Artigo Revisado por pares

Comparative enantioseparations with native β-cyclodextrin and heptakis-(2-O-methyl- 3,6-di-O-sulfo)-β-cyclodextrin in capillary electrophoresis

2002; Wiley; Volume: 23; Issue: 17 Linguagem: Inglês

10.1002/1522-2683(200209)23

ISSN

1522-2683

Autores

Bezhan Chankvetadze, Naira Burjanadze, Dawn Maynard, Klaus Bergander, Dieter Bergenthal, Gottfried Blaschke,

Tópico(s)

Innovative Microfluidic and Catalytic Techniques Innovation

Resumo

ELECTROPHORESISVolume 23, Issue 17 p. 3027-3034 Research Article Comparative enantioseparations with native β-cyclodextrin and heptakis-(2-O-methyl- 3,6-di-O-sulfo)-β-cyclodextrin in capillary electrophoresis Bezhan Chankvetadze, Corresponding Author Bezhan Chankvetadze [email protected] Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, Germany Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, GeorgiaInstitute of Pharmaceutical and Medicinal Chemistry, University of Münster, Hittorfstr. 58–62, D-48149 Münster, Germany Fax: +49-251-8332144===Search for more papers by this authorNaira Burjanadze, Naira Burjanadze Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, GermanySearch for more papers by this authorDawn M. Maynard, Dawn M. Maynard Laboratory of Neurotoxicology, National Institute of Mental Health, Bethesda, MD, USASearch for more papers by this authorKlaus Bergander, Klaus Bergander Institute of Organic Chemistry, University of Münster, Münster, GermanySearch for more papers by this authorDieter Bergenthal, Dieter Bergenthal Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, GermanySearch for more papers by this authorGottfried Blaschke, Gottfried Blaschke Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, GermanySearch for more papers by this author Bezhan Chankvetadze, Corresponding Author Bezhan Chankvetadze [email protected] Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, Germany Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, GeorgiaInstitute of Pharmaceutical and Medicinal Chemistry, University of Münster, Hittorfstr. 58–62, D-48149 Münster, Germany Fax: +49-251-8332144===Search for more papers by this authorNaira Burjanadze, Naira Burjanadze Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, GermanySearch for more papers by this authorDawn M. Maynard, Dawn M. Maynard Laboratory of Neurotoxicology, National Institute of Mental Health, Bethesda, MD, USASearch for more papers by this authorKlaus Bergander, Klaus Bergander Institute of Organic Chemistry, University of Münster, Münster, GermanySearch for more papers by this authorDieter Bergenthal, Dieter Bergenthal Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, GermanySearch for more papers by this authorGottfried Blaschke, Gottfried Blaschke Institute of Pharmaceutical and Medicinal Chemistry, University of Münster, Münster, GermanySearch for more papers by this author First published: 02 September 2002 https://doi.org/10.1002/1522-2683(200209)23:17 3.0.CO;2-VCitations: 59AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Twenty-three cationic chiral analytes were resolved in capillary electrophoresis using native β-cyclodextrin and single isomer heptakis-(2-O-methyl-3,6-di-O-sulfo)-β-cyclodextrin as chiral selectors. For 12 of 16 chiral analytes resolved with both chiral selectors the enantiomer migration order was opposite. In selected cases the structure of cyclodextrin-analyte complexes in aqueous solution was investigated using one-dimensional transverse rotating frame nuclear Overhauser and exchange spectroscopy. It was found that in contrast to mainly inclusion-type complexes between chiral analytes and β-cyclodextrin, external complexes are formed between the chiral analytes and structurally crowded, highly charged heptakis-(2-O-methyl-3,6-di-O-sulfo)-β-cyclodextrin. REFERENCES 1 Chankvetadze, B., Endresz, G., Blaschke, G., Chem. Soc. Rev 1996, 25, 141–153. 