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New Techniques for Chiral Separations
Karlstads universitet, Fakulteten för teknik- och naturvetenskap, Avdelningen för kemi och biomedicinsk vetenskap.
2008 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Karlstad: Karlstads universitet, 2008. , s. 60
Serie
Karlstad University Studies, ISSN 1403-8099 ; 2008:11
Nyckelord [en]
analytical chemistry, chiral separation, GC, CE, CEC
Nationell ämneskategori
Analytisk kemi
Forskningsämne
Kemi
Identifikatorer
URN: urn:nbn:se:kau:diva-1594ISBN: 978-91-7063-169-6 (tryckt)OAI: oai:DiVA.org:kau-1594DiVA, id: diva2:5530
Disputation
2008-04-30, Ericssonsalen, 9C 204, Karlstads universitet, Karlstad, 10:15
Opponent
Handledare
Tillgänglig från: 2008-04-17 Skapad: 2008-04-17 Senast uppdaterad: 2011-12-19
Delarbeten
1. Gas Chromatographic Enantiomer Separation of Atropisomeric PCBs Using Modified Cyclodextrins as Chiral Phases
Öppna denna publikation i ny flik eller fönster >>Gas Chromatographic Enantiomer Separation of Atropisomeric PCBs Using Modified Cyclodextrins as Chiral Phases
Visa övriga...
2000 (Engelska)Ingår i: HRC Journal of High Resolution Chromatography, ISSN 0935-6304, E-ISSN 1521-4168, Vol. 23, nr 11, s. 619-627Artikel i tidskrift (Refereegranskat) Published
Identifikatorer
urn:nbn:se:kau:diva-2024 (URN)10.1002/1521-4168(20001101)23:11<619::AID-JHRC619>3.0.CO;2-2 (DOI)
Tillgänglig från: 2008-04-17 Skapad: 2008-04-17 Senast uppdaterad: 2017-12-07Bibliografiskt granskad
2. Illustration of a Simple and Versatile Scheme for Reversing Enantiomeric Elution Order and Facilitating Enantiomeric Impurity Determination in Capillary Electrophoresis
Öppna denna publikation i ny flik eller fönster >>Illustration of a Simple and Versatile Scheme for Reversing Enantiomeric Elution Order and Facilitating Enantiomeric Impurity Determination in Capillary Electrophoresis
2002 (Engelska)Ingår i: Electrophoresis, ISSN 0173-0835, E-ISSN 1522-2683, Vol. 23, nr 17, s. 3013-3019Artikel i tidskrift (Refereegranskat) Published
Identifikatorer
urn:nbn:se:kau:diva-2025 (URN)10.1002/1522-2683(200209)23:17<3013::AID-ELPS3013>3.0.CO;2-K (DOI)
Tillgänglig från: 2008-04-17 Skapad: 2008-04-17 Senast uppdaterad: 2017-12-07Bibliografiskt granskad
3. Enantiomeric Separation of Omeprazole and its Metabolite 5-Hydroxymeprazole Using Non-aqueous Capillary Electrophoresis
Öppna denna publikation i ny flik eller fönster >>Enantiomeric Separation of Omeprazole and its Metabolite 5-Hydroxymeprazole Using Non-aqueous Capillary Electrophoresis
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2006 (Engelska)Ingår i: Journal of Chromatography A, ISSN 0021-9673, E-ISSN 1873-3778, Vol. 1129, nr 2, s. 291-295Artikel i tidskrift (Refereegranskat) Published
Identifikatorer
urn:nbn:se:kau:diva-2026 (URN)10.1016/j.chroma.2006.07.001 (DOI)
Tillgänglig från: 2008-04-17 Skapad: 2008-04-17 Senast uppdaterad: 2017-12-07Bibliografiskt granskad
4. Enantiomeric Separation of Omeperazole Enantiomers by Aqueous CE Using UV and MS Detection
Öppna denna publikation i ny flik eller fönster >>Enantiomeric Separation of Omeperazole Enantiomers by Aqueous CE Using UV and MS Detection
2007 (Engelska)Ingår i: Chromatographia, ISSN 0009-5893, E-ISSN 1612-1112, Vol. 66, nr 5-6, s. 421-425Artikel i tidskrift (Refereegranskat) Published
Identifikatorer
urn:nbn:se:kau:diva-2027 (URN)10.1365/s10337-007-0317-4 (DOI)
Tillgänglig från: 2008-04-17 Skapad: 2008-04-17 Senast uppdaterad: 2017-12-07Bibliografiskt granskad
5. Enantioseparation of Omeprazole and its Metabolite 5-Hydroxyomeprazole using Open Tubular Capillary Electrochromatography with Immobilized Avidin as Chiral Selector
Öppna denna publikation i ny flik eller fönster >>Enantioseparation of Omeprazole and its Metabolite 5-Hydroxyomeprazole using Open Tubular Capillary Electrochromatography with Immobilized Avidin as Chiral Selector
2008 (Engelska)Ingår i: Journal of chromatography. B, ISSN 1570-0232, E-ISSN 1873-376X, Vol. 875, nr 1, s. 329-332Artikel i tidskrift (Refereegranskat) 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.

Nationell ämneskategori
Analytisk kemi
Forskningsämne
Kemi
Identifikatorer
urn:nbn:se:kau:diva-2028 (URN)10.1016/j.jchromb.2008.05.050 (DOI)
Tillgänglig från: 2008-04-17 Skapad: 2008-04-17 Senast uppdaterad: 2017-12-07Bibliografiskt granskad

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