Preparation and Characterization of <em>O</em>-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

Abstract

Fucosylated chondroitin sulfate (FuCS), a kind of complex glycosaminoglycan from sea cucumber, has potent anticoagulant activity. In order to understand the relationship between structures and activity, the depolymerized FuCS (dFuCS) was chosen to prepare its derivates by selective substitution at OH groups. Its <em>O</em>-acylation was carried out in a homogeneous way using carboxylic acid anhydrides. The structures of<em> O</em>-acylated derivatives were characterized by NMR. The results indicated that the 4-<em>O</em>-sulfated fucose residues may be easier to be acylated than the other ones in the sulfated fucose branches. But the<em> O</em>-acylation was always accompanied by the β-elimination, and the degree of elimination was higher as that of acylation was higher. The results of clotting assay indicated that the effect of partial <em>O</em>-acylation of the dFuCS on their anticoagulant potency was not significant and the <em>O</em>-acylation of 2-OH groups of 4-<em>O</em>-sulfated fucose units did not affect the anticoagulant activity.

Keywords

• sea cucumber
• fucosylated chondroitin sulfate
• glycosaminoglycan
• acylation
• anticoagulant activity