Synthesis and chain length–anti-HIV activity relationship of fully N- and O-sulfated homooligomers of tyrosine Original Research Article

Fully N- and O-sulfated homooligomers from octamer to nonadecamer of tyrosine were obtained as their sodium salts, NaO3S–[Tyr(SO3Na)]n–ONa (n=8–19), from reaction mixtures of tyrosine with sulfur trioxide trimethylamine and pyridine complexes, respectively, in pyridine. Their anti-HIV activity increased along with the increase of the chain length up to the dodecamer, maintained the same level to the length of the heptadecamer and then decreased. The maximal activity level was the same as or higher than that of dextran and curdlan sulfates.