Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection.
Katsuraya K, Ikushima N, Takahashi N, Shoji T, Nakashima H, Yamamoto N, Yoshida T, Uryu T
Institute of Industrial Science, University of Tokyo, Japan.
A series of sulfated alkyl oligosaccharides, including a sulfate 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 oligosaccharide 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 exclusively, the acetylation was carried out with a sodium acetate-acetic anhydride at high temperatures to maximize the proportion of the beta anomer.
PMID: 8062289, UI: 94340624