Chiral HPLC Separation on Derivatized Cyclofructan Versus Cyclodextrin Stationary Phases

Analytical Letters

Volumn 45, Issue 16, 2012, Pages 2344-2358

  Vozka, Jiří ^a   Kalíková, Květa ^a   Janečková, Lucie ^a,b   Armstrong, Daniel W ^c   Tesařová, Eva ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b Zentiva AS Prague ^*  (Czech Republic)

^c UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

Author keywords

Chiral separation; Cyclodextrin; Cyclofructan; HPLC

Indexed keywords

EID: 84868091794     PISSN: 00032719     EISSN: 1532236X     Source Type: Journal    
DOI: 10.1080/00032719.2012.686128     Document Type: Article

References (28)

1. Aranyi, A., I. Ilisz, Z. Pataj, I. Szatmári, F. Fülöp, D. W. Armstrong, and A. Péter. 2011. High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase. Chirality 23: 549-556.
2. Armstrong, D. W., and W. DeMond. 1984. Cyclodextrin bonded phases for the liquid chromatographic separation of optical, geometrical, and structural isomers. J. Chromatogr. Sci. 22: 411-415.
3. Armstrong, D. W., A. M. Stalcup, M. L. Hilton, J. D. Duncan, J. R. Faulkner, and S. Chang. 1990. Derivatized cyclodextrins for normal-phase liquid chromatographic separation of enantiomers. Anal. Chem.62: 1610-1615.
4. Beesly, T. E., and R. P. W. Scott. 1998. Chiral Chromatography. Chichester, UK: Wiley and Sons.
5. Cavazzini, A., L. Pasti, A. Massi, N. Marchetti, and F. Dondi. 2011. Recent applications in chiral high performance liquid chromatography: A review. Anal. Chim. Acta 706: 205-222.
6. Han, S. M. 1997. Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins. Biomed. Chromatogr. 11: 259-271.
7. Han, X., A. Berthod, K. Wang, K. Huang, and D. W. Armstrong. 2007. Super/subcritical fluid chromatography separation with four synthetic polymeric chiral stationary phases. Chromatographia 65: 381-400.
8. Immel, S., G. E. Schmitt, and F. W. Lichtenthaler. 1998. Cyclofructins with six to ten β-(2,1) linked fructofuranose units: Geometries, electrostatic profiles, lipophilicity patterns, and potential for inclusion complexation. Carbohydr. Res. 313: 91-105.
9. Janečková, L., K. Kalíková, J. Vozka, D. W. Armstrong, Z. Bosáková, and E. Tesařová. 2011. Characterization of cyclofructan-based chiral stationary phases by linear free energy relationship. J. Sep. Sci. 34: 2639-2644.
10. Kalíková, K., L. Janečková, D. W. Armstrong, and E. Tesařová. 2011. Characterization of new R-naphthylethyl cyclofructan 6 chiral stationary phase and its comparison with R-naphthylethyl β-cyclodextrin-based column. J. Chromatogr. A 1218: 1393-1398.
11. Kalíková, K., M. Riesová, and E. Tesařová. 2011. Recent chiral selectors for separation in HPLC and CE. Centr. Eur. J. Chem. DOI: 10.2478/s11532-011-0142-3.
12. Kočovský, P., Š. Vyskočil, and M. Smrčina. 2003. Non-symmetrically substituted 1,1'-binaphthyls in enantioselective catalysis. Chem. Rev. 103: 3213-3245.
13. Lämmerhofer, M. 2010. Chiral recognition by enantioselective liquid chromatography: Mechanisms and modern chiral stationary phases. J. Chromatogr. A 1217: 814-856.
14. Loukotková, L., M. Rambousková, Z. Bosáková, and E. Tesařová. 2008. Cellulose tris(3,5-dimethylphenylcarbamate)-based chiral stationary phases as effective tools for enantioselective HPLC separation of structurally different disubstituted binaphthyls. Chirality 20: 900-909.
15. Loukotková, L., E. Tesařová, Z. Bosáková, P. Repko, and D. W. Armstrong. 2010. Comparison of HPLC enantioseparation of substituted binaphthyls on CD-, polysaccharide- and synthetic polymer-based chiral stationary phases. J. Sep. Sci. 33: 1244-1254.
16. Muderawan, W., T. T. Ong, and S. Ch. Ng. 2006. Urea bonded cyclodextrin derivatives onto silica for chiral HPLC. J. Sep. Sci. 29: 1849-1871.
17. Padivitage, N. L. T., and D. W. Armstrong. 2011. Sulfonated cyclofructan 6 based stationary phase for hydrophilic interaction chromatography. J. Sep. Sci. 34: 1636-1647.
18. Qiu, H., X. Liang, M. Sun, and S. Jiang. 2011. Development of silica-based stationary phases for high-performance liquid chromatography. Anal. Bioanal. Chem. 399: 3307-3322.
19. Qiu, H., L. Loukotková, P. Sun, E. Tesařová, Z. Bosáková, and D. W. Armstrong. 2011. Cyclofructan 6 based stationary phases for hydrophilic interaction liquid chromatography. J. Chromatogr. A 1218: 270-279.
20. Remsburg, J. W., D. W. Armstrong, A. Péter, and G. Tóth. 2008. LC enantiomeric separation of unusual amino acids using cyclodextrin-based stationary phases. J. Liq. Chromatogr. R. T. 31: 219-230.
21. Sawada, M., T. Tanaka, Y. Takai, T. Hanafusa, T. Taniguchi, M. Kawamura, and T. Uchiyama. 1991. The crystal structure of cycloinulohexaose produced from inulin by cycloinulo-oligosaccharide fructanotransferase. Carbohydr. Res. 217: 7-17.
22. Sovák, M., A. L. Seligson, R. Kučerová, M. Bienová, M. Hajdúch, and M. Buček. 2002. Fluridil, a rationally designed topical agent for androgenetic alopecia: First clinical experience. Dermatol. Surg. 28: 678-685.
23. Sun, P., and D. W. Armstrong. 2010. Effective enantiomeric separations of racemic primary amines by the isopropyl carbamate-cyclofructan6 chiral stationary phase. J. Chromatogr. A1217: 4904-4918.
24. Sun, P., C. Wang, Z. S. Breitbach, Y. Zhang, and D. W. Armstrong. 2009. Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans. Anal. Chem. 81: 10215-10226.
25. Sun, P., C. Wang, N. L. T. Padivitage, Z. S. Nanayakkara, S. Perera, H. X. Qiu, Y. Zhang, and D. W. Armstrong. 2011. Evaluation of aromatic-derivatized cyclofructans 6 and 7 as HPLC chiral selectors. Analyst 136: 787-800.
26. Tang, W., and S. Ch. Ng. 2008. Monosubstituted positively charged cyclodextrins: Synthesis and applications in chiral separation. J. Sep. Sci. 31: 3246-3256.
27. Vyskočil, Š., L. Meca, L. Tišlerová, I. Císařová, M. Polášek, S. R. Harutyunyan, et al. 2002. 2,8′-disubstituted-1,1′-binaphthyls: A new pattern in chiral ligands. Chem.-Eur. J. 8: 4633-4648.
28. Zhou, Z., X. Li, X. Chen, and X. Hao. 2010. Synthesis of ionic liquids functionalized β-cyclodextrin-bonded chiral stationary phases and their applications in high-performance liquid chromatogramy. Anal. Chim. Acta 678: 208-214.