Chemical Modification of the N-Acetyl Moieties of Hyaluronic Acid from Streptococcus equi for Studies in Cytokine Production.

Partial N-deacetylation and certain N-reacylations of low-molecular-weight hyaluronic acid (hyaluronan) abate its proinflammatory properties in mammalian systems. Here, we describe the treatment of bacterial hyaluronic acid by hydrazine or NaOH to yield smaller partially deacetylated polymers. These N-deacetylated polymers can be reacylated with acyl anhydrides to yield substituted hyaluronic acid derivatives of equivalent size and equimolar N-acyl substitutions.