title: High-performance liquid chromatographic separation of the enantiomers of unusual alpha-amino acid analogues.
abstract: The direct and indirect stereochemical resolution of the enantiomers of ring- and alpha-methyl-substituted phenylalanines and phenylalanine amides was attempted by high-performance liquid chromatographic methods. The direct separation was carried out on two chiral stationary phases, the crown-ether-based Crownpak CR(+), and the teicoplanin-based Chirobiotic T, while the indirect resolution was performed by applying pre-column derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC) and Nalpha-(2,4-dinitro-5-fluorophenyl)-L-alanine amide (Marfey's reagent, FDAA). The Chirobiotic T column was efficient in the separation of ring- and alpha-methyl-substituted phenylalanine analogues, but was ineffective for the amides of these analogues. The Crownpak CR(+) column separated the ring-substituted phenylalanines and amides, whereas the alpha-methylated analogues were coeluted. Of the two indirect methods, GITC derivatization seemed more effective than FDAA derivatization.
authors.affiliation: Department of Inorganic and Analytical Chemistry, Attila József University, Szeged, Hungary. apeter@chem.u-szeged.hu
authors.forename: A
authors.initials: A
authors.lastname: Péter
authors.forename: E
authors.initials: E
authors.lastname: Olajos
authors.forename: R
authors.initials: R
authors.lastname: Casimir
authors.forename: D
authors.initials: D
authors.lastname: Tourwé
authors.forename: Q B
authors.initials: QB
authors.lastname: Broxterman
authors.forename: B
authors.initials: B
authors.lastname: Kaptein
authors.forename: D W
authors.initials: DW
authors.lastname: Armstrong
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids