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M9490658.TXT
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1994-09-24
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Document 0658
DOCN M9490658
TI Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with
potent inhibitory effects on AIDS virus infection.
DT 9411
AU Katsuraya K; Ikushima N; Takahashi N; Shoji T; Nakashima H; Yamamoto N;
Yoshida T; Uryu T; Institute of Industrial Science, University of Tokyo,
Japan.
SO Carbohydr Res. 1994 Jul 4;260(1):51-61. Unique Identifier : AIDSLINE
MED/94340624
AB 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.
DE Acetylation Antiviral Agents/CHEMICAL SYNTHESIS/*PHARMACOLOGY
Carbohydrate Sequence Fatty Alcohols/CHEMISTRY Glycosylation
HIV-1/*DRUG EFFECTS Molecular Sequence Data Oligosaccharides/CHEMICAL
SYNTHESIS/*PHARMACOLOGY Polysaccharides/*PHARMACOLOGY Sulfuric Acid
Esters JOURNAL ARTICLE
SOURCE: National Library of Medicine. NOTICE: This material may be
protected by Copyright Law (Title 17, U.S.Code).