Enantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C1 symmetry: experimental and theoretical approaches

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dc.contributor.authorKocakaya, Safak Ozhan
dc.contributor.authorTurgut, Yilmaz
dc.contributor.authorPirinccioglu, Necmettin
dc.date.accessioned2024-04-24T16:01:59Z
dc.date.available2024-04-24T16:01:59Z
dc.date.issued2015
dc.departmentDicle Üniversitesien_US
dc.description.abstractThe work involves an experimental (H-1 NMR) and theoretical (MD, MM-PBSA and DFT) investigation of the molecular recognition and discrimination properties of a chiral aza-15-crown-5 against methyl esters of alanine, phenylalanine and valine hydrochloride salts. The results indicate that the receptor binds enantiomers with moderate binding constants (88-1,389 M-1), with phenylalanine being more discriminated. The difference in experimental binding free energies (Delta G(R) - Delta G(S)) for alanine, phenylalanine and valine enantiomers were calculated as -0.36, -1.58 and 0.80 kcal mol(-1), respectively. The differences in theoretical binding energies were calculated by MM-PBSA (Delta E-PB(R) - Delta E-PB(S)=) as -0.30, -1.45 and 0.88, by B3LYP/6-31+G(d) as -1.17, -0.84 and 0.74 and by M06-2X/6-31+G(d) as -1.40, -3.26 and 1.66 kcal mol(-1). The data obtained give valuable information regarding the molecular recognition mode of the organoammonium complexes of chiral aza-crown ether with C-1 symmetry, which may be relevant to biological systems.en_US
dc.description.sponsorshipDicle University Research Council [DUAPK-02-FF-20, DUBAP-05-FF-31, DUBAP-05-FF-32]en_US
dc.description.sponsorshipWe are grateful to Dicle University Research Council for financial support (DUAPK-02-FF-20, DUBAP-05-FF-31 and DUBAP-05-FF-32), Dr. Selami Ercan for Gaussian 09 facilities, The Scientific and Technological Research Council of Turkey (TUBITAK) for TR-GRID facilities and Professor D. Case for a waiver license of AMBER.en_US
dc.identifier.doi10.1007/s00894-015-2604-6
dc.identifier.issn1610-2940
dc.identifier.issn0948-5023
dc.identifier.issue3en_US
dc.identifier.pmid25701087
dc.identifier.scopus2-s2.0-84923347884
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1007/s00894-015-2604-6
dc.identifier.urihttps://hdl.handle.net/11468/14549
dc.identifier.volume21en_US
dc.identifier.wosWOS:000349970900019
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoenen_US
dc.publisherSpringeren_US
dc.relation.ispartofJournal of Molecular Modeling
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectEnantiomeric Discriminationen_US
dc.subjectChiral Aza-Crown Etheren_US
dc.subjectMolecular Recognitionen_US
dc.subjectAmino Acid Ester Salten_US
dc.subjectH-1 Nmr Titrationen_US
dc.subjectComputational Calculationen_US
dc.subjectMolecular Dynamicsen_US
dc.subjectMm-Pbsaen_US
dc.subjectDften_US
dc.titleEnantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C1 symmetry: experimental and theoretical approachesen_US
dc.titleEnantiomeric discrimination of chiral organic salts by chiral aza-15-crown-5 ether with C1 symmetry: experimental and theoretical approaches
dc.typeArticleen_US

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