Integrated experimental and theoretical approaches to investigate the molecular mechanisms of the enantioseparation of chiral anticonvulsant and antifungal compounds


Gambacorta N., ÖZDEMİR Z., DOĞAN İ. S., Ciriaco F., ZENNİ Y. N., KARAKURT A., ...Daha Fazla

Journal of Molecular Structure, cilt.1270, 2022 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1270
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.molstruc.2022.133905
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Amylose tris(3,5-dimethyphenylcarbamate), Arylalkylazole, Chiralpak AD, Enantioseparation, Molecular modeling and dynamics
  • Hacettepe Üniversitesi Adresli: Evet

Özet

© 2022 Elsevier B.V.Previously, some racemic 1-(phenyl/4-chlorophenyl)-2-(1H-triazole-1-yl)ethanol ester derivatives having a stereogenic center in their structure were synthesized and investigated for their anticonvulsant and antifungal activities. In this work, the direct enantiomeric separations of four compounds (1–4) were developed on the commercially available chiral stationary phase amylose tris(3,5-dimethyphenylcarbamate) (Chiralpak AD) in the normal phase HPLC mode. The influences of the mobile phase composition were also investigated. By mobile phase modified with n-hexane, the retention times were shorter than with methanol. The best results were obtained for all compounds (1–4) using the mobile phase of methanol/n-hexane (80:20 v/v) at a flow rate of 0.5 mL/min and the resolutions of the enantiomers were 3.38, 2.84, 1.89, and 1.53, respectively. Thus, the proposed HPLC method can facilitate further chemical and pharmacological studies on compounds 1–4 and their enantiomers. In addition, the molecular mechanism behind the possible chiral recognition was discussed based on the experimental and theoretical results of the enantiomeric separation and molecular dynamics studies.