Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids.
Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcbeta-(1 --> 3)-Man and GalNAcbeta-(1 --> 4)-GlcNAcbeta-(1 --> 3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer and beta-D-GalNAcp-(1 --> 4)-beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages.
Ohtsuka
Isao
I
Kyoritsu College of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
Hada
Noriyasu
N
Sugita
Mutsumi
M
Takeda
Tadahiro
T
D000818:Animals; D017165:Ascaris suum / Q000737:chemistry*; D005643:Fucose; D006028:Glycosphingolipids / Q000138:chemical synthesis*; D007448:Invertebrates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose; D009005:Monosaccharides / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis
D006028:Glycosphingolipids; D009005:Monosaccharides; D009844:Oligosaccharides; D005643:Fucose; D008358:Mannose