Skip to main content
SpringerLink
Log in

Cyclodextrin-Mediated Enantioseparations by Capillary Electrochromatography

  • Protocol
  • First Online:
Chiral Separations

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

Abstract

Immobilized cyclodextrin derivatives are used as chiral selectors in various modes of capillary electrochromatography (CEC). The present chapter describes three techniques in detail utilizing CDs in CEC: (1) open-tubular capillary electrochromatography (o-CEC), (2) packed capillary electrochromatography (p-CEC), and (3) monolithic capillary electrochromatography (rod-CEC). Nanoparticle pseudostationary phase capillary electrochromatography (psp-CEC) is briefly discussed.

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

Access this chapter

Log in via an institution
Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 159.00
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover 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

Institutional subscriptions

References

  1. Mangelings D, Vander Heyden Y (2011) Enantioselective capillary electrochromatography: Recent developments and new trends. Electrophoresis 32:2583–2601

    Article  PubMed  CAS  Google Scholar 

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

    Article  PubMed  Google Scholar 

  3. Wistuba D, Schurig V (2009) The separation of enantiomers on modified cyclodextrins by capillary electrochromatography (CEC). LCGC Europe 22:60–69

    CAS  Google Scholar 

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

    Article  PubMed  Google Scholar 

  5. Chankvetadze B (2007) Enantioseparations by using capillary electrophoretic techniques: The story of 20 and a few more years. J Chromatogr A 1168:45–70

    Article  PubMed  CAS  Google Scholar 

  6. Scriba GKE (2003) Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: An update. Electrophoresis 24:2409–2421

    Article  PubMed  CAS  Google Scholar 

  7. Schurig V, Wistuba D (1999) Recent innovations in enantiomer separation by capillary electrochromatography utilizing modified cyclodextrins as stationary phases. Electrophoresis 20:2313–2328

    Article  PubMed  CAS  Google Scholar 

  8. Simó C, Garcia-Cañas V, Cifuentes A (2010) Chiral CE-MS. Electrophoresis 31: 1442–1456

    Article  PubMed  Google Scholar 

  9. Guttman A, Paulus A, Cohen AS, Grinberg N, Karger BL (1988) Use of complexing agents for selective separations in high-performance capillary electrophoresis: Chiral resolution via cyclodextrins incorporated within polyacrylamide gel columns. J Chromatogr 448:41–53

    Article  CAS  Google Scholar 

  10. Yang L, Chen C, Liu X, Shi J, Wang G, Zhu L, Guo L, Glennon JD, Scully NM, Doherty BE (2010) Use of cyclodextrin-modified gold nanoparticles for enantioseparations of drugs and amino acids based on pseudostationary phase-capillary electrochromatography. Electrophoresis 31:1697–1705

    Article  PubMed  CAS  Google Scholar 

  11. Na N, Hu Y, Ouyang J, Baeyens WR, Delanghe JR, Taes YE, Xie M, Chen H, Yang Y (2006) On the use of dispersed nanoparticles modified with single layer β-cyclodextrin as chiral selector to enhance enantioseparation of clenbuterol with capillary electrophoresis. Talanta 69:866–872

    Article  PubMed  CAS  Google Scholar 

  12. Li M, Liu X, Jiang F, Guo L, Yang L (2011) Enantioselective open-tubular capillary electrochromatography using cyclodextrin-modified gold nanoparticles as stationary phase. J Chromatogr A 1218:3725–3729

    Article  PubMed  CAS  Google Scholar 

  13. Mayer S, Schurig V (1992) Enantiomer separation by electrochromatography on capillaries coated with Chirasil-Dex. J High Resolut Chromatogr 15:129–131

    Article  CAS  Google Scholar 

  14. Mayer S, Schurig V (1993) Enantiomer ­separation by electrochromatography in open tubular columns coated with Chirasil-Dex. J Liq Chromatogr 16:915–931

    Article  CAS  Google Scholar 

  15. Schurig V, Mayer S (2001) Separation of enantiomers by open capillary electrochromatography on polysiloxane-bonded per­methyl-β-cyclodextrin. J Biochem Biophys Methods 48:117–141

    Article  PubMed  CAS  Google Scholar 

  16. Jakubetz H, Juza M, Schurig V (1998) Dual chiral recognition system involving cyclodextrin derivatives in capillary electrophoresis II Enhancement of enantioselectivity. Electrophoresis 19:738–744

