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Synthesis of sulfated alkyul malto and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection

A series of sulfated alkyl oligosaccharides, including a sulfated dodecyl laminarapentaoside and a sulfated octadecyl maltohexaoside with potent anti-human immunodeficiency virus (HIV) activity, has been synthesized. An alkyl oligosaccharide in which a long alkyl group is bonded to the reducing end...

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Bibliographic Details
Published in:Carbohydrate research 1994-01, Vol.260 (1), p.51-61
Main Authors: Katsuraya, Kaname, Ikushima, Naoya, Takahashi, Nahoko, Shoji, Tadao, Nakashima, Hideki, Yamamoto, Naoki, Yoshida, Takashi, Uryu, Tsohiyuki
Format: Article
Language:English
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Summary:A series of sulfated alkyl oligosaccharides, including a sulfated dodecyl laminarapentaoside and a sulfated octadecyl maltohexaoside with potent anti-human immunodeficiency virus (HIV) activity, has been synthesized. An alkyl oligosaccharide in which a long alkyl group is bonded to the reducing end of the oligosaccahride was first synthesized in high yield. Peracetylated oligosaccharides reacted with such aliphatic alcohols as 1-decyl and 1-dodecyl alcohols with Lewis acids as catalysts. As in the glycosylation of the alpha and beta peracetylated glycosides, the beta anomer reacted exlusively, the acetylation was carried out with a sodium acetate-acetic anhydride at high temperatures to maximize the proportion of the B anomer.
ISSN:0008-6215