Enantioselective inclusion between terbutaline enantiomers and hydroxypropyl-β-cyclodextrin

Solid inclusion complexes between terbutaline (racemate, S-(+)-enantiomer, and R-(-)-enantiomer, respectively) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) were prepared by the lyophilization method. Characterization of each complex was achieved with differential scanning calorimetry (DSC). Stoichiometry between terbutaline and HP-beta-CD was studied by UV spectroscopy, and stability constants between terbutaline (racemic, S-(+)-enantiomer and R-(-)-enantiomer) and HP-beta-CD was also determined by UV absorption and chromatographic retention method. Structural study to confirm exact location of chiral discrimination between terbutaline enantiomers and HP-beta-CD was performed by H-1 NMR spectroscopy. From this experiment, enantioselective binding of terbutaline enantiomers to HP-beta-CD was clearly demonstrated. (C) 1998 Published by Elsevier Science B.V. All rights reserved.