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Separation of terbutaline enantiomers in capillary electrophoresis with neutral cyclodextrin‐type chiral selectors and investigation of the structure of selector‐selectand complexes using nuclear magnetic resonance spectroscopy
Author(s) -
Gogolashvili Ann,
Chankvetadze Lali,
Takaishvili Nino,
Salgado Antonio,
Chankvetadze Bezhan
Publication year - 2020
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.202000010
Subject(s) - enantiomer , chemistry , cyclodextrin , nuclear magnetic resonance spectroscopy , capillary electrophoresis , spectroscopy , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , terbutaline , crystallography , chromatography , medicine , asthma , physics , quantum mechanics
Abstract The major goal of this study was to determine the affinity pattern of the terbutaline (TB) enantiomers toward α‐, β‐, γ‐, and heptakis(2,3‐di‐ O ‐acetyl)‐β‐cyclodextrins and using NMR spectroscopy for the understanding of the fine mechanisms of interaction between the cyclodextrins (CD) and TB enantiomers. It was shown once again that CE in combination with NMR spectroscopy represents a sensitive tool to study the affinity patterns and structure of CD complexes with chiral guests. Opposite affinity patterns of TB enantiomers toward native α‐ and β‐CDs were associated with significant differences between the structure of the related complexes in solution. In particular, the complex between TB enantiomers and α‐CD was of the external type, whereas an inclusion complex was formed between TB enantiomers and β‐CD. One of the possible structures of the complex between TB and heptakis(2,3‐di‐ O ‐acetyl)‐β‐CD (HDA‐β‐CD) was quite similar to that of TB and β‐CD, although the chiral recognition pattern and enantioselectivity of TB complexation with these two CDs were very different.