SYNTHESIS AND USE OF A NOVEL CHIRAL SURFACTANT BASED ON (R,R)-TARTARIC ACID AND ITS APPLICATION TO CHIRAL SEPARATIONS IN MICELLAR ELECTROKINETIC CAPILLARY CHROMATOGRAPHY (MECC)

This article describes the synthesis of a novel chiral surfactant base d on (R,R)-tartaric acid. (R,R)-Tartaric acid is acetylated while simu ltaneously forming a cyclic anhydride, which is then reacted with n-de cylamine forming a chiral, long chain carboxylic acid. This carboxylic acid is then further reacted with the achiral amino acid taurine form ing the required surfactant which has a sulfonic acid headgroup. Evide nce for its surface activity and an estimate of its critical micelle c oncentration (cmc) have been obtained using surface tension measuremen ts and conductivity. The surfactant has then been used as the additive in micellar electrokinetic capillary chromatography (MECC) to achieve chiral separations of compounds with multiple aromatic functionality. These separations are compared with those achieved with previously re ported tartaric acid based surfactants which show a difference in sele ctivity. (C) 1995 John Wiley & Sons, Inc.