Endotoxic properties of synthetic pentaacyl lipid A precursor Ib and a structural isomer.
A pentaacyl precursor of lipid A biosynthesis, termed precursor Ib, and a structural isomer have been chemically synthesized. These compounds were, in comparison to synthetic Escherichia-coli type lipid A or lipopolysaccharide, analyzed for their activity in typical endotoxin test systems. It was found that both precursor Ib and the isomer exhibited similar or only slightly lower pyrogenic, lethal and Shwartzman-phenomenon-inducing activity than lipid A. All preparations were comparable in their B-lymphocyte mitogenicity, macrophage-activating capacity and immunoreactivity towards lipid A antisera. The proton nuclear magnetic resonance spectra of the 1-dephospho derivative of synthetic and bacterial precursor Ib were indistinguishable proving that the previously proposed structure for precursor Ib is correct.
Rietschel
E T
ET
Institut für Experimentelle Biologie und Medizin, Forschungsinstitut Borstel, Federal Republic of Germany.
Brade
L
L
Schade
U
U
Galanos
C
C
Freudenberg
M
M
Lüderitz
O
O
Kusumoto
S
S
Shiba
T
T
D000818:Animals; D000941:Antigens / Q000276:immunology; D004731:Endotoxins; D004926:Escherichia coli; D005334:Fever / Q000139:chemically induced; D006017:Glycolipids / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D006461:Hemolysis; D007928:Lethal Dose 50; D008050:Lipid A / Q000276:immunology / Q000494:pharmacology* / Q000633:toxicity; D008262:Macrophage Activation; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008807:Mice, Inbred BALB C; D008809:Mice, Inbred C3H; D008810:Mice, Inbred C57BL; D008938:Mitosis; D011817:Rabbits; D013154:Spleen / Q000166:cytology
D000941:Antigens; D004731:Endotoxins; D006017:Glycolipids; D008050:Lipid A; C044283:lipid X