Development of new isothiocyanate-based chiral derivatizing agent for amino acids

(1S,2S)-1,3-Diacetoxy-1-(4-nitrophenyl)-2-propylisothiocyanate [(S,S)-DANI] has been developed as a new chiral derivatizing agent for resolution of co mpounds containing an amino group. The reagent is readily available in both enantiomeric forms. Its applicability was demonstrated by the resolution o f representative alpha-amino acids. The diastereomeric thiourea derivatives produced were separated by reversed-phase (C-18) high-performance liquid c hromatography, with mixtures of 0.1% aqueous trifluoroacetic acid (pK simil ar to 2) and methanol as eluents.