Google Scholar 

  7. Scriba GKE (2008) Cyclodextrins in capillary electrophoresis – recent developments and applications. J Sep Sci 31:1991–2001

    Article  PubMed  CAS  Google Scholar 

  8. Juvancz Z, Kendrovics RB, Ivanyi R, Szente L (2008) The role of cyclodextrins in chiral capillary electrophoresis. Electrophoresis 29:1701–1712

    Article  PubMed  CAS  Google Scholar 

  9. Tang W, Ng S-C (2008) Mono-substituted charged cyclodextrins: synthesis and applications in chiral separation. J Sep Sci 31:3246–3256

    Article  PubMed  CAS  Google Scholar 

  10. Schmitt U, Branch SK, Holzgrabe U (2002) Chiral separations by cyclodextrin-modified capillary electrophoresis - determination of the enantiomeric excess. J Sep Sci 25:959–974

    Article  CAS  Google Scholar 

  11. Fanali S (2000) Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors. J Chromatogr A 875:89–122

    Article  PubMed  CAS  Google Scholar 

  12. Schneiderman E, Stalcup AM (2000) Cyclodextrins: a versatile tool in separation science. J Chromatogr B 745:83–102

    Article  CAS  Google Scholar 

  13. Gübitz G, Schmid MG (2010) Cyclodextrin-mediated chiral separations. In: Van Eeckhaut A, Michotte Y (eds) Chiral separations by capillary electrophoresis, Chromatogr Science Series, vol 100. CRC Press, Boca Raton, pp 47–85

    Chapter  Google Scholar 

  14. Chankvetadze B (2006) The application of cyclodextrins for enantioseparations. In: Dodziuk H (ed) Cyclodextrins and their complexes. Wiley-VCH, Weinheim, pp 119–146

    Google Scholar 

  15. Scriba GKE (2011) Fundamental aspects of chiral electromigration techniques and application in pharmaceutical and biomedical analysis. J Pharm Biomed Anal 55:688–701

    Article  PubMed  CAS  Google Scholar 

  16. Chankvetadze B (2007) Enantioseparations by using capillary electromigration techniques. J Chromatogr A 1168:45–70

    Article  PubMed  CAS  Google Scholar 

  17. Chankvetadze B, Blaschke G (2001) Enantioseparations in capillary electromigration techniques: recent developments and future trends. J Chromatogr A 906:309–363

    Article  CAS  Google Scholar 

  18. Gübitz G, Schmid MG (2008) Chiral separation by capillary electromigration techniques. J Chromatogr A 1204:140–156

    Article  PubMed  Google Scholar 

  19. Chankvetadze B (1997) Capillary electrophoresis in chiral analysis. John Wiley & Sons Ltd., Chichester

    Google Scholar 

  20. Van Eeckhaut A, Michotte Y (eds) (2010) Chiral separations by capillary electrophoresis, Chromatogr Science Series, vol 100. CRC Press, Boca Raton

    Google Scholar 

  21. Chankvetadze B, Schulte G, Blaschke G (1997) Nature and design of enantiomer migration order in chiral capillary electrophoresis. Enantiomer 2:157–179

    CAS  Google Scholar 

  22. Chankvetadze B (2002) Enantiomer migration order in chiral capillary electrophoresis. Electrophoresis 23:4022–4035

    Article  PubMed  CAS  Google Scholar 

  23. Hammitzsch-Wiedemann M, Scriba GKE (2009) Mathematical approach by a selectivity model for rationalization of pH- and selector-dependent reversal of the enantiomer migration order in capillary electrophoresis. Anal Chem 81:8765–8773

    Article  PubMed  CAS  Google Scholar 

  24. Scriba GKE (2002) Selected fundamental aspects of chiral enantiomigration techniques and their application to pharmaceutical and biomedical analysis. J Pharm Biomed Anal 27:373–399

    Article  PubMed  CAS  Google Scholar 

  25. Fillet M, Hubert P, Crommen J (2000) Enantiomeric separations of drugs using mixtures of charged and neutral cyclodextrins. J Chromatogr A 875:123–134

    Article  PubMed  CAS  Google Scholar 

  26. Wätzig H, Degenhardt M, Kunkel A (1998) Strategies for capillary electrophoresis. Method development and validation for pharmaceutical and biological applications. Electrophoresis 19:2695–2752

