Development of Highly Sensitive Analytical Systems to Determine the Absolute Configuration of Chiral Compounds

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With aims to develop highly sensitive ways to determine the absolute configurations of chiral molecules, new type of chiral derivatizing agents, (+)-TBMB and (+)-TBB carboxylic acids were designed and prepared. The absolute configurations of the former was determined to be (2S) by X-ray analysis of the L-phenylalanie derivative. They were designed to have a CD (circular dichroism) chromophore, isolated Me groups and fluorescent in the bodies which can be effectively used in the CD, NMR and HPLC analyzes to determine the absolute configuration and the optical purity of chiral molecules.Targets for applying these two reagents were directed to three biomolecules, carbohydrates, amino acids and glycerolipids. The analytical conditions were investigated for the derivatization, purification, separations and detections for each. Consequently, simple and highly sensitive methods were established to analyze the D, L-isomers. For sugars and amino acids, NMR and HPLC were effectively employed in the system. For glycerolipids, circular dichroism (CD) based on exciton chirality way was coupled with HPLC system to build a simultaneous system to determine the absolute configuration and the optical purity. This system was employed in the study on the stereochemistries of lipase-catalyzed hydrolysis of glycerides.