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Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry
Author(s) -
Chankvetadze Bezhan,
Burjanadze Naira,
Pintore Giorgio,
Strickmann Dirk,
Bergenthal Dieter,
Blaschke Gottfried
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:8<635::aid-chir5>3.0.co;2-d
Subject(s) - chemistry , electrospray ionization , capillary electrophoresis , mass spectrometry , chromatography , electrospray , capillary electrophoresis–mass spectrometry , nuclear magnetic resonance spectroscopy , analytical chemistry (journal) , organic chemistry
Capillary electrophoresis (CE) allows the observation of the opposite affinities of the enantiomers of (±)‐verapamil [2‐isopropyl‐2,8‐bis(3,4‐dimethoxyphenyl)‐6‐methyl‐6‐azaoctannitrile, VP] toward β‐cyclodextrin (β‐CD) and heptakis(2,3,6‐tri‐O‐methyl)‐β‐CD (TM‐β‐CD). In addition, in the presence of β‐CD in the background electrolyte, longer migration times and lower separation factors were observed compared to TM‐β‐CD. The binding constants of (+)‐ and (−)‐VP with β‐CD and TM‐β‐CD determined using 13 C NMR spectroscopy explain the results observed in CE. Electrospray ionization mass spectrometry (ESI‐MS) was used as an alternative technique for the characterization of VP‐CD complexes. Chirality 11:635–644, 1999. © 1999 Wiley‐Liss, Inc.