K. Kohata et al., SYNTHESIS AND CHARACTERIZATION OF NEW STYLE OF WATER-SOLUBLE GLYCOSYLATED PORPHYRINS AS A SPECTROPHOTOMETRIC REAGENT FOR METAL-IONS, Bulletin of the Chemical Society of Japan, 67(3), 1994, pp. 668-679
Six new styles of water-soluble glycosylated porphyrins (5, 10, 15, 20
-tetrakis[2-, 3- or 4-(beta-D-glucopyranosyl) phenyl]porphine) were sy
nthesized and studied concerning their structures by H-1 and C-13 NMR.
Tetrakis (o-substituted phenyl)porphine, consisting of four atropisom
ers (alphabetaalphabeta, alphaalphabetabeta, alphaalphaalphabeta, and
alphaalphaalphaalpha), was clearly assigned based on the C-13 NMR peak
-splitting pattern. It was especially noteworthy that water-soluble pi
cket-fence porphyrin (alphaalphaalphaalpha) was obtained. Furthermore,
their characterization as a chromogenic reagent for metal ions was in
vestigated. The introduction of highly water-soluble glucose successfu
lly improved the aggregration and adsorption characteristics of the an
ionic or cationic porphyrins so far prepared without any marked change
in the other important analytical properties.