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

Reversed-phase high-performance liquid chromatographic methods were developed for separation and identification of the enantiomers of bicyclic beta-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.l]hep 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-beta-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. (C) 1998 Elsevier Science B.V.