Integrated experimental and theoretical approaches to investigate the molecular mechanisms of the enantioseparation of chiral anticonvulsant and antifungal compounds

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dc.authorscopusid57211413049
dc.authorscopusid57213636835
dc.authorscopusid55892526600
dc.authorscopusid6507486891
dc.authorscopusid57754335600
dc.authorscopusid6602307926
dc.authorscopusid7004088818
dc.contributor.authorGambacorta N.
dc.contributor.authorÖzdemir Z.
dc.contributor.authorDoğan İ.S.
dc.contributor.authorCiriaco F.
dc.contributor.authorZenni Y.N.
dc.contributor.authorKarakurt A.
dc.contributor.authorSaraç S.
dc.date.accessioned2024-08-04T19:59:08Z
dc.date.available2024-08-04T19:59:08Z
dc.date.issued2022
dc.departmentİnönü Üniversitesien_US
dc.description.abstractPreviously, some racemic 1-(phenyl/4-chlorophenyl)-2-(1H-triazole-1-yl)ethanol ester derivatives having a stereogenic center in their structure were synthesized and investigated for their anticonvulsant and antifungal activities. In this work, the direct enantiomeric separations of four compounds (1–4) were developed on the commercially available chiral stationary phase amylose tris(3,5-dimethyphenylcarbamate) (Chiralpak AD) in the normal phase HPLC mode. The influences of the mobile phase composition were also investigated. By mobile phase modified with n-hexane, the retention times were shorter than with methanol. The best results were obtained for all compounds (1–4) using the mobile phase of methanol/n-hexane (80:20 v/v) at a flow rate of 0.5 mL/min and the resolutions of the enantiomers were 3.38, 2.84, 1.89, and 1.53, respectively. Thus, the proposed HPLC method can facilitate further chemical and pharmacological studies on compounds 1–4 and their enantiomers. In addition, the molecular mechanism behind the possible chiral recognition was discussed based on the experimental and theoretical results of the enantiomeric separation and molecular dynamics studies. © 2022 Elsevier B.V.en_US
dc.identifier.doi10.1016/j.molstruc.2022.133905
dc.identifier.issn0022-2860
dc.identifier.scopus2-s2.0-85135953359en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.133905
dc.identifier.urihttps://hdl.handle.net/11616/90422
dc.identifier.volume1270en_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevier B.V.en_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAmylose tris(3,5-dimethyphenylcarbamate)en_US
dc.subjectArylalkylazoleen_US
dc.subjectChiralpak ADen_US
dc.subjectEnantioseparationen_US
dc.subjectMolecular modeling and dynamicsen_US
dc.titleIntegrated experimental and theoretical approaches to investigate the molecular mechanisms of the enantioseparation of chiral anticonvulsant and antifungal compoundsen_US
dc.typeArticleen_US

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