Separation of brombuterol enantiomers in capillary electrophoresis with cyclodextrin-type chiral selectors and investigation of structure of selector-selectand complexes using nuclear magnetic resonance spectroscopy

Gogolashvili A., Tatunashvili E., Chankvetadze L., Sohajda T., GÜMÜŞTAŞ M., Ozkan S. A., ...Daha Fazla

Electrophoresis, cilt.40, sa.15, ss.1904-1912, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 40 Sayı: 15
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1002/elps.201900062
  • Dergi Adı: Electrophoresis
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1904-1912
  • Anahtar Kelimeler: Brombuterol, Cyclodextrins, Enantiomer migration order, Selector-selectand complexes, Separation of enantiomers, NATIVE BETA-CYCLODEXTRIN, STATIONARY PHASES, MIGRATION ORDER, RESOLVING AGENT, ENANTIOSEPARATIONS, NMR, PROPRANOLOL, RECOGNITION, DERIVATIVES, MECHANISMS
  • Ankara Üniversitesi Adresli: Evet

Özet

© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, WeinheimThe major goal of this study was to determine the affinity pattern of brombuterol (BB) enantiomers toward various cyclodextrins (CD) and to evaluate the potential of NMR spectroscopy for understanding fine mechanisms of interactions between CDs and BB enantiomers. Separation of BB enantiomers was performed in a fused-silica capillary using a phosphate buffer, pH 2.5, at the room temperature in the normal polarity mode. It was shown once again that CE in combination with NMR spectroscopy represents a very sensitive tool for studies of affinity patterns and structure of CD complexes with chiral guests. Although opposite affinity patterns of BB enantiomers were observed toward native β- and γ-CDs, no significant differences between the structures of the complexes of these two CDs with BB were detected by NMR spectroscopy. In contrary to this, the opposite affinity pattern of BB enantiomers toward β-CD and its two sulfated derivatives, heptakis (2,3-O-diacetyl-6-sulfo)-β-CD (HDAS-β-CD) and heptakis (2-O-methyl-3,6-di-O-sulfo)-β-CD (HMDS-β-CD) was associated with major differences in the structure of the complexes. In addition, it was shown again that HMDS-β-CD provides separation of enantiomers without formation of inclusion-type complex with the chiral analyte.