Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of a glycosphingolipid analogue from the parasite Spirometra erinacei.
Novel neutral glycosphingolipids isolated from the plerocercoids of a tapeworm, Spirometra erinacei, may be expected to be involved in host-parasite interactions. We have synthesized this glycosphingolipid analogue containing 2-branched fatty alkyl residue in place of ceramide. Glycosylation of nonreducing-end trisaccharide derivative 15 with the reducing-end disaccharide derivative 17 in the presence of trimethylsilyl triflate (TMSOTf) gave the desired oligosaccharide derivative in good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycoside 19 was converted to glycosylimidate 20, which was condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated to give the target glycosphingolipid analogue 22.
Hada
N
N
Kyoritsu College of Pharmacy, Tokyo, Japan.
Kuroda
M
M
Takeda
T
T
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013146:Spirometra / Q000737:chemistry*
D006028:Glycosphingolipids