2 Terabe, S., Trends Anal. Chem. 1989, 8, 129–134. 3 Vigh, G., Sokolowski, A. D., Electrophoresis 1997, 18, 2305–2310. 4 Chankvetadze, B., J. Chromatogr. A 1997, 792, 269–295. 5 Chankvetadze, B., Blaschke, G., J. Chromatogr. A 2001, 906, 309–363. 6 Fanali, S., J. Chromatogr. A 1997, 792, 227–267. 7 Chankvetadze, B., Endresz, G., Blaschke, G., Electrophoresis 1994, 15, 804–807. 8 Schmitt, T., Engelhardt, H., Chromatographia 1993, 37, 475–481. 9 Terabe, S., Ozaki, K., Otsuka, K., Ando, T., J. Chromatogr 1985, 332, 211–217. 10 Nardi, A., Eliseev, A., Boček, P., Fanali, S., J. Chromatogr 1993, 638, 247–253. 11 Vincent, J. B., Sokolowski, A. D., Nguyen, T. V., Vigh, G., Anal. Chem 1997, 69, 4226–4233. 12 Cai, H., Nguyen, T. V., Vigh, G., Anal. Chem. 1998, 70, 580–589. 13 Vincent, J. B., Maynard, D. K., Nguyen, T. V., Vigh, G., Anal. Chem 1997, 69, 4419–4428. 14 Maynard, D. K., Vigh, G., Electrophoresis 2001, 22, 3152–3162. 15 Maynard, D. K., Vigh, G., Carbohydr. Res 2000, 328, 277–285. 16 Chankvetadze, B., Lomsadze, K., Bergenthal, D., Breitkreutz, J., Bergander, K., Blaschke, G., Electrophoresis 2001, 22, 3178–3184. 17 Chankvetadze, B., Burjanadze, N., Crommen, J., Blaschke, G., Chromatographia 2001, 53, S296–S301. 18 Chankvetadze, B., Kartozia, I., Burjanadze, N., Bergenthal, D., Bergander, K., Luftmann, H., Blaschke, G., Chromatographia 2001, 53, S290–S295. 19 Hwang, T.-L., Shaka, A. J., J. Magn. Reson., Ser. B 1993, 102, 155–165. 20 Hwang, T.-L., Kadkhodaei, M., Mohebbi, A., Shaka, A. J., Magn. Reson. Chem. 1992, 30, S24–S34. 21 Green, H., Freeman, R., J. Magn. Reson. 1991, 93, 93–141. 22 Radler, S., Wermeille, M., Blaschke, G., Arzneim. Forsch./Drug Res 1995, 45, 1086–1092. 23 Carole, F. I., Blackwell, J. T., J. Med. Chem 1974, 17, 210–219. 24 Hudyma, T. W., Holmes, S. W., Hooper, I. R., German Offen, 2, 062, 620, 1970. 25 Blaschke, G., Doebber, P., German Offen DE 3, 723, 684, 1989. 26 Chankvetadze, B., Fillet, M., Burjanadze, N., Bergenthal, D., Bergander, K., Luftmann, H., Crommen, J., Blaschke, G., Enantiomer 2000, 5, 313–322. 27 Chankvetadze, B., Pintore, G., Burjanadze, N., Bergenthal, D., Strickmann, D., Cerri, R., Blaschke, G., Electrophoresis 1998, 19, 2101–2108. 28 Chankvetadze, B., Burjanadze, N., Pintore, G., Bergenthal, D., Bergander, K., Mühlenbrock, C., Breitkreutz, J., Blaschke, G., J. Chromatogr. A 2000, 875, 471–484. 29 Chankvetadze, B., Pintore, G., Burjanadze, N., Bergenthal, D., Bergander, K., Breitkreutz, J., Mühlenbrock, C., Blaschke, G., J. Chromatogr. A 2000, 875, 455–469. 30 Chankvetadze, B., Burjanadze, N., Pintore, G., Strickmann, D., Bergenthal, D., Blaschke, G., Chirality 1999, 11, 635–644. 31 Armstrong, D. W., Stalcup, A. M., Hilton, M. L., Dunkan, J.-D., Foulkner, J. R. Jr., Chang, S.-C., Anal. Chem 1990, 62, 1610–1615. Citing Literature Volume23, Issue17Special Issue: Paper Symposium CE AND CEC INNOVATIONSNo. 17 September 2002Pages 3027-3034 ReferencesRelatedInformation

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