Abstract
Anti-HIV (human immunodeficiency virus) active sulfated dodecyl laminaripentaosides having various degrees of sulfation were synthesized and their structures 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 sulfated, followed by the sulfation of the 2-hydroxyl and the 4-hydroxyl, in the sulfation of dodecyl laminaripentaoside. Interactions between sulfated dodecyl laminaripentaoside and poly- or oligo-lysine as a virus protein model compound were analyzed. The reason why high degree of sulfation was necessary for obtaining high anti-HIV activity in vitro was strong ionic interactions 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.
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