Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives

Demirtas H. N., BOZKURT S., Durmaz M., Yilmaz M., Sirit A.

Tetrahedron, cilt.65, sa.15, ss.3014-3018, 2009 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 65 Sayı: 15
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1016/j.tet.2009.01.087
  • Dergi Adı: Tetrahedron
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3014-3018
  • Uşak Üniversitesi Adresli: Evet

Özet

In this study the synthesis of novel chiral calix[4]azacrown derivatives has been reported. The enantioselectivity of chiral receptors was investigated by using UV-vis spectroscopy. All the chiral calix[4]arene derivatives exhibited certain chiral recognition toward the enantiomers of phenylalanine (Phe-OMe·HCl) and alanine methyl ester hydrochlorides (Ala-OMe·HCl). As a chiral receptor, the furfuryl-armed calix[4]azacrown ether 7 has the best enantiomeric discriminating ability for α-amino acid ester hydrochlorides (up to KL/KD=2.08, ΔΔG0=-1.82 kJ mol-1) in CHCl3. The enantiomeric recognition abilities for guests are also discussed from a thermodynamic point of view. © 2009 Elsevier Ltd. All rights reserved.