Syntheses and Application of the Functional Compounds Designed to Study the Metabolism and the Mechanism of the Action of Vitamin D

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1)To develop an accurate and precise method for assaying vitamin D metabolites in plasma, reagents to label vitamin D with fluorescence or chemoluminescence were designed and synthesized.2)A highly fluorescent dienophile(named DMEQ-TAD), in which a fluorescent chromophore(dimethoxyquinoxalinone group)and a highly reactive dienophile(1, 2, 4-triazoline-3, 5-dione)were connected via a spacer, was successfully synthesized for the first time.3)The reaction of the fluorescent dienophile(DMEQ-TAD)with major vitamin D_3 metabolites was examined and it was shown that all the metabolites were fluorescence-labeled in quantitative yields.4)Fluorometry of plasma vitamin D metabolites was examined and new accurate fluorometric methods for assaying 25(OH)D_3 and 24, 25(OH)_2D_3 in plasma were developed.5)A new and convenient stereoselective method for synthesizing 1, 25(OH)_2D_3 26, 23-lactone, a major metabolite of the active vitamin D_3, was developed.6)Reaction of vitamin A derivatives with DMEQ-TAD was examined and it was shown that they react with the reagent with high regioselectivity indicating that the reagent might be useful for assaying the active vitamin A metabolite.