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Characterization of sulfated β ‐cyclodextrins and determination of enantiomeric purity of (1 R, 2 S )‐ephedrine by capillary zone electrophoresis
Author(s) -
Amini Ahmad,
Rundlöf Torgny,
Grön Rydberg MayBritt,
Arvidsson Torbjörn
Publication year - 2004
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.200401843
Subject(s) - chemistry , capillary electrophoresis , enantiomer , ephedrine , chromatography , sulfation , mass spectrometry , cyclodextrin , electrophoresis , analytical chemistry (journal) , stereochemistry , biochemistry , neuroscience , biology
Matrix‐assisted laser‐desorption ionization time‐of‐flight (MALDI–TOF) mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy were employed to characterize two different sulfated β‐cyclodextrins (HS‐β‐CD). It was found that the HS‐β‐CDs have broad heterogeneity in terms of sulfation degree. The average sulfate contents were in the range of 6 to 8 per CD molecule. Furthermore the sugar moieties of both HS‐β‐CDs were sulfated either at position 6 or at positions 2 and 6, but not at position 3. Enantiomeric separation by capillary zone electrophoresis (CZE) using the HS‐β‐CDs as chiral selectors showed that these CDs exhibited similar chiral selectivity and resolution of the ephedrine enantiomers. One of the CDs was employed for the enantiomeric purity evaluation of (1 R ,2 S )‐ephedrine (or (–)‐ephedrine) by capillary zone electrophoresis. Quantification was done by comparison between the corrected peak areas of the minor enantiomer and (–)‐ephedrine.