Synthetic studies on glycosphingolipids from Protostomia phyla: synthesis of amphoteric glycolipid analogues containing a phosphocholine residue from the earthworm Pheretima hilgendorfi.
Two kinds of amphoteric glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows: The key reaction is a coupling of a phosphocholine group at the position C-6 of 1 and 6 which 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 2 and 7. Subsequent debenzylation afforded target compounds (3, 8). Their ability to inhibit the histamine release in vitro was examined.
Hada
N
N
Kyoritsu College of Pharmacy,Tokyo, Japan.
Sato
K
K
Sakushima
J I
JI
Goda
Y
Y
Sugita
M
M
Takeda
T
T
D000818:Animals; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006633:Histamine Antagonists / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006636:Histamine Release / Q000187:drug effects / Q000502:physiology; D009835:Oligochaeta / Q000737:chemistry*; D010767:Phosphorylcholine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D014407:Tumor Cells, Cultured
D006017:Glycolipids; D006028:Glycosphingolipids; D006633:Histamine Antagonists; D010767:Phosphorylcholine