Histamine-modified cationic β-cyclodextrins as chiral selectors for the enantiomeric separation of hydroxy acids and carboxylic acids by capillary electrophoresis

Galaverna, Gianni; Corradini, Roberto; Dossena, Arnaldo; Marchelli, Rosangela

doi:10.1002/(sici)1522-2683(19990901)20:13<2619::aid-elps2619>3.0.co;2-x

Cited by 40 publications

(14 citation statements)

References 48 publications

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“…As previously reported [17][18][19][20] and recently reviewed [21], CCE studies can be usefully supported by NMR data. The cyclopeptide cY and its complexes with the Dnp-Glu and C7 enantiomers were analyzed by NMR spectroscopy in order to throw light upon the chiral recognition mechanism.…”

Section: Nmr Datasupporting

confidence: 57%

Chiral capillary electrophoresis and nuclear magnetic resonance investigation on the structure-enantioselectivity relationship in synthetic cyclopeptides as chiral selectors

et al. 2001

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In the present work, synthetic cyclohexa- and cycloheptapeptides previously singled out by a combinatorial chemistry approach have been evaluated as chiral selectors in capillary electrophoresis. By applying the countercurrent migration technique and employing a new adsorbed coating, a series of dinitrophenyl amino acids as well as some chiral compounds of pharmaceutical interest have been evaluated for enantiorecognition. The results thus obtained led to a deeper investigation of the chiral discrimination process, by carrying out nuclear magnetic resonance (NMR) studies on selected cyclopeptide-analyte complexes. These studies shed light on the chemical groups involved in the analyte-selector interaction and provided useful information for a wider application of these cyclopeptides in the separation of other drug enantiomers.

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Section: Nmr Datasupporting

confidence: 57%

Chiral capillary electrophoresis and nuclear magnetic resonance investigation on the structure-enantioselectivity relationship in synthetic cyclopeptides as chiral selectors

et al. 2001

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“…Galaverna et al recently introduced histamine-modified cationic b-cyclodextrins as chiral selectors and demonstrated their applicability to chiral separation by means of Dns-amino acids, carboxylic acids and hydroxy acids [361].…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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“…It was shown that the conditional association constants, between the CM-û-CD and tripeptides, decrease with increasing pH may be due to a decrease in ionic interactions. A basic and mono substituted b-CD (6-deoxy-6-N-histamine-b-CD) at a concentration of 1 mM (pH 4 or 5) enabled enantiomeric separation of hydroxy and carboxylic acids [109]. The authors investigated the mechanism of enantioseparation by MS and NMR and found that both hydrophobic and electrostatic interactions were involved in chiral separations.…”

Section: Charged Cdsmentioning

confidence: 99%

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

Ahmad

2001

Electrophoresis

186

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This paper provides an overview of the current status of chiral capillary electrophoresis (CE). The emphasis is placed on the application of CE in chiral separation of various racemic compounds. During the last two years about 280 papers, several review articles, and two entire issues, edited by S. Fanali (Electrophoresis 1999, 20, 2577-2798, and H. Nishi and S. Terabe (J. Chromatogr. A 2000, 879, 1-471.) have been devoted to chiral CE. Enantiomeric separations of various compounds, e.g., pharmaceuticals, drug candidates, drugs and related metabolites in biological fluids, amino acids, di- and tri peptides, pesticides and fungicides, have been performed using different chiral selectors. Native and derivatized cyclodextrins continue to be the most widely used chiral selectors. Other chiral selectors such as natural and synthetic chiral micelles, crown ethers, chiral ligands, proteins, oligo- and polysaccharides, and macrocyclic antibiotics have also been applied to chiral CE separations.

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Histamine-modified cationic β-cyclodextrins as chiral selectors for the enantiomeric separation of hydroxy acids and carboxylic acids by capillary electrophoresis

Cited by 40 publications

References 48 publications

Chiral capillary electrophoresis and nuclear magnetic resonance investigation on the structure-enantioselectivity relationship in synthetic cyclopeptides as chiral selectors

Chiral capillary electrophoresis and nuclear magnetic resonance investigation on the structure-enantioselectivity relationship in synthetic cyclopeptides as chiral selectors

Chiral separation by chromatographic and electromigration techniques. A Review

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

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