Novel chiral stationary phases derived from natural compounds

In the joint project between the University of Chemistry and Technology Prague and the University of Natural Resources and Life Sciences, Vienna (BOKU), novel innovative high-tech chiral stationary phases based on natural compounds for the separation of enantiomers should be developed. The analytical and preparative separation of such enantiomers is an omnipresent challenge in medical, pharmaceutical, and chemical disciplines. The chiral stationary phase materials should be based both on natural small molecules such as Cinchona alkaloids as well as natural polymeric/oligomeric compounds like cellulose and cellooligomers. The materials as well as selected structural units of them will be chemically modified by carbamoylation before being either physically coated or chemically immobilized onto silica as an HPLC support material. Characterization of the novel materials will inter alia be carried out by liquid- and solid-state NMR, FTIR, elemental analysis, HP(T)LC, TGA, and MALDI-MS. After packing into stainless steel columns, the enantioseparation behavior of the novel materials will be evaluated with a set of chiral/racemic compounds and non-racemic mixtures. A set of semi-synthetic analytes based on natural amino acids will also be synthesized by both project partners. Evaluation of the enantioseparation performance will be mostly done by HPLC, but also solid-state NMR studies, if applicable, for further investigating molecular interactions between the chiral analytes in solution and the respective chiral selectors on silica in a solid/swollen state.