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Capillary electrophoresis chiral separation of basic pharmaceutical enantiomers with different charges using sulfated ?-cyclodextrin

1999; Wiley; Volume: 11; Issue: 1 Linguagem: Inglês

10.1002/(sici)1520-667x(1999)11

1520-667X

Fang Wang, Morteza G. Khaledi,

Innovative Microfluidic and Catalytic Techniques Innovation

Journal of Microcolumn SeparationsVolume 11, Issue 1 p. 11-21 Research Article Capillary electrophoresis chiral separation of basic pharmaceutical enantiomers with different charges using sulfated β-cyclodextrin Fang Wang, Fang Wang Department of Chemistry, Box 8204, North Carolina State University, Raleigh, NC 27695-8204, USASearch for more papers by this authorMorteza G. Khaledi, Corresponding Author Morteza G. Khaledi Department of Chemistry, Box 8204, North Carolina State University, Raleigh, NC 27695-8204, USADepartment of Chemistry, Box 8204, North Carolina State University, Raleigh, NC 27695-8204, USASearch for more papers by this author Fang Wang, Fang Wang Department of Chemistry, Box 8204, North Carolina State University, Raleigh, NC 27695-8204, USASearch for more papers by this authorMorteza G. Khaledi, Corresponding Author Morteza G. Khaledi Department of Chemistry, Box 8204, North Carolina State University, Raleigh, NC 27695-8204, USADepartment of Chemistry, Box 8204, North Carolina State University, Raleigh, NC 27695-8204, USASearch for more papers by this author First published: 07 January 1999 https://doi.org/10.1002/(SICI)1520-667X(1999)11:1 3.0.CO;2-PCitations: 28AboutPDF 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 onFacebookTwitterLinked InRedditWechat Abstract A negatively charged cyclodextrin, sulfated β-cyclodextrin [β-CD-(SO4−)4], was used as a chiral selector for capillary electrophoresis separations of basic pharmaceutical enantiomers. The charges of the basic enantiomers were controlled by adjusting the buffer pH. At pH 2.5, basic compounds are positively charged and interact stronger with the negatively charged CD than with neutral CDs, owing to the extra electrostatic interaction. This additional interaction is very useful for chiral separations of the enantiomers that interact weakly with the neutral CDs. For example, chiral separations of acebutolol, metanephrine, normetanephrine, nafronyl, labetalol, and nadolol were achieved at this pH. For labetalol and nadolol that have two chiral centers, three of the four isomers were separated. The capillary surface was dynamically coated with poly(vinyl alcohol) (PVA) to reduce the possible interactions between solutes and the capillary wall, to improve efficiency and reduce the electroosmotic flow (EOF) for enhancing resolution. PVA reduced the interactions between the analytes and the chiral selector; nevertheless, peak tailing was observed owing to the electrodispersion for the compounds that interact too strongly with the anionic CD. At pH 11.6, most of the basic test compounds (except those having phenol groups) are neutral and have weaker interactions with the negatively charged CD. The separation efficiency increased dramatically for all analytes at higher pH owing to the absence of electrodispersion. The existence of the neutral PVA polymer in the buffer solution increased the solubility of the neutral hydrophobic amines and reduced the solute–CD complexation. Chiral separations of a large number of compounds were achieved at a single concentration of the charged cyclodextrin. ©1999 John Wiley & Sons, Inc. J Micro Sep 11: 11–21, 1999 Citing Literature Volume11, Issue11999Pages 11-21 RelatedInformation