Sensitive derivatizatton reagents for the resolution of carboxylic acid enantiomers by high-performance liquid chromatography

Abstract

Two highly sensitive, chiral derivatization reagents, D- and L-1-aminoethyl-4-dimethyl-aminonaphthalene, were synthesized from 1-dimethylaminonaphthalene. Condensation of carboxylic acids with the chiral reagent was readily effected in the presence of a watersoluble carbodiimide. The diastereoisomeric amides formed from N-acetylamino acid and α-arylpropionic acid enantiomers were efficiently resolved by normal phase chromatography (μPorasil column) -with hexane/ethyl acetate or hexane/tetrahydrofuran as a mobile phase. With a fluorescence detector (excitation 320 nm, emission 395 nm), the detection limit was 0.1 ng.