Electrokinetic chromatography employing an anionic and a cationic β‐cyclodextrin derivative
- 1 January 1997
- journal article
- Published by Wiley in Electrophoresis
- Vol. 18 (6), 897-904
- https://doi.org/10.1002/elps.1150180608
Abstract
β‐Cyclodextrin, 1, can act as a chiral buffer additive in capillary zone electrophoresis (CZE) owing to its ability to form diastereomeric complexes with the enantiomers of ionic compounds. Reaction of 1 with 2,3‐epoxy‐propyltrimethylammonium chloride gave preponderantly 6‐O‐(2‐hydroxy‐3‐trimethyl‐ammoniopropyl) derivatives (2) of varying degrees of substitution (d.s.). Analogous reaction of 1 with 1,3‐propanesultone yielded 6‐O‐(sulfo‐n‐propyl) derivatives (SPE‐β‐CD, 3) of varying d.s. The purity and the d.s. of 2 and 3 were determined by 1H NMR and electrospray ionization mass spectrometry (ESI‐MS). These charged β‐cyclodextrin derivatives were used for the chromatographic enantiomer separation of a series of neutral barbiturates, of chlorthalidone, terbutaline, warfarin, salbutamol and brompheniramine by cyclodextrin electrokinetic chromatography (CD‐EKC). During the separation of chlorthalidone with 3 as chiral additive, a reversible interconversion of the enantiomers (enantiomerization) was observed at temperatures below 20°C.Keywords
This publication has 42 references indexed in Scilit:
- Influence of Substituents on the Rotational Energy Barrier of Axially Chiral Biphenyls, IIEuropean Journal of Organic Chemistry, 1996
- Organic Stereochemistry and Conformational Analysis from Enantioselective Chromatography and Dynamic Nuclear Magnetic Resonance MeasurementsAccounts of Chemical Research, 1995
- Racemization, enantiomerization, diastereomerization, and epimerization: Their meaning and pharmacological significanceChirality, 1995
- About some aspects of the use of charged cyclodextrins for capillary electrophoresis enantioseparationElectrophoresis, 1994
- Derivatized cyclodextrins for the separation of enantiomers in capillary electrophoresisJournal of High Resolution Chromatography, 1993
- Separation of the enantiomers of some racemic nonsteroidal aromatase inhibitors and barbiturates by capillary electrophoresisChirality, 1993
- Characterization of sulphoalkyl ether derivatives of β-cyclodextrin by capillary electrophoresis with indirect UV detectionJournal of Pharmaceutical and Biomedical Analysis, 1992
- Electrokinetic chromatography: An interface between electrophoresis and chromatographyTrAC Trends in Analytical Chemistry, 1989
- Hydrolysis of nitrophenyl esters catalyzed by modified cyclodextrin in water pools in reversed micelles.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984
- Properties of Cyclodextrins. Part VI. Water‐Soluble Cyclodextrin‐Derivatives. Preparation and AnalysisStarch ‐ Stärke, 1971