    Article  PubMed  CAS  Google Scholar 

  17. Mayer S, Schleimer M, Schurig V (1994) Dual chiral recognition system involving cyclodextrin derivatives in capillary electrophoresis. J Microcol 6:43–48

    Article  CAS  Google Scholar 

  18. Schurig V, Jung M, Mayer S, Fluck M, Negura S, Jakubetz H (1995) Unified enantioselective capillary chromatography on a Chirasil-DEX stationary phase. Advantages of column miniaturization. J Chromatogr A 694:119–128

    Article  PubMed  CAS  Google Scholar 

  19. Armstrong DW, Tang Y, Ward T, Nichols M (1993) Derivatized cyclodextrins immobilized on fused-silica capillaries for enantiomeric separations via capillary electrophoresis, gas chromatography, or supercritical fluid chromatography. Anal Chem 65:1114–1117

    Article  CAS  Google Scholar 

  20. Wang Y, Zeng Z, Guan N, Cheng J (2001) Sol–gel technique fort he preparation of β-cyclodextrin derivative stationary phase in open-tubular capillary electrochromatography. Electrophoresis 22:2167–2172

    Article  PubMed  CAS  Google Scholar 

  21. Hongjun E, Su P, Farooq MU, Yang Y (2010) Microwave-assisted preparation of a β-cyclodextrin-based stationary phase for open tubular capillary electrochromatography. Anal Lett 43:2372–2380

    Article  CAS  Google Scholar 

  22. Li S, Lloyd DK (1994) Packed-capillary electrophoretic separation of the enantiomers of neutral and anionic compounds using β-cyclodextrin as a chiral selector: effect of operating parameters and comparison with free-solution capillary electrophoresis. J Chromatogr A 666: 321–335

    Article  CAS  Google Scholar 

  23. Lelièvre F, Yan C, Zare RN, Gareil P (1996) Capillary electrochromatography: operating characteristics and enantiomer separations. J Chromatogr A 723:145–156

    Article  Google Scholar 

  24. Wistuba D, Czesla H, Roeder M, Schurig V (1998) Enantiomer separation by pressure-supported electrochromatography using capillaries packed with permethyl-β-cyclodextrin stationary phase. J Chromatogr A 815: 183–188

    Article  PubMed  CAS  Google Scholar 

  25. Wistuba D, Schurig V (1999) Enantiomer separation by pressure-supported electrochromatography using capillaries packed with Chirasil-Dex polymer-coated silica. Electro-phoresis 20:2779–2785

    Article  PubMed  CAS  Google Scholar 

  26. Zhou M, Lv X, Xie Y, Yan C, Gao R (2005) Chromatographic evaluation of perphenylcarbamoylated β-cyclodextrin bonded stationary phase for micro-high performance liquid chromatography and pressurized capillary electrochromatography. Anal Chim Acta 547: 158–164

    Article  CAS  Google Scholar 

  27. Lin B, Shi Z-G, Zhang H-J, Ng S-C, Feng Y-Q (2006) Perphenylcarbamoylated β-cyclodextrin bonded-silica particles as stationary phase for enantioseparation by pressure-assisted capillary electrochromatography. Electrophoresis 27:3057–3065

    Article  PubMed  CAS  Google Scholar 

  28. Von Brocke A, Wistuba D, Gfrörer P, Stahl M, Schurig V, Bayer E (2002) On-line coupling of packed capillary electrochromatography with coordination ion spray-mass spectrometry for the separation of enantiomers. Electrophoresis 23:2963–2972

    Article  Google Scholar 

  29. Wistuba D, Cabrera K, Schurig V (2001) Enantiomer separation by nonaqueous and aqueous capillary electrochromatography on cyclodextrin stationary phase. Electrophoresis 22:2600–2605

    Article  PubMed  CAS  Google Scholar 

  30. Wang Y, Xiao Y, Tan TTY, Ng S-C (2008) Click chemistry for facile immobilization of cyclodextrin derivatives onto silica as chiral stationary phases. Tetrahedron Lett 49:5190–5191

    Article  CAS  Google Scholar 

  31. Wang Y, Xiao Y, Tan TTY, Ng S-C (2009) Application of Click-chemistry-based perphenylcarbamated β-CD chiral stationary phase in CEC. Electrophoresis 30:705–711

