Abstract
Chiral derivatization reagents possessing a dansyl (N-dimethylaminoaphthalene-5-sulphonyl) moiety as fluorophore were developed for the separation and sensitive detection of carboxylic acid enantiomers by high-performance liquid chromatography (HPLC). Synthesis of d- and l-1-(4-dansylaminophenyl)ethylamine (DAPEA) from easily obtained starting materials by simple four-step reactions gave satisfactory yields. The reagents reacted with carboxylic acid enantiomers such as anti-inflammatory drugs in the presence of condensing agents (2,2′-dipyridyl disulphide and triphenylphosphine) at room temperature for 2.5 h to give corresponding diastereomeric amide derivatives quantitatively. The fluorescence characteristics of the amide formed from DAPEA with 2-phenylpropionic acid enantiomer (DAPE-PPA) were hardly affected by the pH and water content of the mobile phase in the range commonly used for reversed-phase HPLC. The diastereomeric pairs formed from five anti-inflammatory drugs and phenylpropionic acid with DAPEA were efficiently separated by reversed-phase HPLC. The detection limit (signal-to-noise ratio = 3) of DAPE-PPA, when the resulting derivatization reaction mixture was directly injected on to the column, was 170 fmol per injection.
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