Lipid A and related compounds. XXIX. Synthesis of biologically active N-acylated L-asparagine-containing D-glucosamine derivatives structurally related to lipid A.
New beta-N-acylated L-asparagine-linked D-glucosamine derivatives, in which the reducing unit of lipid A has been mimicked by a lipoamino acid, have been synthesized. Compounds 1 and 2 exhibit mitogenicity and nitric oxide (NO) productivity.
Suhara
Y
Y
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Arakawa
M
M
Ikeda
K
K
Achiwa
K
K
D000818:Animals; D002455:Cell Division / Q000187:drug effects; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D008050:Lipid A / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D017737:Macrophages, Peritoneal / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008934:Mitogens / Q000138:chemical synthesis* / Q000494:pharmacology; D009569:Nitric Oxide / Q000096:biosynthesis*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared
D008050:Lipid A; D008934:Mitogens; D009569:Nitric Oxide; D005944:Glucosamine