    Article  PubMed  CAS  Google Scholar 

  32. Li LS, Wang Y, Young DJ, Ng S-C, Tan TTY (2010) Monodispersed submicron porous silica particles functionalized with CD derivatives for chiral CEC. Electrophoresis 31:378–387

    Article  PubMed  Google Scholar 

  33. Kang J, Wistuba D, Schurig V (2002) A silica monolithic column prepared by the sol–gel process for enantiomeric separation by capillary electrochromatography. Electrophoresis 23:1116–1120

    Article  PubMed  CAS  Google Scholar 

  34. Chen Z, Ozawa H, Uchiyama H, Hobo T (2003) Cyclodextrin-modified monolithic columns for resolving dansyl amino acid enantiomers and positional isomers by capillary electrochromatography. Electrophoresis 24: 2550–2558

    Article  PubMed  CAS  Google Scholar 

  35. Hsieh M-L, Li G-Y, Chau L-K, And Hon Y-S (2008) Single-step approach to β-cyclodextrin-bonded silica as monolithic stationary phases for CEC. J Sep Sci 31:1819–1827

    Article  PubMed  CAS  Google Scholar 

  36. Yuan R, Wang Y, Ding G (2010) Enantiomeric separation by capillary electrochromatography on a sulfated poly β-cyclodextrin modified silica-based monolith. Anal Sci 26:943–947

    Article  PubMed  CAS  Google Scholar 

  37. Wistuba D, Schurig V (2000) Enantiomer separation by capillary electrochromatography on a cyclodextrin-modified monolith. Electro-phoresis 21:3152–3159

    Article  PubMed  CAS  Google Scholar 

  38. Wistuba D, Banspach L, Schurig V (2005) Enantiomeric separation by capillary electrochromatography using monolithic capillaries with sol–gel-glued cyclodextrin-modified silica particles. Electrophoresis 26:2019–2026

    Article  PubMed  CAS  Google Scholar 

  39. Schurig V, Schmalzing D, Mühleck U et al (1990) Gas chromatographic enantiomer separation on polysiloxane-anchored permethyl-β-cyclodextrin (Chirasil-Dex). J High Resolut Chromatogr 13:713–717

    Article  CAS  Google Scholar 

  40. Jung M, Schurig V (1993) Enantiomeric separation by GC on Chirasil-Dex: systematic study of cyclodextrin concentration, polarity, immobilization, and column stability. J Microcol 5: 11–22

    Article  CAS  Google Scholar 

  41. Cousin H, Trapp O, Peulon-Agasse V, Pannecoucke X, Banspach L, Trapp G, Jiang Z, Combret JC, Schurig V (2003) Synthesis, NMR spectroscopic characterization and polysiloxane-based immobilization of the three regioisomeric monooctenylpermethyl-β-cyclodextrins and their application in enantioselective GC. Eur J Org Chem 17:3273–3287.

    Google Scholar 

  42. Schurig V, Negura S, Mayer S, Reich S (1996) Enantiomer separation on a Chirasil-Dex-polymer-coated stationary phase by conventional and micro-packed high-performance liquid chromatography. J Chromatogr A 755: 299–307

    Article  PubMed  CAS  Google Scholar 

  43. Asaie R, Huang X, Farnan D, Horváth C (1998) Sintered octadecylsilica as monolithic column packing in capillary electrochromatography and micro high-performance ­liquid chromatography. J Chromatogr A 806: 251–263

    Article  Google Scholar 

  44. Tanaka N, Nagayama H, Kobayashi H et al (2000) Monolithic silica columns for HPLC, micro-HPLC, and CEC. J High Resolut Chromatogr 23:111–116

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany

    Dorothee Wistuba & Volker Schurig

Authors
  1. Dorothee Wistuba
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Volker Schurig
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dorothee Wistuba .

Editor information

Editors and Affiliations

  1. , Department of Pharmaceutical Chemistry, Friedrich-Schiller-University Jena, Philosophenweg 14, Jena, 07743, Germany

    Gerhard K. E. Scriba

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer Science+Business Media, LLC

About this protocol

Cite this protocol

Wistuba, D., Schurig, V. (2013). Cyclodextrin-Mediated Enantioseparations by Capillary Electrochromatography. 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_32

Download citation

  • DOI: https://doi.org/10.1007/978-1-62703-263-6_32

  • Published:

  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-1-62703-262-9

  • Online ISBN: 978-1-62703-263-6

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics

Search

Navigation