Chromatographic Resolution of Enantiomers on Chiral Ion Exchanger: Conceptional Reflections

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Abstract:

Over the recent years the chromatographic resolution of enantiomers of very different chemical structure has become state of the art. In this lecture first the underlying stereoselective molecular recognition principles will be discussed followed by a focus on the enantiomer separation of chiral acids, bases and ampholytes using chiral ion exchange type stationary phases (CSPs) which we developed in our laboratory. As chiral template for selector development we selected the quinine and quinidine motif and systematically modified these pseudo-enantiomerically behaving moieties to reach optimised and dedicated chiral selectors to be then immobilised onto porous silica thus leading to the CSPs and chiral columns.

These novel materials proved to be particularly successful for the challenging resolutions of e.g. free amino acids, short peptides, etc. On the basis of such type applications we will further discuss the parameters influencing the retention and stereoselectivity characteristic of these CSPs being used in liquid (LC) and super critical fluid chromatographic (SFC) mode.

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