CHIRAL SEPARATION OF AMINES BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHYAFTER TAGGING WITH AMINOSULPHONYL)-7-(2-CHLOROFORMYLPYRROLIDIN-1-YL)-2,1,3-BENZOXADIAZOLE

Chiral tagging reagents, -chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadi azole (R(+)-DBD-Pro-COCl and S(-)-DBD-Pro-COCl), react with mirror ima ge enantiomers of amines to produce corresponding diastereomers in the presence of pyridine as a catalyst. The maximal excitation and emissi on wavelengths of the resulting diastereomers were ca. 450nm and 560nm , respectively. The diastereomers derived from some aliphatic amines w ere resolved by a reversed-phase chromatography with water-acetonitril e or normal-phase chromatography with n-hexane-ethyl acetate as the el uent. The reactivities of both enantiomers of DBD-Pro-COCl to chiral a mines were almost comparable, whereas a slight difference of fluoresce nce intensity was observed with S(-)-DBD-Pro-COCl. When S(-)-DBD-Pro-C OCl was used as the derivatization reagent, amines corresponding to S- configuration were eluted faster than R-configuration. The opposite el ution order was obtained with the use of R(+)-DBD-Pro-COCl, instead of S(-)-DBD-Pro-COCl. The R(S) values obtained from 1-cyclohexylethylami ne (CEA) having aliphatic ring structure was larger than those of amin es (1-(1-naphtyl)ethylamine (NEA) and 1-phenylethylamine (PEA)) having aromatic ring structures.