title: Endotoxic properties of synthetic pentaacyl lipid A precursor Ib and a structural isomer.
abstract: 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.
authors.affiliation: Institut für Experimentelle Biologie und Medizin, Forschungsinstitut Borstel, Federal Republic of Germany.
authors.forename: E T
authors.initials: ET
authors.lastname: Rietschel
authors.forename: L
authors.initials: L
authors.lastname: Brade
authors.forename: U
authors.initials: U
authors.lastname: Schade
authors.forename: C
authors.initials: C
authors.lastname: Galanos
authors.forename: M
authors.initials: M
authors.lastname: Freudenberg
authors.forename: O
authors.initials: O
authors.lastname: Lüderitz
authors.forename: S
authors.initials: S
authors.lastname: Kusumoto
authors.forename: T
authors.initials: T
authors.lastname: Shiba
mesh_terms: 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
chemical_list: D000941:Antigens; D004731:Endotoxins; D006017:Glycolipids; D008050:Lipid A; C044283:lipid X