GLYCOCONJUGATED PORPHYRINS .2. SYNTHESIS OF STERICALLY CONSTRAINED POLYGLYCOSYLATED COMPOUNDS DERIVED FROM TETRAPHENYLPORPHYRINS

A variety of glycoconjugated porphyrins has been synthesized by Lindsey's method from pyrrole and o-acetylglycosylated benzaldehyde precursors. Deprotection of glucose and maltose moieties allows the production of derivatives which had a good solubility in neutral aqueous solution and covered a range of amphiphilic character. The structure in solution of these new compounds was studied by H-1 NMR analysis. A study of the complexation characteristics of their zinc derivatives shows low values of affinity constants which are dependent on the steric hindrance of both faces of the porphyrin macrocycle. The present strategy should prove applicable to the synthesis of other glycoconjugated tetrapyrrolic compounds.