New chiral derivatization reagent for the resolution of amino acids as diastereomers by TLC and HPLC

Summary

The applicability of a new chiral reagent to the resolution of amino acid enantiomers has been investigated. The new reagent, S(-)-N-1-(2-naphthylsulphonyl)-2-pyrrolidinecarbonyl chloride (NSP-C1), was synthesized by the chlorination of S(-)-N-1-(2-naphthylsulphonyl)-2-pyrrolidinecarboxylic acid which was prepared by the reaction of 2-naphthalene sulphonyl chloride with L-proline. Derivatization of the amino acids proceeds rapidly at ambient temperature and no racemization takes place during the reaction. The resolution of the diastereomeric amides was performed by TLC and normal phase HPLC. Complete resolutions were observed for the enantiomers of all amino acids examined except cysteine, cystine and histidine. The favourable UV absorption of the derivatives enabled the optical antipode to be determined down to the 0.1% level.