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. 1984 Jul;45(1):293–296. doi: 10.1128/iai.45.1.293-296.1984

Immunobiologically active lipid A analogs synthesized according to a revised structural model of natural lipid A.

S Kotani, H Takada, M Tsujimoto, T Ogawa, K Harada, Y Mori, A Kawasaki, A Tanaka, S Nagao, S Tanaka, et al.
PMCID: PMC263318  PMID: 6735470

Abstract

Synthetic lipid A analogs which have two amide-bound and two ester-bound (R)-3-hydroxytetradecanoyl groups at the C-2 and -2' and C-3 and -3' positions of beta(1-6)glucosamine disaccharide mono- or diphosphates showed high activities in most in vitro assays, and the lethality of a diphosphate derivative to galactosamine-treated mice was almost comparable to that of natural lipid A. The pyrogenicity and Shwartzman induction activity of the synthetic analogs, however, were much less than those of natural lipid A.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Galanos C., Freudenberg M. A., Reutter W. Galactosamine-induced sensitization to the lethal effects of endotoxin. Proc Natl Acad Sci U S A. 1979 Nov;76(11):5939–5943. doi: 10.1073/pnas.76.11.5939. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Galanos C., Lüderitz O. Electrodialysis of lipopolysaccharides and their conversion to uniform salt forms. Eur J Biochem. 1975 Jun;54(2):603–610. doi: 10.1111/j.1432-1033.1975.tb04172.x. [DOI] [PubMed] [Google Scholar]
  3. Kotani S., Takada H., Tsujimoto M., Ogawa T., Mori Y., Sakuta M., Kawasaki A., Inage M., Kusumoto S., Shiba T. Immunobiological activities of synthetic lipid A analogs and related compounds as compared with those of bacterial lipopolysaccharide, re-glycolipid, lipid A, and muramyl dipeptide. Infect Immun. 1983 Aug;41(2):758–773. doi: 10.1128/iai.41.2.758-773.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Lehmann V. Isolation, purification and properties of an intermediate in 3-deoxy-D-manno-octulosonic acid--lipid A biosynthesis. Eur J Biochem. 1977 May 2;75(1):257–266. doi: 10.1111/j.1432-1033.1977.tb11525.x. [DOI] [PubMed] [Google Scholar]
  5. Lüderitz O., Galanos C., Rietschel E. T. Endotoxins of Gram-negative bacteria. Pharmacol Ther. 1981;15(3):383–402. doi: 10.1016/0163-7258(81)90051-6. [DOI] [PubMed] [Google Scholar]
  6. Nagao S., Tanaka A. Inhibition of macrophage DNA synthesis by immunomodulators. I. Suppression of [3H]thymidine incorporation into macrophages by MDP and LPS. Microbiol Immunol. 1983;27(4):377–387. doi: 10.1111/j.1348-0421.1983.tb00596.x. [DOI] [PubMed] [Google Scholar]
  7. Obayashi T., Kawai T., Tamura H., Nakahara C. New limulus amoebocyte lysate test for endotoxaemia. Lancet. 1982 Jan 30;1(8266):289–289. doi: 10.1016/s0140-6736(82)91016-9. [DOI] [PubMed] [Google Scholar]
  8. Strain S. M., Fesik S. W., Armitage I. M. Characterization of lipopolysaccharide from a heptoseless mutant of Escherichia coli by carbon 13 nuclear magnetic resonance. J Biol Chem. 1983 Mar 10;258(5):2906–2910. [PubMed] [Google Scholar]
  9. Takayama K., Qureshi N., Mascagni P., Nashed M. A., Anderson L., Raetz C. R. Fatty acyl derivatives of glucosamine 1-phosphate in Escherichia coli and their relation to lipid A. Complete structure of A diacyl GlcN-1-P found in a phosphatidylglycerol-deficient mutant. J Biol Chem. 1983 Jun 25;258(12):7379–7385. [PubMed] [Google Scholar]
  10. Tanaka A., Nagao S., Imai K., Mori R. Macrophage activation by muramyl dipeptide as measured by macrophage spreading and attachment. Microbiol Immunol. 1980;24(6):547–557. doi: 10.1111/j.1348-0421.1980.tb02858.x. [DOI] [PubMed] [Google Scholar]
  11. Westphal O., Jann K., Himmelspach K. Chemistry and immunochemistry of bacterial lipopolysaccharides as cell wall antigens and endotoxins. Prog Allergy. 1983;33:9–39. [PubMed] [Google Scholar]

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