Synthesis and Characterization of New Style of Water-Soluble Glycosylated Porphyrins as a Spectrophotometric Reagent for Metal Ions

Article abstract of DOI:10.1246/bcsj.67.668

Six new styles of water-soluble glycosylated porphyrins (5,10,15,20-tetrakis<2-, 3- or 4-(β-D-glucopyranosyl)phenyl>porphine) were synthesized and studied concerning their structures by 1H and 13C NMR.Tetrakis (o-substituted phenyl)porphine, consisting of four atropoisomers (αβαβ, ααββ, αααβ, and αααα), was clearly assigned based on the 13C NMR peak-splitting pattern.It was especially noteworthy that water-soluble picket-fence porphyrin (αααα) 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.