Sensitive Derivatization Reagents for Optical Resolution of Carboxylic Acids by High Performance Liquid Chromatography with Fluorescence Detection

Abstract

Two highly sensitive, chiral derivatization reagents, 1-(1-anthryl)- and 1-(2-anthryl)ethylamines, have been developed. Condensation of carboxylic acids with the chiral reagent was effected in the presence of water-soluble carbodiimide and 1-hydroxybenzotriazole. The diastereomeric amides formed from N-acetylamino acid and naproxen enantiomers were efficiently resolved by normal phase chromatography (Resolve 5μ Spherical Silica column) with hexane/ethyl acetate as a mobile phase. With a fluorescence detector (excitation 260 nm, emission 400 nm), the detection limit was 100 fmol (S/N=10).