    Article  PubMed  Google Scholar 

  27. Sänger-van de Griend CE, Gröningsson K (1996) Validation of a capillary electrophoresis method for the enantiomeric purity testing of ropivacaine, a new local anaesthetic compound. J Pharm Biomed Anal 14:295–304

    Article  PubMed  Google Scholar 

  28. Skanchy DJ, Xie G-H, Tait RJ, Luna E, Demarest C, Stobaugh JF (1999) Application of sulfobutylether-β-cyclodextrin with specific degrees of substitution for the enantioseparation of pharmaceutical mixtures by capillary electrophoresis. Electrophoresis 20:2638–2649

    Article  PubMed  CAS  Google Scholar 

  29. Wongwan S, Hammitzsch-Wiedemann M, Scriba GKE (2009) Determination of related substances of levodopa including the R-enantiomer by CE. Electrophoresis 30:3891–3896

    Article  PubMed  CAS  Google Scholar 

  30. Rocheleau J-J (2005) Generic capillary electrophoresis conditions for chiral assay in early pharmaceutical development. Electrophoresis 26:2320–2329

    Article  PubMed  CAS  Google Scholar 

  31. Dubský P, Svobodová J, Tesařová E, Gaš B (2010) Enhanced selectivity in CZE multi-chiral selector enantioseparation systems: Proposed separation mechanism. Electrophoresis 31:1435–1441

    PubMed  Google Scholar 

  32. Evans CE, Stalcup AM (2003) Comprehensive strategy for chiral separations using sulfated cyclodextrins in capillary electrophoresis. Chirality 15:709–723

    Article  PubMed  CAS  Google Scholar 

  33. Ates H, Mangelings D, Vander Heyden Y (2008) Fast generic chiral separation strategies using electrophoretic and liquid chromatographic techniques. J Pharm Biomed Anal 48:288–294

    Article  PubMed  CAS  Google Scholar 

  34. Zhou L, Thompson R, Song S, Ellison D, Wywratt JM (2002) A strategic approach to the development of capillary electrophoresis chiral methods for pharmaceutical basic compounds using sulfated cyclodextrins. J Pharm Biomed Anal 27:541–553

    Article  PubMed  CAS  Google Scholar 

  35. Williams BA, Vigh G (1997) Dry look at the CHARM (charged resolving agent migration) model of enantiomer separations by capillary electrophoresis. J Chromatogr A 777:295–309

    Article  CAS  Google Scholar 

  36. Liu L, Nussbaum MA (1999) Systematic screening approach for chiral separations of basic compounds by capillary electrophoresis with modified cyclodextrins. J Pharm Biomed Anal 19:679–684

    Article  PubMed  CAS  Google Scholar 

  37. Jimidar MI, Van Ael W, Van Nyen P, Peeters M, Redlich D, De Smet M (2004) A screening strategy for the development of enantiomeric separation methods in capillary electrophoresis. Electrophoresis 25:2772–2785

    Article  PubMed  CAS  Google Scholar 

  38. Deeb SE, Hasemann P, Wätzig H (2008) Strategies in method development to quantify enantiomeric impurities using CE. Electrophoresis 29:3552–3562

    Article  PubMed  Google Scholar 

  39. Servais A-C, Crommen J, Fillet M (2010) Factors influencing cyclodextrin-mediated chiral separations. In: van Eeckhaut A, Michotte Y (eds) Chiral separations by capillary electrophoresis, Chromatogr Science Series, vol 100. CRC Press, Boca Raton, pp 87–107

    Chapter  Google Scholar 

  40. Sentellas S, Saurina J (2003) Chemometrics in capillary electrophoresis. Part A: method for optimization. J Sep Sci 26:875–885

    Article  CAS  Google Scholar 

  41. Chankvetadze B, Schulte G, Blaschke G (1996) Reversal of enantiomer elution order in capillary electrophoresis using charged and neutral cyclodextrins. J Chromatogr A 732:183–187

    Article  CAS  Google Scholar 

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Correspondence to Gerhard K. E. Scriba .

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Scriba, G.K.E., Jáč, P. (2013). Enantioseparations by Capillary Electrophoresis Using Cyclodextrins as Chiral Selectors. In: Scriba, G. (eds) Chiral Separations. Methods in Molecular Biology, vol 970. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-62703-263-6_17

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  • DOI: https://doi.org/10.1007/978-1-62703-263-6_17

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  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-1-62703-262-9

  • Online ISBN: 978-1-62703-263-6

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