Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum.
A novel amphoteric glycosphingolipid, cholinephosphoryl-(-->6)-beta-D-GlcpNAc-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->)-Cer, isolated from the porcine parasitic nematode, Ascaris suum, may be expected to be involved in host-parasite interactions. This glycosphingolipid analogue containing octyl residue in place of ceramide was synthesized as follows: The key reaction of this synthetic procedure is the formation of a intramolecular aglycon delivery (IAD) approach for beta-selective mannosylation. Then, a coupling of phosphocholine group at the position C-6'' of 16 was attempted using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by reaction of the resulting cyclic phosphate intermediate with anhydrous trimethylamine to give 17. Subsequent debenzylation and debenzylidenation afforded target compound (2).
Ohtsuka
Isao
I
Kyoritsu College of Pharmacy, Tokyo, Japan.
Hada
Noriyasu
N
Ohtaka
Hiroko
H
Sugita
Mutsumi
M
Takeda
Tadahiro
T
D000818:Animals; D017165:Ascaris suum / Q000737:chemistry*; D006017:Glycolipids / Q000138:chemical synthesis / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000737:chemistry; D013552:Swine
D006017:Glycolipids; D006028:Glycosphingolipids; D007202:Indicators and Reagents; D009844:Oligosaccharides