Chiral separation by a monofunctionalized cyclodextrin derivative: From selector to permethyl-β-cyclodextrin bonded stationary phase

Journal of Pharmaceutical and Biomedical Analysis

Volumn 51, Issue 1, 2010, Pages 84-89

  Varga, Gábor ^a   Tárkányi, Gábor ^b   Németh, Krisztina ^b   Iványi, Róbert ^c   Jicsinszky, László ^c   Toke, Orsolya ^b   Visy, Júlia ^b   Szente, Lajos ^c   Szemán, Julianna ^c   Simonyi, Miklós ^b  

^a ChiroQuest Chiral Technologies Development Ltd   (Hungary)

^b CHEMICAL RESEARCH CENTER   (Hungary)

^c CycloLab Cyclodextrin Research & Development Laboratory Ltd   (Hungary)

Author keywords

Capillary electrophoresis; HPLC; Permethylated 6 amino cyclodextrin; Solid state NMR; UPMBCD silica; Warfarin

Indexed keywords

6 MONOUREIDO 6 MONODEOXY BETA CYCLODEXTRIN; ACENOCOUMAROL; COUMARIN DERIVATIVE; CYCLODEXTRIN DERIVATIVE; PHENPROCOUMON; UNCLASSIFIED DRUG; WARFARIN;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL BOND; CHIRALITY; COMPLEX FORMATION; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SEPARATION TECHNIQUE;

BETA-CYCLODEXTRINS; CARBON ISOTOPES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARINS; MAGNETIC RESONANCE SPECTROSCOPY; NITROGEN ISOTOPES; SILICON; STEREOISOMERISM; WARFARIN;

EID: 70349333531     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2009.08.009     Document Type: Article

References (26)

1. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998) 1743-1753
2. Szemán J., Ganzler K., Salgó A., and Szejtli J. Effect of the degree of substitution of cyclodextrin derivatives on chiral separations by high-performance liquid chromatography and capillary electrophoresis. J. Chromatogr. A 728 (1996) 423-431
3. Weseloh G., Bartsch H., and König W.A. Separation of basic drugs by capillary electrophoresis using selectively modified cyclodextrins as chiral selectors. J. Microcoll. Sep. 7 (1995) 355-363
4. Arnaud S., Varesio E., Dreux M., and Veuthey J.L. Binding constant dependency of amphetamines with various commercial methylated-beta-cyclodextrins. Electrophoresis 20 (1999) 2670-2679
5. Szemán J., Roos N., and Csabai K. Ruggedness of enantiomeric separation by capillary electrophoresis and high-performance liquid chromatography with methylated cyclodextrins as chiral selectors. J. Chromatogr. A 763 (1997) 139-147
6. Schmitt U., Ertan M., and Holzgrabe U. Chiral capillary electrophoresis: facts and fiction on the reproducibility of resolution with randomly substituted cyclodextrins. Electrophoresis 25 (2004) 2801-2807
7. Vincent J.B., Sokolowski A.D., Nguyen T.V., and Vigh G. A family of single-isomer chiral resolving agents for capillary electrophoresis. 1. Heptakis(2,3-diacetyl-6-sulfato)-beta-cyclodextrin. Anal. Chem. 69 (1997) 4226-4233
8. Ivanyi R., Jicsinszky L., and Juvancz Z. Chiral separation of pyrethroic acids with single isomer permethyl monoamino beta-cyclodextrin selector. Electrophoresis 22 (2001) 3232-3236
9. West B.D., Preis S., Schroeder C.H., and Link K.P. Studies on the 4-hydroxycoumarins. XV1I. The resolution and absolute configuration of warfarin. J. Am. Chem. Soc. 83 (1961) 2676-2679
10. Jicsinszky L., and Iványi R. Catalytic transfer hydrogenation of sugar derivatives. Carbohydr. Polym. 45 (2001) 139-145
11. Fanali S. Controlling enantioselectivity in chiral capillary electrophoresis with inclusion-complexation. J. Chromatogr. A 792 (1997) 227-267
12. Bellini M.S., Deyl Z., Manetto G., and Kohlicková M. Determination of apparent binding constants of drugs by capillary electrophoresis using β-cyclodextrin as ligand and three different linear plotting methods. J. Chromatogr. A 924 (2001) 483-491
13. Jakubetz H., Juza M., and Schurig V. Electrokinetic chromatography employing an anionic and a cationic beta-cyclodextrin derivative. Electrophoresis 18 (1997) 897-904
14. Perrin C., Fabre H., Maftouh M., Massart D.L., and Heyden Y.V. Robustness testing of chiral separations by capillary electrophoresis using highly-sulfated cyclodextrins. J. Chromatogr. A 1007 (2003) 165-177
15. Chen J., Ohnmacht C.M., and Hage D.S. Characterization of drug interactions with soluble beta-cyclodextrin by high-performance affinity chromatography. J. Chromatogr. A 1033 (2004) 115-126
16. Schurig V., and Mayer S. Separation of enantiomers by open capillary electrochromatography on polysiloxane-bonded permethyl-beta-cyclodextrin. J. Biochem. Biophys. Methods 48 (2001) 117-141
17. Dittmann H., Scharwachter K., and Konig W.A. Synthesis and silica-based immobilization of mono-functionalized cyclomaltoheptaose derivatives for enantioselective HPLC. Carbohydr. Res. 324 (2000) 75-96
18. Ng S.C., Ong T.T., Fu P., and Ching C.B. Enantiomer separation of flavour and fragrance compounds by liquid chromatography using novel urea-covalent bonded methylated beta-cyclodextrins on silica. J. Chromatogr. A 968 (2002) 31-40
19. Poon Y., Muderawan I., and Ng S. Synthesis and application of mono-2(A)-azido-2(A)-deoxyperphenylcarbamoylated beta-cyclodextrin and mono-2(A)-azido-2(A)-deoxyperacetylated beta-cyclodextrin as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. A 1101 (2006) 185-197
20. Lai X.H., and Ng S.C. Enantioseparation on mono(6A-N-allylamino-6A-deoxy) permethylated β-cyclodextrin covalently bonded silica gel. J. Chromatogr. A 1059 (2004) 53-59
21. Muderawan I.W., Ong T.T., and Ng S.C. Urea bonded cyclodextrin derivatives onto silica for chiral HPLC. J. Sep. Sci. 29 (2006) 1849-1871
22. Andrew E.R. The narrowing of NMR spectra of solids by high-speed specimen rotation and the resolution of chemical shift and spin multiplet structures for solids. Prog. NMR Spectrosc. 8 (1972) 1-39
23. Pines A., Gibby M.G., and Waugh J.S. Proton enhanced NMR of dilute spins in solids. J. Chem. Phys. 59 (1973) 569-590
24. Albert K.E. Bayer Characterization of bonded phases by solid-state NMR-spectroscopy. J. Chromatogr. 544 (1991) 345-370
25. Chuang I.S., and Maciel G.E. A detailed model of local structure and silanol hydrogen bonding of silica gel surfaces. J. Phys. Chem. B 101 (1997) 3052-3064
26. Pfleiderer B., Albert K., and Bayer E. Investigations by Si-29 cross-polarization magic angle spinning NMR-spectroscopy of reaction pathways of silica-gel polyfunctional modification. J. Chromatogr. 506 (1990) 343-355