The utility of the fluorescence derivatixation reagents, 4-(N,N-dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-l-yl)_2,1,3-benzoxadiaxole [ R( + J-DBD-Pro-CCC1 and S( -)-DBD-Pro-CCC11 with compounds having various functional groups has been evaluated. Enantiomers of DBD-Pro-COCI were equally reactive with alcohols, arnines, phenol and aniline, whereas carboxylic acids and thiols did not yield fluorescent derivatives. The reaction conditions were optimized with a model alcohol (l-heptanol) and a model amine (n-heptylamine). Derivatixation of alcohols and amines in benzene with 1% pyridine provides optimum yields of the corresponding fluorescence ester and amide derivatives. The excitation (ca. 450 nm) and emission (ca. 560 nm) maxima were essentially the same for all alcohols and amines tested. The corresponding derivatives of nine alcohols and three amines were completely separated by reversed-phase chromatography. The detection limits (signal-to-noise ratio of 2) with conventional fluorescence detection using a xenon arc lamp were from 10 fmol to 500 fmol, while those with laser-induced fluorescence (LIF) detection using argon-ion at 488 nm were in the range of 2 fmol to 10 fmol.