1 Ocak 2010 Dergi makalesi Açık Erişim

Turgut, Yilmaz; Kocakaya, Safak Ozhan

Citation Style Language JSON

{
  "DOI": "10.1016/j.tetasy.2010.05.038", 
  "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.", 
  "author": [
    {
      "family": "Turgut", 
      "given": " Yilmaz"
    }, 
    {
      "family": "Kocakaya", 
      "given": " Safak Ozhan"
    }
  ], 
  "container_title": "TETRAHEDRON-ASYMMETRY", 
  "id": "23497", 
  "issue": "8", 
  "issued": {
    "date-parts": [
      [
        2010, 
        1, 
        1
      ]
    ]
  }, 
  "page": "990-996", 
  "title": "Pyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulations", 
  "type": "article-journal", 
  "volume": "21"
}