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Capillary electrophoretic and nuclear magnetic resonance studies on the opposite affinity pattern of propranolol enantiomers towards various cyclodextrins
Author(s) -
Servais AnneCatherine,
Rousseau Anne,
Fillet Marianne,
Lomsadze Ketevan,
Salgado Antonio,
Crommen Jacques,
Chankvetadze Bezhan
Publication year - 2010
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/jssc.201000040
Subject(s) - enantiomer , capillary electrophoresis , chemistry , chromatography , capillary action , nuclear magnetic resonance , electrophoresis , propranolol , materials science , stereochemistry , medicine , physics , composite material
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 β‐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 β‐CD and heptakis(6‐ O ‐sulfo)‐β‐CD.