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Mechanistic study on the opposite migration order of the enantiomers of ketamine with α‐ and β‐cyclodextrin in capillary electrophoresis
Author(s) -
Chankvetadze Bezhan,
Burjanadze Naira,
Breitkreutz Jörg,
Bergander Klaus,
Bergenthal Dieter,
Kataeva Olga,
Fröhlich Roland,
Luftmann Heinrich,
Blaschke Gottfried
Publication year - 2002
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/1615-9314(20021101)25:15/17<1155::aid-jssc1155>3.0.co;2-m
Subject(s) - capillary electrophoresis , enantiomer , chemistry , cyclodextrin , mass spectrometry , chromatography , electrospray ionization , capillary electrochromatography , nuclear overhauser effect , electrospray , nuclear magnetic resonance spectroscopy , analytical chemistry (journal) , stereochemistry
The enantiomer migration order of the chiral anaesthetic drug ketamine [ RS ‐2‐(2‐chlorophenyl)‐2‐(methylamino)cyclohexanone] was studied by capillary electrophoresis using various cyclodextrins as chiral selectors. The opposite migration order of the enantiomers of ketamine was observed when native α‐ and β‐cyclodextrins were used as chiral selectors in capillary electrophoresis. The possible mechanisms of the opposite enantiomer migration order were investigated by employing electrospray ionization mass spectrometry, 1 H‐NMR spectrometry, one dimensional rotating frame nuclear Overhauser and exchange spectroscopy, X‐ray crystallography, and molecular modeling techniques. As this study indicates, capillary electrophoresis can be used as a reliable experimental technique for examination of the correctness of the results of molecular modeling calculations. In addition, based on X‐ray crystallographic analysis it was confirmed that (–)‐ketamine as a free base possesses S configuration.