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Ketopinic acid and diisoproylideneketogulonic acid as chiral ion-pair selectors in capillary electrophoresis: Enantiomeric impurity analysis of S-timolol and 1R,2S-ephedrine
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.ORCID iD: 0000-0002-0156-8242
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
2007 (English)In: Journal of Chromatography A, ISSN 0021-9673, E-ISSN 1873-3778, Vol. 1141, no 2, 287-294 p.Article in journal (Refereed) Published
Abstract [en]

1S,4R-(+)-ketopinic acid [(+)-KPA] has been introduced as a chiral selector for the separation of pharmacologically active amines by non-aqueous capillary electrophoresis (NACE). (+)-KPA gave enantioresolution for most of the compounds previously separated by 2R,3S,4R,5S-(−)-2,3:4,6-di-O-isopropylidene-2-keto-l-gulonic acid [(−)-DIKGA], but with a reversed migration order. A complete enantioresolution (Rs = 4.2) was obtained for timolol, a compound that could not be resolved using (−)-DIKGA as the selector. Thus, (+)-KPA was evaluated for the enantiomeric purity determination of S-timolol. A method based on pre-concentration by transient isotachophoresis (tITP) provided a limit of detection (LOD) of 0.2% R-timolol in S-timolol samples. Because of the lack of enantioresolution of ephedrine when (+)-KPA was used as the selector, a method with (−)-DIKGA has been developed and validated for determination of the enantiomeric purity of the 1R,2S enantiomer. The method gave good precision and accuracy with an LOD (S/N = 3) of 0.033% for the enantiomeric impurity 1S,2R-ephedrine.

Place, publisher, year, edition, pages
2007. Vol. 1141, no 2, 287-294 p.
Keyword [en]
Diisoproylideneketogulonic acid, Enantiomeric purity, Ephedrine, Ketopinic acid, Timolol, Non-aqueous capillary electrophoresis
National Category
Pharmaceutical Sciences Analytical Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-22771DOI: 10.1016/j.chroma.2006.12.013ISI: 000244117200016PubMedID: 17187814OAI: oai:DiVA.org:uu-22771DiVA: diva2:50544
Available from: 2007-01-22 Created: 2007-01-22 Last updated: 2017-12-07

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Hedeland, YlvaPettersson, Curt

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