High-performance liquid chromatographic methods for separation of enantiomers of alicyclic β-amino acids

• Published in: Journal of Chromatography A Vol. 761; no. 1; pp. 103 - 113
• Main Authors: PETER, A, TÖRÖK, G, CSOMOS, P, PETER, M, BERNATH, G, FÜLÖP, F
• Format: Journal Article Conference Proceeding
• Language: English
• Published: Amsterdam Elsevier B.V 14.02.1997; Elsevier
• Subjects: Amino acids; Analytical chemistry; Chemistry; Chromatographic methods and physical methods associated with chromatography; Derivatization, LC; Enantiomer separation; Exact sciences and technology; Other chromatographic methods; Amino acids; Enantiomer separation; Derivatization, LC; Capacity factor; Peak resolution; Flow rate; Separation; Phase composition; Precolumn; HPLC chromatography; Temperature effect; Crown compound; Chiral stationary phase; Derivatization; Mobile phase; Chiral selector; Reversed phase chromatography; Chemical modification; Carboxylic acid; Aminoacid; Enantiomer; pH; Monocyclic compound; Ethylenic compound; Diastereomer; Comparative study; Quantitative analysis
• ISSN: 0021-9673
• DOI: 10.1016/S0021-9673(96)00832-1

Reversed-phase high-performance liquid chromatographic methods were developed for the separation and quantification of the enantiomers of alicyclic β-amino acids: racemic cis- and trans-2-aminocyclohexane-1-carboxylic acids ( cis- and trans-ACHC) and racemic cis- and trans-2-animon-4-cyclohexene-1-carboxylic acids ( cis- and trans-ACHC-ene). The enantioselective separations involved two methods: direct separation on a chiral stationary phase (Crownpak CR(+)) and separation of the diastereomers formed by pre-column derivatization with chiral derivatizing reagents: 1-fluoro-2,4-dinitrophenyl-5- l-alanine amide (Marfey's reagent) and 2,3,4,6-tetra-O-acetyl-β- d-glucopyranosylisothiocyanate. The different methods were compared in systematic chromatographic examinations. The effects of pH, mobile phase composition, organic modifier content and temperature on the separation were also investigated.