title: Studies of a pyridino-crown ether-based chiral stationary phase on the enantioseparation of biogenic chiral aralkylamines and α-amino acid esters by high-performance liquid chromatography.
abstract: This paper reports the enantioseparation ability of a pyridino-18-crown-6 ether-based chiral stationary phase [(S,S)-CSP-1]. The enantiomeric discrimination of chiral stationary phase (S,S)-CSP-1 was evaluated by HPLC using the mixtures of enantiomers of various protonated primary aralkylamines [1-phenylethylamine hydrogen perchlorate (PEA), 2,3-dihydro-1H-inden-1-amine (1-aminoindan), 2,2'-(1,2-diaminoethane-1,2-diyl) diphenol (HPEN)] and perchlorate salts of α-amino acid esters [alanine benzyl ester (Ala-OBn), phenylalanine benzyl ester (Phe-OBn), phenylalanine methyl ester (Phe-OMe), phenylglycine methyl ester (PhGly-OMe), glutamic acid dibenzyl ester (Glu-diOBn), and valine benzyl ester (Val-OBn)]. The best enantioseparation was achieved in the case of PEA. The high enantioselectivity was rationalized by the strong π-π interaction of the extended π system of the aryl-substituted pyridine unit.
authors.affiliation: Compound Profiling Laboratory, Chemical Works of Gedeon Richter Plc., H-1475 Budapest, PO Box 27, Hungary.
authors.forename: Sándor
authors.initials: S
authors.lastname: Lévai
authors.affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary.
authors.forename: Tamás
authors.initials: T
authors.lastname: Németh
authors.affiliation: Compound Profiling Laboratory, Chemical Works of Gedeon Richter Plc., H-1475 Budapest, PO Box 27, Hungary.
authors.forename: Tamás
authors.initials: T
authors.lastname: Fődi
authors.affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary.
authors.forename: József
authors.initials: J
authors.lastname: Kupai
authors.affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary.
authors.forename: Tünde
authors.initials: T
authors.lastname: Tóth
authors.affiliation: Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, PO Box 91, Hungary.
authors.forename: Péter
authors.initials: P
authors.lastname: Huszthy
authors.affiliation: Compound Profiling Laboratory, Chemical Works of Gedeon Richter Plc., H-1475 Budapest, PO Box 27, Hungary. Electronic address: gy.balogh@richter.hu.
authors.forename: György Tibor
authors.initials: GT
authors.lastname: Balogh
mesh_terms: D000596:Amino Acids / Q000302:isolation & purification*; D001679:Biogenic Amines / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001679:Biogenic Amines; D043844:Crown Ethers; D004952:Esters; D011725:Pyridines
keywords: Chiral stationary phase; Crown ether; Enantiomeric separation; HPLC; Pyridine