SYNTHESIS AND CHARACTERIZATION OF NEW STYLE OF WATER-SOLUBLE GLYCOSYLATED PORPHYRINS AS A SPECTROPHOTOMETRIC REAGENT FOR METAL-IONS

Six new styles of water-soluble glycosylated porphyrins (5, 10, 15, 20-tetrakis[2-, 3- or 4-(beta-D-glucopyranosyl) phenyl]porphine) were synthesized and studied concerning their structures by H-1 and C-13 NMR. Tetrakis (o-substituted phenyl)porphine, consisting of four atropisomers (alphabetaalphabeta, alphaalphabetabeta, alphaalphaalphabeta, and alphaalphaalphaalpha), was clearly assigned based on the C-13 NMR peak-splitting pattern. It was especially noteworthy that water-soluble picket-fence porphyrin (alphaalphaalphaalpha) was obtained. Furthermore, their characterization as a chromogenic reagent for metal ions was investigated. The introduction of highly water-soluble glucose successfully improved the aggregration and adsorption characteristics of the anionic or cationic porphyrins so far prepared without any marked change in the other important analytical properties.