1 Ocak 2010 Dergi makalesi Açık Erişim

Turgut, Yilmaz; Kocakaya, Safak Ozhan

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/23497</identifier>
  <creators>
    <creator>
      <creatorName>Turgut, Yilmaz</creatorName>
      <givenName>Yilmaz</givenName>
      <familyName>Turgut</familyName>
      <affiliation>Dicle Univ, Fac Sci, Dept Chem, TR-21280 Diyarbakir, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Kocakaya, Safak Ozhan</creatorName>
      <givenName>Safak Ozhan</givenName>
      <familyName>Kocakaya</familyName>
      <affiliation>Dicle Univ, Fac Sci, Dept Chem, TR-21280 Diyarbakir, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Pyridine-Containing Chiral Macrocycles For The Enantioselective Recognition Of Amino Acid Derivatives And Their Molecular Dynamics Simulations</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2010</publicationYear>
  <dates>
    <date dateType="Issued">2010-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/23497</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1016/j.tetasy.2010.05.038</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">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.</description>
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