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Capillary electrophoresis, nuclear magnetic resonance and mass spectrometry studies of opposite chiral recognition of chlorpheniramine enantiomers with various cyclodextrins
Author(s) -
Chankvetadze Bezhan,
Burjanadze Naira,
Bergenthal Dieter,
Strickmann Dirk,
Blaschke Gottfried,
Pintore Giorgio,
Cerri Riccardo
Publication year - 1998
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.1150191210
Subject(s) - chemistry , capillary electrophoresis , enantiomer , mass spectrometry , cyclodextrin , electrospray ionization , chromatography , diastereomer , electrospray , analytical chemistry (journal) , stereochemistry
Abstract Markedly different chiral separation abilities were observed for native β‐cyclodextrin (β‐CD), carboxymethyl‐β‐CD (CM‐β‐CD) and heptakis (2,3,6‐tri‐ O ‐methyl)‐β‐CD (TM‐β‐CD) towards the enantiomers of (±)‐chlorpheniramine ((±)‐CHL) in capillary electrophoresis (CE). Native β‐CD afforded almost baseline enantioseparation at a concentration of 18 mg/mL, whereas only 1 mg/mL solution of CM‐β‐CD was required for adequate enantioseparation. TM‐β‐CD allowed the nearly baseline enantioseparation only at a concentration as high as 80 mg/mL. Moreover, the migration order of (±)‐CHL in the presence of TM‐β‐CD was opposite to that with β‐CD and CM‐β‐CD. 1 H and 13 C‐NMR spectroscopy and electrospray ionization mass spectrometry (ESI‐MS) have been used in order to obtain preliminary information about the stoichiometry and the binding constants in the intermolecular diastereomeric complexes of (±)‐CHL with these CDs.