title: Cyclodextrin-mediated enantioseparation of phenylalanine amide derivatives and amino alcohols by capillary electrophoresis-role of complexation constants and complex mobilities.
abstract: The separation of the enantiomers of phenylalanine amide and N-methyl derivatives as well as some amino alcohols was studied by CE in acidic BGEs using CDs as chiral selectors. The native CDs displayed only low chiral recognition ability at a concentration of 15 mg/mL in 20 mM sodium phosphate buffer, pH 2.5. In contrast, the analyte enantiomers were separated in the presence of randomly sulfated CDs under reversed polarity of the applied voltage. Sulfated β-CD proved to be the most universal selector resulting in the enantioseparation of all analytes. Opposite enantiomer migration order depending on the size of the CD cavity was observed for phenylalanine amide and 2-amino-2-phenylethanol. The R-enantiomers migrated first in the presence of sulfated α-CD and γ-CD while the S-enantiomers were detected first in the presence of sulfated β-CD. The enantioseparations could be rationalized based on analyte complexation by the respective CDs except for 2-amino-2-phenylethanol and sulfated β-CD where essentially equal complexation constants were derived for the enantiomers. In this case, the migration behavior could be attributed to the mobilities of the enantiomer-CD complexes adding another example to the CE-specific phenomenon of enantioseparations based primarily on complex mobilities.
authors.affiliation: Department of Inorganic and Analytical Chemistry, University of Szeged, Szeged, Hungary; Department of Pharmaceutical Chemistry, Friedrich Schiller University of Jena, Jena, Germany.
authors.forename: Anita
authors.initials: A
authors.lastname: Aranyi
authors.forename: Antal
authors.initials: A
authors.lastname: Péter
authors.forename: István
authors.initials: I
authors.lastname: Ilisz
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
authors.forename: Gerhard K E
authors.initials: GK
authors.lastname: Scriba
mesh_terms: D000605:Amino Alcohols / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D003505:Cyclodextrins / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000295:instrumentation* / Q000379:methods; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D003505:Cyclodextrins; D010649:Phenylalanine; C020457:phenylalanine amide
keywords: Amino alcohol; Binding constants; Enantiomer separation; Highly sulfated cyclodextrin; Phenylalanine amide