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Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis by the cationic cyclodextrin derivative 2-hydroxypropyltrimethyl-ammonium-β-cyclodextrin and by neutral β-cyclodextrin derivatives at alkaline pH

2002; Wiley; Volume: 25; Issue: 15-17 Linguagem: Inglês

10.1002/1615-9314(20021101)25

1615-9314

Falko Süß, Wolfgang Poppitz, Gerhard K. E. Scriba,

Protein purification and stability

Journal of Separation ScienceVolume 25, Issue 15-17 p. 1147-1154 Research Article Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis by the cationic cyclodextrin derivative 2-hydroxypropyltrimethyl-ammonium-β-cyclodextrin and by neutral β-cyclodextrin derivatives at alkaline pH Falko Süß, Falko Süß University of Jena, School of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Philosophenweg 14, 07743 Jena, Germany; Fax: +49 3641 949802Search for more papers by this authorWolfgang Poppitz, Wolfgang Poppitz University of Jena, Department of Inorganic and Analytical Chemistry, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorGerhard K. E. Scriba, Gerhard K. E. Scriba [email protected] Search for more papers by this author Falko Süß, Falko Süß University of Jena, School of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Philosophenweg 14, 07743 Jena, Germany; Fax: +49 3641 949802Search for more papers by this authorWolfgang Poppitz, Wolfgang Poppitz University of Jena, Department of Inorganic and Analytical Chemistry, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorGerhard K. E. Scriba, Gerhard K. E. Scriba [email protected] Search for more papers by this author First published: 27 November 2002 https://doi.org/10.1002/1615-9314(20021101)25:15/17 3.0.CO;2-CCitations: 27AboutPDF 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 The enantioseparation of dipeptides and tripeptides by the cationic CD derivative 2-Hydroxy-3-trimethylammoniumpropyl-β-cyclodextrin (TMA-β-CD) was studied under acidic and alkaline conditions. Enantioresolutions could be achieved at pH 3.5 when the peptides were partially positively charged, at pH 5.3 close to the isoelectric point of the peptides when the compounds are uncharged, and at pH 9.5 where the peptides exist as anions. Although not as effective as under acidic run conditions, native β-CD and neutral CD derivatives were able to resolve the enantiomers of several peptides at pH 9.5. Analysis of the complexation constants and the mobilities of the analyte-CD complexes at pH 9.5 in the presence of TMA-β-CD and β-CD revealed identical chiral recognition of both CDs towards Ala-Phe, Ala-Tyr, and Asp-PheOMe. Despite identical enantiomer migration order compared to the other peptides, TMA-β-CD displayed opposite chiral recognition towards the enantiomers of Ala-Trp. 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