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Enantioseparation of Omeprazole and its Metabolite 5-Hydroxyomeprazole using Open Tubular Capillary Electrochromatography with Immobilized Avidin as Chiral Selector
Karlstad University, Faculty of Technology and Science, Department of Chemistry and Biomedical Sciences.
Karlstad University, Faculty of Technology and Science, Department of Chemistry and Biomedical Sciences.
2008 (English)In: Journal of chromatography. B, ISSN 1570-0232, E-ISSN 1873-376X, Vol. 875, no 1, 329-332 p.Article in journal (Refereed) Published
Abstract [en]

The present paper demonstrates the enantiomeric separation of omeprazole and its metabolite 5-hydroxyomeprazole performed with open tubular capillary electrochromatography (OT-CEC). The protein avidin was used as the chiral selector. Avidin was immobilized by a Schiffs base type of reaction where the protein was via glutaraldehyde covalently bonded to the amino-modified wall of a fused-silica capillary, 50 μm i.d. Both racemates were baseline resolved. Resolution was 1.9 and 2.3, respectively, using ammonium acetate buffer, pH 5.8, 5% methanol, with UV-detection. These values of resolution using OT-CEC are higher than earlier published results regarding chiral separation of omeprazole and 5-hydroxyomeprazole on packed CEC. The number of theoretical plates also indicated good separation efficiency.

Place, publisher, year, edition, pages
2008. Vol. 875, no 1, 329-332 p.
National Category
Analytical Chemistry
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:kau:diva-2028DOI: 10.1016/j.jchromb.2008.05.050OAI: oai:DiVA.org:kau-2028DiVA: diva2:5529
Available from: 2008-04-17 Created: 2008-04-17 Last updated: 2011-11-25Bibliographically approved
In thesis
1. New Techniques for Chiral Separations
Open this publication in new window or tab >>New Techniques for Chiral Separations
2008 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

Gas chromatography (GC) has been utilized for the study of enantiomer resolution of the atropisomers of PCBs, o,p´-DDD and o,p´-DDT. Different substituents and concentrations of cyclodextrin, capillary dimensions and type of stationary phase films have been investigated to achieve the resolution of as many of the atropisomers on one column as possible. The results indicated that the butyl substitution of 6-hydroxyl and the methyl substitution of 2- and 3-hydroxyl were the most promising for the enantiomeric separation. Using Capillary Electrophoresis (CE), the trimers and monomers of PM-β-CDs were compared for enantiomeric resolution, as well as comparing the cationic PMMA-β-CD with the anionic HS-β-CD. In these studies the trimer did not show an improved resolution for mepivacaine, when compared to the equimolar concentration of the monomer. The cationic CD gave increased resolution values for ibuprofen when compared to the anionic CD. A scheme for reversing enantiomeric elution order of both the basic propranolol and acidic ibuprofen is also presented, with the aim of facilitating the detection of impurities in a high sample loading. The detection of 1% of each enantiomer of propranolol, and 1% of R(-)-ibuprofen, was demonstrated, with elution prior to the tailing peak of the corresponding enantiomer. Dimethylacrylamide-coated capillaries were used in this work, and the stability of this coating was demonstrated, giving a highly reduced electroosmotic flow for up to six months. Enantiomeric baseline separations of omeprazole and 5-hydroxyomeprazole have also been achieved with both CE and Open Tubular Capillary Electrochromatography (OT-CEC) methods. With CE-UV, both a non-aqueous method (using HDMS-β-CD) and an aqueous method (using HS-β-CD) were used for enantiomeric resolution of the two racemates. Resolution of omeprazole was also achieved using CE-Electrospray Ionization-Mass Spectrometry (ESI-MS). In OT-CEC, avidin was immobilized on the inside surface of a fused silica capillary and was employed as chiral selector for the enantiomeric baseline resolution of omeprazole and 5-hydroxyomeprazole.

Place, publisher, year, edition, pages
Karlstad: Karlstads universitet, 2008. 60 p.
Series
Karlstad University Studies, ISSN 1403-8099 ; 2008:11
Keyword
analytical chemistry, chiral separation, GC, CE, CEC
National Category
Analytical Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kau:diva-1594 (URN)978-91-7063-169-6 (ISBN)
Public defence
2008-04-30, Ericssonsalen, 9C 204, Karlstads universitet, Karlstad, 10:15
Opponent
Supervisors
Available from: 2008-04-17 Created: 2008-04-17 Last updated: 2011-12-19

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Olsson, JeanetteBlomberg, Lars G.

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