FLUORESCENCE CHIRAL DERIVATIZATION REAGENTS FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC RESOLUTION OF ENANTIOMERIC HYDROXYL COMPOUNDS

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. © 1990, The Japan Society for Analytical Chemistry. All rights reserved.