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Novel, switchable chiral stationary phases


Function and properties of molecules depend on their three dimensional (stereo) structure. The structure is determined not only by types of atoms and bonds but also by its symmetry and chirality. The last phenomenon concerns the molecules (stereoisomers) w hich remain in the relation object-its mirror image and thus are not superimposable. Stereoisomers exhibit usualy dramatical differences in their biological activity. One stereoisomer can be active drug, the second (mirror image) can possess no activity or be even harmfull (story of Thalidomide). Selection of the appropriate stereoisomer offers therefore benefits of better therapeutical profile of drug and the reduction of the dose and side effects.There is tremendous demand for developing new tools for sep aration stereoisomers either for preparative (production) or for analytical purposes (research, medical studies, quality control). Desiging of new chiral stationary phases for chromatograpic separation meets this demand. The goal of this project is the syn thesis and evaluation of novel, chiral stationary phases. These exhibit many unique features: - are switchable - can adopt their shape to the shapes of analysed molecules (selectands), - contain Cinchona alkaloid molecules which are known for numerous appl ication in organic synthesis as catalysts, resolving agents and single chiral phases. They are also widely available, relatively cheap and non-toxic, - are of C2 symmetry (which is very rare in the common chiral selectors, but very succesfull in the field of stereoselective synthesis and molecular recognition), - have many binding sites crucial for molecular recognition. My preliminary studies showed that compunds of this group efficiently recognize either achiral or chiral molecules. Based on these results and results obtained by host, it can be anticipated that these selectors when supported can serve as novel, efficient stationary phases for either chiral or achiral recognition.

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Dr.-Karl-Lueger-Ring 1

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