Enantiomeric recognition of amino acid ester salts by ?-cyclodextrin derivatives: an experimental and computational study

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dc.contributor.authorRezanka, Michal
dc.contributor.authorStibor, Ivan
dc.contributor.authorAzizoglu, Murat
dc.contributor.authorTurgut, Yilmaz
dc.contributor.authorPirinccioglu, Necmettin
dc.date.accessioned2024-04-24T17:24:09Z
dc.date.available2024-04-24T17:24:09Z
dc.date.issued2016
dc.departmentDicle Üniversitesien_US
dc.description.abstractbeta-cyclodextrin derivatives bearing benzoyl (beta-CD-1) and naphthoyl beta-CD-2) moieties have been synthesized from salicylic acid and 3-hydroxy-2-naphthoic acid by a convenient method in 60% and 58% yields, respectively, and were tested for enantiomeric recognition of amino acid ester derivatives. Their ability to discriminate between various L-/D-amino acid methyl ester hydrochloride salts was examined using the H-1 NMR titration method in DMSO-d(6) at 25 degrees C. beta-CD- 2 produced a fairly good discrimination of tryptophan ester salts with a binding constant of 4041 M-1 for L-salt compared with 2864 M-1 for D-salt, which corresponds to a difference of 0.21 kcal mol(-1) in binding free energies. The binding free energies obtained from molecular dynamic calculation by MM/PB(GB) SA are consistent with those obtained from the experimental results.en_US
dc.description.sponsorshipproject Development of research teams of R&D projects at the Technical University of Liberec [CZ.1.07/2.3.00/30.0024]; Ministry of Education, Youth and Sports [LO1201]; OPR&DI project Centre for Nanomaterials, Advanced Technologies and Innovation [CZ.1.05/2.1.00/01.0005]en_US
dc.description.sponsorshipThis work was supported from project CZ.1.07/2.3.00/30.0024 Development of research teams of R&D projects at the Technical University of Liberec, project LO1201 of the Ministry of Education, Youth and Sports in the framework of the targeted support of the National Programme for Sustainability I and the OPR&DI project Centre for Nanomaterials, Advanced Technologies and Innovation CZ.1.05/2.1.00/01.0005. We also give special thanks to Professor D. Case for providing us with a waiver license for AMBER and The Scientific and Technological Research Council of Turkey (TUBITAK) for computer facilities.en_US
dc.identifier.doi10.3998/ark.5550190.p009.657
dc.identifier.endpage267en_US
dc.identifier.issn1551-7004
dc.identifier.issn1551-7012
dc.identifier.scopus2-s2.0-84991396117
dc.identifier.scopusqualityQ4
dc.identifier.startpage249en_US
dc.identifier.urihttps://doi.org/10.3998/ark.5550190.p009.657
dc.identifier.urihttps://hdl.handle.net/11468/19455
dc.identifier.wosWOS:000385801100017
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherArkat Usa Incen_US
dc.relation.ispartofArkivoc
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectBeta-Cyclodextrin Derivativesen_US
dc.subjectEnantiomeric Discriminationen_US
dc.subjectH-1 Nmr Titrationen_US
dc.subjectMolecular Dynamic Calculationsen_US
dc.subjectMm-Pb(Gb)Saen_US
dc.titleEnantiomeric recognition of amino acid ester salts by ?-cyclodextrin derivatives: an experimental and computational studyen_US
dc.titleEnantiomeric recognition of amino acid ester salts by ?-cyclodextrin derivatives: an experimental and computational study
dc.typeArticleen_US

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