1 Ocak 2010 Dergi makalesi Açık Erişim

Turgut, Yilmaz; Kocakaya, Safak Ozhan

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  <dc:creator>Turgut, Yilmaz</dc:creator>
  <dc:creator>Kocakaya, Safak Ozhan</dc:creator>
  <dc:date>2010-01-01</dc:date>
  <dc:description>Two 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.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/23497</dc:identifier>
  <dc:identifier>oai:zenodo.org:23497</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>TETRAHEDRON-ASYMMETRY 21(8) 990-996</dc:source>
  <dc:title>Pyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulations</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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