title: Enantioseparation of ß-carboline derivatives on polysaccharide- and strong cation exchanger-based chiral stationary phases. A comparative study.
abstract: In this study we attempted to describe in a comparative manner the enantioselectivity performance of six different polysaccharide- and two strong cation exchanger-type chiral stationary phases (CSPs) for the resolution of free and N-protected β-carboline derivatives. On commercially available cellulose- or amylose-based CSPs, the enantioseparations were carried out in normal-phase mode by variation of the nature and the concentration of the alcohol modifier in n-hexane as mobile phase. With the application of strong cation exchanger-type CSPs, the enantioseparations were optimized by the variation of methanol-acetonitrile bulk solvent compositions in the presence of various amounts of acid and base additives acting as counter-ions. Detailed thermodynamic investigations revealed that in all cases the enantioseparations observed were enthalpically driven, i.e. the retention and selectivity decreased with increasing temperature. Elution sequences were determined routinely; no general rule was found on polysaccharide-based CSPs, while on the two enantiomeric strong cation exchanger-type CSPs the predicted reversal of the elution sequence could be confirmed on switching from one enantiomeric CSP to the other form.
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 7, Hungary; Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
authors.forename: Gyula
authors.initials: G
authors.lastname: Lajkó
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 7, Hungary; Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
authors.forename: Nóra
authors.initials: N
authors.lastname: Grecsó
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
authors.forename: Rita
authors.initials: R
authors.lastname: Megyesi
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
authors.forename: Enikő
authors.initials: E
authors.lastname: Forró
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
authors.affiliation: Department of Analytical Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna, Austria.
authors.forename: Denise
authors.initials: D
authors.lastname: Wolrab
authors.affiliation: Department of Analytical Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna, Austria.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Lindner
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 7, Hungary.
authors.forename: Antal
authors.initials: A
authors.lastname: Péter
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 7, Hungary. Electronic address: ilisz@chem.u-szeged.hu.
authors.forename: István
authors.initials: I
authors.lastname: Ilisz
mesh_terms: D000688:Amylose / Q000737:chemistry; D002243:Carbolines / Q000737:chemistry*; D002411:Cation Exchange Resins / Q000737:chemistry; D002482:Cellulose / Q000737:chemistry; D002623:Chemistry Techniques, Analytical / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D000431:Ethanol / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; D002411:Cation Exchange Resins; D006586:Hexanes; D011134:Polysaccharides; D012997:Solvents; C026385:n-hexane; D000431:Ethanol; D002482:Cellulose; D000688:Amylose
keywords: Enantiomer separation; Polysaccharide-based chiral stationary phases; Strong cation exchanger-type chiral stationary phases; Temperature effect; ß-carboline derivatives