Exhaustively substituted bile acids as chiral selectors for enantioselective chromatography: Aim, use and perspectives

The use of chiral stationary phases (CSPs) obtained from cholic and deoxycholic acid derivatives in the HPLC resolution of racemic compounds is presented. The CSPs containing arylcarbamoyl derivatives of bile acids show enantiodiscriminating capabilities depending on the electronic character of the aryl substituents: the CSPs obtained starting from heteroderivatized selectors, i.e. bile acid derivatives containing both π-acidic and π-basic arylcarbamoyl moieties, show enantiodiscriminating capabilities strongly dependent on the arrangement of the electronically different arylcarbamates on the cholestanic backbone. The CSPs obtained starting from deoxycholic acid derivatives possessing both arylamido and arycarbamoyl substituents show enantiodiscriminating capabilities restricted to the resolution of benzodiazepine derivatives. Again, the enantioresolution properties depend not only on the electronic nature of the aromatic substituents but also on their arrangement on the cholestanic backbone. The comparison among the different families of bile acid based CSPs allows us to find likeness and differences in the enantiorecognition mechanism exhibited by the different chiral selectors.