Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection.
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.
Katsuraya
K
K
Institute of Industrial Science, University of Tokyo, Japan.
Ikushima
N
N
Takahashi
N
N
Shoji
T
T
Nakashima
H
H
Yamamoto
N
N
Yoshida
T
T
Uryu
T
T
D000107:Acetylation; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D005233:Fatty Alcohols / Q000737:chemistry; D005936:Glucans; D006031:Glycosylation; D015497:HIV-1 / Q000187:drug effects*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000494:pharmacology*; D011134:Polysaccharides / Q000494:pharmacology*; D013463:Sulfuric Acid Esters
D000998:Antiviral Agents; D005233:Fatty Alcohols; D005936:Glucans; D009844:Oligosaccharides; D011134:Polysaccharides; D013463:Sulfuric Acid Esters; C021705:maltooligosaccharides; C008247:laminaran