Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

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dc.contributor.authorCakmak, Resit
dc.contributor.authorErcan, Selami
dc.contributor.authorSunkur, Murat
dc.contributor.authorYilmaz, Hayrullah
dc.contributor.authorTopal, Giray
dc.date.accessioned2024-04-24T17:20:22Z
dc.date.available2024-04-24T17:20:22Z
dc.date.issued2017
dc.departmentDicle Üniversitesien_US
dc.description.abstractThis study consists of two parts. In the first part of the study; a Pirkle-type chiral stationary phase was prepared by synthesizing an aromatic amine derivative of (R)-2-amino-1-butanol as a chiral selector and binding to L-tyrosine-modified cyanogen bromide (CNBr)-activated Sepharose 4B and then, packed into the separation column. The chromatographic performance of the separation column was evaluated with racemic mandelic acid and 2-phenylpropionic acid by using phosphate buffers at three different pHs as mobile phase. In the resolution processes, the prepared solutions were loaded onto the separation column at two different concentrations and at three different pHs for each racemic organic acid, separately. Enantiomeric excess (ee%) of the eluates was determined on CHIRALPAK AD-H chiral analytical column by HPLC. The maximum ee% for mandelic acid and 2-phenylpropionic acid was determined to be 60.84 and 27.4, respectively. Separation factors (k(1)', k(2)', alpha, and Rs) were calculated for each acid. The structures of the obtained compounds were characterized using the spectroscopic methods (NMR, and elemental analysis). In the second part of the study; enantioselective interactions between the prepared CSP and the analytes have been widely studied by docking, molecular dynamics simulation and quantum mechanical computation methods. The reason of column eluation of rac-2-phenylpropionic acid with lower enantiomeric yield was explained by these techniques.en_US
dc.description.sponsorshipScientific and Technical Research Council of Turkey (TUBITAK) [110T507]; Dicle University Science and Technology Research Center (DUBTAM)en_US
dc.description.sponsorshipThe authors gratefully acknowledge to the Scientific and Technical Research Council of Turkey (TUBITAK) for financial support (Project No: 110T507). We have declared no conflict of interest. Many thanks for analysis and research support provided by Dicle University Science and Technology Research Center (DUBTAM).en_US
dc.identifier.doi10.25135/acg.oc.25.17.07.037
dc.identifier.endpage227en_US
dc.identifier.issn1307-6175
dc.identifier.issue3en_US
dc.identifier.scopus2-s2.0-85029314001
dc.identifier.scopusqualityQ3
dc.identifier.startpage216en_US
dc.identifier.urihttps://doi.org/10.25135/acg.oc.25.17.07.037
dc.identifier.urihttps://hdl.handle.net/11468/18980
dc.identifier.volume10en_US
dc.identifier.wosWOS:000411602000006
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherAcg Publicationsen_US
dc.relation.ispartofOrganic Communications
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectPirkle-Type Chiral Stationary Phaseen_US
dc.subjectEnantioseparationen_US
dc.subjectMolecular Dynamicsen_US
dc.subjectDockingen_US
dc.titleDesign, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studiesen_US
dc.titleDesign, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies
dc.typeArticleen_US

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