2001Biomedical ChromatographyRequires access

Separation of chiral 4‐substituted imidazole derivatives by cyclodextrin‐modified capillary electrophoresis

Astrid Sasse, Walter Schunack, Holger Stark

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Abstract

Enantiomeric separations by cyclodextrin-modified capillary electrophoresis of chiral carbamates containing a 4-substituted imidazole heterocycle, pharmacologically acting as histamine H3-receptor antagonists, were carried out. Various cyclodextrins (α-, β- and substituted β-cyclodextrins) were investigated. Baseline resolution was achieved with six out of 11 compounds. Heptakis-2,3,6-trimethyl-β-cyclodextrin modified buffers seemed to be most efficient in separating most of the investigated compounds. The optical purity of one pair of enantiomers was determined. Copyright © 2001 John Wiley & Sons, Ltd. Abbreviations used: α-CD α-cyclodextrin β-CD β-cyclodextrin CD cyclodextrins CE capillary electrophoresis CM-β-CD carboxymethylated-β-cyclodextrin DM-β-CD heptakis-2,6-dimethyl-β-cyclodextrin DS average degree of substitution ee enantiomeric excess HE-β-CD 2-hydroxyethyl-β-cyclodextrin HP-β-CD 2-hydroxypropyl-β-cyclodextrin i.d. inner diameter LOD limit of detection LOQ limit of quantification Rs resolution SBE-cd sulphobutylether-β-cyclodextrin SO4-β-CD sulphated-β-cyclodextrin TM7hyphen;β-CD heptakis-2,3,6-trimethyl-β-cyclodextrin

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Enantiomeric separations by cyclodextrin-modified capillary electrophoresis of chiral carbamates containing a 4-substituted imidazole heterocycle, pharmacologically acting as histamine H3-receptor antagonists, were carried out. Various cyclodextrins (α-, β- and substituted β-cyclodextrins) were investigated. Baseline resolution was achieved with six out of 11 compounds. Heptakis-2,3,6-trimethyl-β-cyclodextrin modified buffers seemed to be most efficient in separating most of the investigated compounds. The optical purity of one pair of enantiomers was determined. Copyright © 2001 John Wiley & Sons, Ltd. Abbreviations used: α-CD α-cyclodextrin β-CD β-cyclodextrin CD cyclodextrins CE capillary electrophoresis CM-β-CD carboxymethylated-β-cyclodextrin DM-β-CD heptakis-2,6-dimethyl-β-cyclodextrin DS average degree of substitution ee enantiomeric excess HE-β-CD 2-hydroxyethyl-β-cyclodextrin HP-β-CD 2-hydroxypropyl-β-cyclodextrin i.d. inner diameter LOD limit of detection LOQ limit of quantification Rs resolution SBE-cd sulphobutylether-β-cyclodextrin SO4-β-CD sulphated-β-cyclodextrin TM7hyphen;β-CD heptakis-2,3,6-trimethyl-β-cyclodextrin

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Available abstract

Enantiomeric separations by cyclodextrin-modified capillary electrophoresis of chiral carbamates containing a 4-substituted imidazole heterocycle, pharmacologically acting as histamine H3-receptor antagonists, were carried out. Various cyclodextrins (α-, β- and substituted β-cyclodextrins) were investigated. Baseline resolution was achieved with six out of 11 compounds. Heptakis-2,3,6-trimethyl-β-cyclodextrin modified buffers seemed to be most efficient in separating most of the investigated compounds. The optical purity of one pair of enantiomers was determined. Copyright © 2001 John Wiley & Sons, Ltd. Abbreviations used: α-CD α-cyclodextrin β-CD β-cyclodextrin CD cyclodextrins CE capillary electrophoresis CM-β-CD carboxymethylated-β-cyclodextrin DM-β-CD heptakis-2,6-dimethyl-β-cyclodextrin DS average degree of substitution ee enantiomeric excess HE-β-CD 2-hydroxyethyl-β-cyclodextrin HP-β-CD 2-hydroxypropyl-β-cyclodextrin i.d. inner diameter LOD limit of detection LOQ limit of quantification Rs resolution SBE-cd sulphobutylether-β-cyclodextrin SO4-β-CD sulphated-β-cyclodextrin TM7hyphen;β-CD heptakis-2,3,6-trimethyl-β-cyclodextrin

Key concepts: Cyclodextrin, Chemistry, Capillary electrophoresis, Enantiomer, Imidazole, Chromatography, Detection limit, Chiral resolution

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