Synthesis and biological activities of lipid A-type pyrancarboxylic acid derivatives.
The synthesis of lipid A-type pyrancarboxylic acid derivatives, which have a carboxylic acid group in the anomeric position of the reducing part of the disaccharide instead of the phosphate group in lipid A, is described. One of the compounds thus synthesized, which has an acyl substitution pattern similar to that of Escherichia coli lipid A, showed lipopolysaccharide (LPS)-agonistic activity. The other, which contains four lipid chains in the molecule, exhibited strong LPS-antagonistic activity toward human monoblastic U937 cells.
Mochizuki
T
T
Exploratory Chemistry Research Laboratories, Sankyo Co. Ltd., Tokyo, Japan.
Iwano
Y
Y
Shiozaki
M
M
Kurakata
S
S
Kanai
S
S
Nishijima
M
M
D002236:Carbohydrate Conformation; D002264:Carboxylic Acids / Q000138:chemical synthesis; D004187:Disaccharides / Q000138:chemical synthesis; D004926:Escherichia coli; D006801:Humans; D008050:Lipid A / Q000031:analogs & derivatives* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000138:chemical synthesis; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism; D020298:U937 Cells
D002264:Carboxylic Acids; D004187:Disaccharides; D008050:Lipid A; D008070:Lipopolysaccharides; D011714:Pyrans; D014409:Tumor Necrosis Factor-alpha