Pyridine containing chiral macrocycles: synthesis and their enantiomeric recognition for amino acid derivatives

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dc.contributor.authorDeniz, Pinar
dc.contributor.authorTurgut, Yilmaz
dc.contributor.authorTogrul, Mahmut
dc.contributor.authorHosgoren, Halil
dc.date.accessioned2024-04-24T16:18:25Z
dc.date.available2024-04-24T16:18:25Z
dc.date.issued2011
dc.departmentDicle Üniversitesien_US
dc.description.abstractFour novel C(2)-symmetric enantiomerically pure, chiral pyridine-18-crown-6 type macrocycles containing lipophilic chains at the stereogenic centers were prepared. The enantioselectivity of the new ligands toward the enantiomers of D-,L-amino acid methyl ester derivatives were also determined by (1)H NMR titration method. These novel macrocycles have been showed to be strong complexing agents for D- and L-amino acid methyl ester hydrochloride salts (with K(ass) up to 13590 M(-1) and Delta G(0) up to 23.3 kJ mol(-1) and selectivity ratio: 80:20) by (1)H NMR titration methods. These macrocyclic hosts exhibited enantioselective binding towards the D-enantiomer of valine methyl ester hydrochloride with K(D)/K(L), up to 5.08 in CDCl(3) with 0.25% CD(3)OD. (C) 2011 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [110 T 004]; Dicle University [DUBAP-09-FF-72]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: 110 T 004) and Partial support from Dicle University (Project No: DUBAP-09-FF-72). The authors also would like to thank to Izmir Institute of Technology (IYTE) Biolojical Mass Spectrometry laboratory for taking the MS spectra. We are grateful to Dr. Murat Kizil (Dicle University) for their invaluable contribution.en_US
dc.identifier.doi10.1016/j.tet.2011.06.064
dc.identifier.endpage6232en_US
dc.identifier.issn0040-4020
dc.identifier.issue34en_US
dc.identifier.scopus2-s2.0-79960589912
dc.identifier.scopusqualityQ3
dc.identifier.startpage6227en_US
dc.identifier.urihttps://doi.org/10.1016/j.tet.2011.06.064
dc.identifier.urihttps://hdl.handle.net/11468/16087
dc.identifier.volume67en_US
dc.identifier.wosWOS:000293493900016
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron
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: synthesis and their enantiomeric recognition for amino acid derivativesen_US
dc.titlePyridine containing chiral macrocycles: synthesis and their enantiomeric recognition for amino acid derivatives
dc.typeArticleen_US

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