This research project, supported by the Analytical and Surface Chemistry Program, seeks to develop methods for the characterization of chiral compounds using lanthanide ion based chemical shift reagents in nuclear magnetic resonance spectroscopy (NMR). Cyclodextrins are used as chiral complexing agents, and lanthanide chelates are chemically coupled to the cyclodextrins. Chemical shifts are observed in the NMR spectra which are dependent on which enantiomer is complexed by the cyclodextrin. This study addresses an important problem in biotechnology and pharmaceutical research. Many physiologically active drugs are only effective in one configuration; the chemically identical mirror image of the compound may be totally ineffective. It is therefore critical to be able to determine the composition of mixtures of these mirror image compounds (enantiomers) that result from the synthetic procedure. The methodology based on magnetic resonance spectroscopy being developed at Bates College will allow two enantiomers to be distinguished, and may also allow the absolute configuration of the compounds to be determined.
