Novel methods in chromatographic separations: new chiral stationary phases and molecular tagging

Abstract

CHEMISTRY

NOVEL METHODS IN CHROMATOGRAPHIC SEPARATIONS: NEW CHIRAL STATIONARY PHASES AND MOLECULAR TAGGING

JORDAN DANIELLE HANEY BLODGETT

Dissertation under the direction of Professor David M. Hercules A major obstacle for many chemists is the retrieval of desired compounds from a mixture resulting from a chemical reaction or from a complex analytical sample. Even more challenging is the need to separate enantiomers of the same compound from each other. In the past the determination of chiral selectors for chiral HPLC has largely been an empirical process requiring large amounts of time in order to develop new selectors for difficult separations. It is therefore of great importance to pursue methods for faster screening of selectors for a given analyte. We report a powerful method for the screening of peptide-based chiral selectors in a high-throughput manner using parallel combinatorial library technology. In addition, since the practical synthesis of organic compounds is limited not only by yield of specific reactions but also by the ability to isolate products efficiently, strategies to facilitate product isolation are an important development. A new tagging system based on the interaction of beta-cyclodextrin and the 4-tert-butylphenyl group will be described to address this need.