High-performance liquid chromatographic methods for separation of the isomers of β-amino acids possessing bicyclo[2.2.1]heptane or heptene skeletons

• Published in: Journal of Chromatography A 1998-02, Vol.797 (1-2), p.177-186
• Main Authors: Török, Gabriella, Péter, Antal, Csomós, Peter, Kanerva, Liisa T, Fülöp, Ferenc
• Format: Article
• Language: English
• Subjects: Amino acids; Analytical chemistry; Bicycloheptane amino acids; Chemistry; Chromatographic methods and physical methods associated with chromatography; Exact sciences and technology; Other chromatographic methods
• ISSN: 0021-9673
• DOI: 10.1016/S0021-9673(97)00948-5

Reversed-phase high-performance liquid chromatographic methods were developed for separation and identification of the enantiomers of bicyclic β-amino acids: racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo-(1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-bicyclo[2.2.1]heptane-2-carboxylic acids and racemic diendo-(1S,2S,3R,4R and 1R,2R,3S,4S) and diexo-(1S,2R,3S,4R and 1R,2S,3R,4S)-3-amino-5-bicyclo[2.2.1]heptene-2-carboxylic acids. The enantioselective separations were carried out in two ways: separation of the diastereomers formed by precolumn derivatization with the 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-glucopyranosyl isothiocyanate, and direct separation by the application of a chiral stationary phase, Crownpak CR(+). The results of the methods were compared and optimal conditions were developed in systematic chromatographic examinations.