P. Maillard et al., GLYCOCONJUGATED PORPHYRINS .2. SYNTHESIS OF STERICALLY CONSTRAINED POLYGLYCOSYLATED COMPOUNDS DERIVED FROM TETRAPHENYLPORPHYRINS, Journal of organic chemistry, 58(10), 1993, pp. 2774-2780
A variety of glycoconjugated porphyrins has been synthesized by Lindse
y's method from pyrrole and o-acetylglycosylated benzaldehyde precurso
rs. Deprotection of glucose and maltose moieties allows the production
of derivatives which had a good solubility in neutral aqueous solutio
n and covered a range of amphiphilic character. The structure in solut
ion 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 hindran
ce of both faces of the porphyrin macrocycle. The present strategy sho
uld prove applicable to the synthesis of other glycoconjugated tetrapy
rrolic compounds.