The synthesis of sugar-decorated hydrophilic porphyrins

Abstract

The synthesis of porphyrins conjugated with sugar moieties is described. meso-Aminophenyl-substituted and β-amino-substituted porphyrin derivatives reacted with benzyl protected glucuronic acid leading to gluco-conjugated hybrids, which after reductive deprotection of OH groups ( H2, 10% Pd/C ) gave the desired target products of increased hydrophilicity. Alternatively, this type of similar conjugates were obtained through SNAr reaction of meso-tetrakis(pentafluorophenyl)porphyrin with aminomethyl sacharides. The substitution took place selectively in para-position of meso-perfluorophenyl rings, thus giving rise to one, two, or three times substituted products carrying N-linked glucoside residues.