Sensitive Fluorescence Labeling Reagents for High Performance Liquid Chromatography of Carbonyl Compounds1

Abstract

Highly sensitive and moderately reactive derivatization reagents having an anthracene moiety as a fluorophore and carboxylic acid hydrazide of O-aralkylhydroxylamine as a reacting group toward the carbonyl function have been developed. The derivatization reagents, anthracene-1- and 2-carboxylic acid hydrazides and O--(1-, 2- and 9-anthrylmethyl)-hydroxylamines, were readily prepared from the corresponding anthracenecarboxylic acids in several steps. The carbonyl compounds underwent facile derivatization with these reagents under mild conditions. The resulting hydrazones and oximes were highly responsive to a fluorescence detector in high performance liquid chromatography, the limits of detection being 50 and 20fmol, respectively.