SYNTHESIS AND STRUCTURAL-ANALYSIS OF CURDLAN SULFATE WITH A POTENT INHIBITORY EFFECT INVITRO OF AIDS VIRUS-INFECTION

The inhibitory effects against a human immunodeficiency virus (HIV) in vitro and the structural studies on curdlan sulfate were investigated. Curdlan, a natural linear (1→3)-β-D-glucan, was sulfated by piperidine-N-sulfonic acid in dimethyl sulfoxide to give curdlan sulfates with several molecular sizes and different sulfur contents. Curdlan sulfate with a sulfur content of 14.4% completely inhibited the infection of HIV in the drug concentration of as low as 3.3 μg/mL. This is one of the most potent anti-AIDS viral polysaccharides. The high-resolution NMR analysis including COSY and RELAYED-COSY experiments revealed that for a polymer with the number of sulfate groups per glucose unit (DS) of 1.6 the sulfate group was introduced to C6, C4, and C2 positions of the glucose unit, respectively. © 1990, American Chemical Society. All rights reserved.