Synthesis of N-acetylglucosaminyl- and N-acetylgalactosaminylceramides as cerebroside analogs and their anti-human immunodeficiency virus type 1 activities.
Monoglycosylceramide derivatives containing mimicks of ceramide were synthesized as cerebroside analogs from D-glucosamine or D-galactosamine derivatives and N-benzyloxycarbonyl-L-serine myristylamide by using trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a promoter. The synthesized sulfate glycolipids show moderate anti-HIV-1 activities.
Ikeda
K
K
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Asahara
T
T
Achiwa
K
K
Hoshino
H
H
D000116:Acetylgalactosamine / Q000737:chemistry; D002554:Cerebrosides / Q000737:chemistry* / Q000494:pharmacology; D005944:Glucosamine / Q000737:chemistry; D006017:Glycolipids / Q000737:chemistry; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy
D002554:Cerebrosides; D006017:Glycolipids; D000116:Acetylgalactosamine; D005944:Glucosamine