Pyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulations

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dc.contributor.authorTurgut, Yilmaz
dc.contributor.authorKocakaya, Safak Ozhan
dc.date.accessioned2024-04-24T16:18:27Z
dc.date.available2024-04-24T16:18:27Z
dc.date.issued2010
dc.departmentDicle Üniversitesien_US
dc.description.abstractTwo novel C-2-symmetric optically active pyridine-15-crown-5 type ligands containing lipophilic chains at the stereogenic centres, macrocycles 5 and 6, were prepared from (S)-1,2-propanediol and (S)-3-aryloxy-1,2-propanediol for the enantiomeric recognition of amino acid ester derivatives. These novel macrocycles have been shown to be strong complexing agents for primary organic ammonium salts (with K values of up to 1363.5 M-1, Delta G degrees of up to 17.86 kJ mol(-1) and a selectivity ratio of 80:20) by H-1 NMR titration method. These macrocyclic host exhibited enantioselective binding towards the L-enantiomer of phenylalanine methyl ester hydrochloride with K-L/K-D up to 8.57 in CDCl3 containing 0.25% CD3OD. Experimental results have been detailed with molecular dynamic calculations at atomic level concerning the molecular recognition and discrimination properties of a chiral pyridino-15-crown-5. The binding free energies were calculated as similar to-25 kJ mol(-1). The results indicated that the host binds and discriminates valine salts better than phenylalanine salts. The molecular dynamics, MM/PBSA calculations are consistent with the H-1 NMR results. (C) 2010 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [107 T 079]en_US
dc.description.sponsorshipWe would like to thank to The Scientific and Technological Research Council of Turkey (TUBITAK) for their financial support (Project No: 107 T 079) and Professor Necmettin Pirinccioglu for allowing us to use his computer facilities.en_US
dc.identifier.doi10.1016/j.tetasy.2010.05.038
dc.identifier.endpage996en_US
dc.identifier.issn0957-4166
dc.identifier.issue8en_US
dc.identifier.scopus2-s2.0-77954315627
dc.identifier.scopusqualityN/A
dc.identifier.startpage990en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2010.05.038
dc.identifier.urihttps://hdl.handle.net/11468/16106
dc.identifier.volume21en_US
dc.identifier.wosWOS:000280120700017
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keyword]en_US
dc.titlePyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulationsen_US
dc.titlePyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulations
dc.typeArticleen_US

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