Abstract
Due to their structural variability and their commercial availability, cyclodextrins are the most frequently used chiral selectors in capillary electrophoresis. 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 concentration of the cyclodextrin.
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Biwer A, Antranikian G, Heinzle E (2002) Enzymatic production of cyclodextrins. Appl Microbiol Biotechnol 59:609–617
Jin Z (2013) Cyclodextrin chemistry. World Scientific Publishing, Singapore
Bilensoy E (ed) (2011) Cyclodextrins in pharmaceutics, cosmetics and biomedicine. Current and future industrial applications. Wiley, Hoboken
Dodziuk H (ed) (2006) Cyclodextrins and their complexes: chemistry, analytical methods, applications. Wiley-VCH, Weinheim
Iacovino R, Caso JV, Di Donato C et al (2017) Cyclodextrins as complexing agents: preparation and applications. Curr Org Chem 21:162–176
Zhu Q, Scriba GKE (2016) Advances in the use of cyclodextrins as chiral selectors in capillary electrokinetic chromatography: fundamentals and applications. Chromatographia 79:1403–1435
Saz JM, Marina ML (2016) Recent advances on the use of cyclodextrins in the chiral analysis of drugs by capillary electrophoresis. J Chromatogr A 1467:79–94
Cucinotta V, Contino A, Giuffrida A et al (2010) Application of charged single isomer derivatives of cyclodextrins in capillary electrophoresis for chiral analysis. J Chromatogr A 1217:953–967
Řezanka P, Navrátilová K, Řezanka M et al (2014) Application of cyclodextrins in chiral capillary electrophoresis. Electrophoresis 35:2701–2721
Escuder-Gilabert L, Martín-Biosca Y, Medina-Hernández MJ et al (2014) Cyclodextrins in capillary electrophoresis: recent developments and new trends. J Chromatogr A 1357:2–23
Zhou J, Tang J, Tang W (2015) Recent development of cationic cyclodextrins for chiral separation. Trends Anal Chem 65:22–29
Fanali S (2009) Chiral separations by CE employing CDs. Electrophoresis 30:S203–S210
Chankvetadze B (2009) Separation of enantiomers with charged chiral selectors in CE. Electrophoresis 30:S211–S221
Scriba GKE (2008) Cyclodextrins in capillary electrophoresis enantioseparations—recent developments and applications. J Sep Sci 31:1991–2011
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
Chankvetadze B (2006) The application of cyclodextrins for enantioseparations. In: Dodziuk H (ed) Cyclodextrins and their complexes: chemistry, analytical methods, applications. Wiley-VCH, Weinheim, pp 119–146
Tang W, Ng SC, Sun D (2013) Modified cyclodextrins for chiral separation. Springer, New York
Sánchez-López E, Marina ML, Crego AL (2016) Improving the sensitivity in chiral capillary electrophoresis. Electrophoresis 37:19–34
Jáč P, Scriba GKE (2013) Recent advances in electrodriven enantioseparations. J Sep Sci 36:52–74
Scriba GKE (2013) Differentiation of enantiomers by capillary electrophoresis. Top Curr Chem 340:209–276
Scriba GKE (2011) Fundamental aspects of chiral electromigration techniques and application in pharmaceutical and biomedical analysis. J Pharm Biomed Anal 55:688–701
Chankvetadze B (2007) Enantioseparations by using capillary electrophoretic techniques. The story of 20 and a few more years. J Chromatogr A 1168:45–70
Chankvetadze B (1997) Capillary electrophoresis in chiral analysis. Wiley, Chichester
Van Eeckhaut A, Michotte Y (eds) (2010) Chiral separations by capillary electrophoresis. Chromatogr Science Series, vol. 100. CRC Press, Boca Raton
Biedermann F, Nau WM, Schneider HJ (2014) The hydrophobic effect revisited—studies with supramolecular complexes imply high-energy water as noncovalent driving force. Angew Chem Int Ed 53:11158–11171
Schneider HJ (2009) Binding mechanisms in supramolecular complexes. Angew Chem Int Ed 48:3924–3977
Chankvetadze B (2002) Enantiomer migration order in chiral capillary electrophoresis. Electrophoresis 23:4022–4035
Hammitzsch-Wiedemann M, Scriba GKE (2009) Mathematical approach by a selectivity model for rationalization of pH- and selector concentration-dependent reversal of the enantiomer migration order in capillary electrophoresis. Anal Chem 81:8765–8773
Fillet M, Hubert P, Crommen J (2000) Enantiomeric separations of drugs using mixtures of charged and neutral cyclodextrins. J Chromatogr A 875:123–134
Wätzig H, Degenhardt M, Kunkel A (1998) Strategies for capillary electrophoresis. Method development and validation for pharmaceutical and biological applications. Electrophoresis 19:2695–2752
Rocheleau MJ (2005) Generic capillary electrophoresis conditions for chiral assay in early pharmaceutical development. Electrophoresis 26:2320–2329
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
Evans CE, Stalcup AM (2003) Comprehensive strategy for chiral separations using sulfated cyclodextrins in capillary electrophoresis. Chirality 15:709–723
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
Zhou L, Thompson R, Song S et al (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
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
Liu L, Nussbaum MA (1999) Systematic screening approach for chiral separations of basic compounds by capillary electrophoresis with modified cyclodextrins. J Pharm Biomed Anal 19:679–694
Jimidar MI, Van Ael W, Van Nyen P et al (2004) A screening strategy for the development of enantiomeric separation methods in capillary electrophoresis. Electrophoresis 25:2772–2785
Souverain S, Geiser L, Rudaz S, Veuthey JL (2006) Strategies for rapid chiral analysis by capillary electrophoresis. J Pharm Biomed Anal 40:235–241
Deeb SE, Hasemann P, Wätzig H (2008) Strategies in method development to quantify enantiomeric impurities using CE. Electrophoresis 29:3552–3562
Servais AC, 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
Sentellas S, Saurina J (2003) Chemometrics in capillary electrophoresis. Part A: method for optimization. J Sep Sci 26:875–885
Dejaegher B, Mangelings D, Vander Heyden Y (2012) Experimental design methodologies in the optimization of chiral CE or CEC separations: an overview. Methods Mol Biol 970:409–427
Orlandini S, Gotti R, Furlanetto S (2014) Multivariate optimization of capillary electrophoresis methods: a critical review. J Pharm Biomed Anal 87:290–307
Orlandini S, Pinzauti S, Furlanetto S (2013) Application of quality by design to the development of analytical separation methods. Anal Bioanal Chem 405:443–450
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
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Scriba, G.K.E., Jáč, P. (2019). Cyclodextrins as Chiral Selectors in Capillary Electrophoresis Enantioseparations. In: Scriba, G.K.E. (eds) Chiral Separations. Methods in Molecular Biology, vol 1985. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9438-0_18
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DOI: https://doi.org/10.1007/978-1-4939-9438-0_18
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