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 sulfaton 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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Katsuraya, K., Jeon, KJ., Nakashima, H. et al. NMR Studies on Structure and Action Mechanism of Sulfated Dodecyl Laminaripentaoside with High Anti-Human Immunodeficiency Virus Activity. Polym J 31, 924–928 (1999). https://doi.org/10.1295/polymj.31.924
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DOI: https://doi.org/10.1295/polymj.31.924