NMR studies on structure and action mechanism of sulfated dodecyl laminaripentaoside with high anti-human immunodeficiency virus activity

Anti-HIV (human immunodeficiency virus) active sulfated dodecyl laminaripen taosides having various degrees of sulfation were synthesized and their str uctures analyzed by 2D NMR spectroscopic measurements such as C-H direct, C -H long-range, H-H direct, NOESY, and HOHAHA. The 6-hydroxyl was first sulf ated, followed by the sulfation of the 2-hydroxyl and the 4-hydroxyl, in th e sulfation of dodecyl laminaripentaoside. Interactions between sulfated do decyl laminaripentaoside and poly- or oligo-lysine as a virus protein model compound were analyzed. The reason why high degree of sulfaton was necessa ry for obtaining high anti-HIV activity in vitro was strong ionic interacti ons existed between oligo-lysine and sulfated laminaripentaosides with high degree of sulfation. In the gel formed by the interaction the local motion of the sulfated oligosaccharide was restricted to a large extent, whereas that of the alkyl portion was not restricted so much.