Fluorescence Chiral Derivatization Reagents for High Performance Liquid Chromatographic Resolution of Enantiomeric Hydroxyl Compounds¹

Abstract

Two sensitive and moderately reactive chiral derivatization reagents having a binaphthalene moiety as a fluorophore and carbonyl cyanide as a reacting group toward enantiomeric alcohols have been developed. The derivatization reagents, (—)- and (+)-2-methyl-1,1′-binaphthalene-2′-carbonyl cyanides, were prepared from dimethyl-1,1′-binaphthalene-2,2′-dicarboxylate in several steps. Enantiomeric alcohols underwent facile derivatization with these reagents under mild condition. The diastereomeric esters formed from enantiomeric β-hydroxy acids and β-blockers were efficiently resolved by high performance liquid chromatography on a normal phase column. The resulting esters were highly responsive to a fluorescence detector (excitation wavelength 342 nm; emission wavelength 420 nm), the limit of detection being 200 pg.