L-CYSTEINE AND D-CYSTEINE DERIVATIVES OF BETA-CYCLODEXTRIN - DIFFERENT MOLECULAR RECOGNITION PROPERTIES OF THEIR COPPER(II) COMPLEXES FOR AMINO-ACIDS

The two epimers of beta-cycIodextrin 6-functionalized with L- or D-cys teine (6-S-(L)-cysteine-6-deoxy-beta-cyclodextrin and (6-S-(D)-cystein e-6-deoxy-beta-cyclodextrin) were synthesized. Their binary and ternar y copper(II) complexes with amino acids were characterized by electron ic, circular dichroism and ESR spectroscopies. The binary copper(II) c omplexes were used as eluents in Ligand exchange chromatography to tes t their ability to resolve racemate mixtures of unmodified amino acids . High performance Liquid chromatography separation of L/D-TrpO(-) was achieved only when the complex of the D-cysteine derivative was used as the eluent. (C) 1998 Elsevier Science S.A. All rights reserved.