Journal
JOURNAL OF SEPARATION SCIENCE
Volume 33, Issue 11, Pages 1617-1624Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jssc.201000040
Keywords
Capillary electrophoresis; Cyclodextrins; Enantiomer migration order; NMR spectroscopy; Propranolol; Separation mechanisms
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Funding
- Georgia National Science Foundation (GNSF) [GNSF/ST 06/071]
- Merck Research Laboratories (USA)
- Belgium National Fund for Scientific Research (FNRS)
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In the present study the migration order of the propranolol enantiomers with various native CDs and neutral and charged CD derivatives was examined in capillary electrophoresis (CE). The reversal of the enantiomer migration order was observed due to sulfation of beta-CD on its primary hydroxy groups. The structures of intermolecular selector-select and temporary diastereomeric associates in solution were elucidated based on 1D rotating frame nuclear Overhauser effect spectroscopy (1D ROESY) experiments. Major structural differences were observed between the propranolol complexes with native beta-CD and heptakis(6-O-sulfo)-beta-CD.
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