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Lipid A: Relationships of Chemical Structure and Biological Activity

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Immunobiology and Immunopharmacology of Bacterial Endotoxins

Part of the book series: University of South Florida International Biomedical Symposia Series ((EMISS,volume 18))

Abstract

Thirty years ago in 1954, we summarized our knowledge then of the chemistry and biology of endotoxins (73). At that time, the phenol/water extraction procedure had been established (74), and the extracts from a number of bacterial strains studied chemically and biologically. These investigations had led to the identification of the extracted products as the 0 antigens and endotoxins of these bacteria, resembling products isolated earlier by Boivin and Mesrobeanu (2), Morgan et al. (44), Goebel et al. (15), Shear et al. (62), and others. It had been recognized that endotoxins are composed of a polysaccharide component linked covalently to a lipid component, and thus were chemically lipopolysaccharides. The lipid had been termed lipid A (73) and found to contain D - glucosamine, phosphate, and long-chain fatty acids in ester and amide linkages. It had been shown that the linkage of the polysaccharide to lipid A could be cleaved by hydrolysis with dilute acetic or hydrochloric acid, leading to free water-soluble polysaccharide and free water-insoluble lipid A. Neither free polysaccharide nor free insoluble lipid A expressed endotoxic activities. Nevertheless, it has been anticipated that lipid A was the biologically active part and that activity would result from the binding of lipid A to the polysaccharide component, the latter functioning as a hydrophilic carrier for lipid A.

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References

  1. L. Anderson and M. A. Nashed, The convergent approach to the synthesis of lipid A and its analogs, Am. Chem. Soc. Symp. Series 231: 255 (1983).

    CAS  Google Scholar 

  2. A. Boivin and L. Mesrobeanu, Recherches sur les antigenes somatiques et sur les endotoxines des bacteries. 1. Considerations generales et expose des techniques utilisees, Rev. Immunol. 1: 553 (1935).

    CAS  Google Scholar 

  3. D. Charon, C. Diolez, M. Mondange, S. R. Sarfati, L. Szabo, P. Szabo, and F. Trigalo, Synthetic studies on structural elements of the hydrophobic region present in bacterial endotoxins, Am. Chem. Soc. Symp. Series 231: 301 (1983).

    CAS  Google Scholar 

  4. R. Christian, G. Schulz, and F. M. Unger, Zur Struktur der 3-desoxyoctuloson-(KD0)-region des lipopolysaccharids von Salmonella minnesota R595, Tetrahyd. Lett 25: 3433 (1984).

    Article  CAS  Google Scholar 

  5. C. Galanos, Physical state and biological activity of lipopolysaccharides. Toxicity and immunogenicity of the lipid A component, Z. Immun. Forsch. 149: 214 (1975).

    CAS  Google Scholar 

  6. C. Galanos, M. Freudenberg, S. Hase, F. Jay, and E. Ruschmann, Biological activities and immunological properties of lipid A, in: “Microbiology 1977, ” D. Schlessinger, ed., American Society of Microbiology, Washington, D.C. (1977).

    Google Scholar 

  7. C. Galanos, M. A. Freudenberg, O. Lüderitz, E.Th. Rietschel, and O. Westphal, Chemical, physicochemical and biological properties of bacterial lipopolysaccharides, in: “Biomedical Applications of the Horseshoe Crab (Limulidae),” Alan R. Liss, Inc., New York (1979).

    Google Scholar 

  8. C. Galanos, M. A. Freudenberg, F. Jay, and D. Nerkar, Immunogenic properties of lipid A, Rev. Infect. Dis. 6: 546 (1984).

    Article  CAS  Google Scholar 

  9. C. Galanos, V. Lehmann, O. Lüderitz, E.Th. Rietschel, O. Westphal, H. Brade, L. Brade, M. A. Freudenberg, T. Hansen-Hagge, Th. Lüderitz, G. McKenzie, U. Schade, W. Strittmatter, K. Tanamoto, U. Zähringer, M. Imoto, H. Yoshimura, M. Yamamoto, T. Shimamoto, S. Kusumoto, and T. Shiba, Endotoxin properties of chemically synthesized lipid A part structures. Comparison of synthetic lipid A precursor and synthetic analogues with biosynthetic lipid A precursor and free lipid A, Eur. J. Biochem 140: 221 (1984).

    Article  PubMed  CAS  Google Scholar 

  10. C. Galanos, O Lüderitz, O Westphal, H. Brade, L. Brade, M. Frudenberg, U. Schade, M. imoto, H. Yoshimura, S. Kusumoto, and T. Shiba, Synthetic and natural Escherichia coli free lipid A express indentical endotoxic activities, Eur. J.Biochem. in press

    Google Scholar 

  11. C. Galanos, E.Th. Rietschel, O. Lüderitz, O. Westphal, B. Kim, and D. W. Watson, Biological activities of lipid A complexed with bovine serum albumin, Eur. J. Biochem. 31: 230 (1972).

    Article  PubMed  CAS  Google Scholar 

  12. C. Galanos, T. Hansen-Hagge, V. lehmann, and O. Lüderritz, Comparison of two lipid A precursor molecules in their capcity to express the local Shwartzman phenomenon, Infect. immun. in press (1985).

    Google Scholar 

  13. J. Gmeiner, O. Lüderitz, and O. Westphal, Biochemical studies on lipopolysaccharides of Salmonella R mutants 6. Investigations on the structure of the lipid A component, Eur. Biochem 7: 370 (1969).

    Article  CAS  Google Scholar 

  14. J. Gmeiner, M. Simon, and O. Lüderitz, The linkage of phosphate groups and of 2-keto-3-deoxyoctonate to the lipid A component in a Salmonella minnesota lipopolysaccharide, Eur. J.Biochem. 21: 355 (1971).

    Article  PubMed  CAS  Google Scholar 

  15. W. F. Goebel, F. Binkley, and E. Perlman, Studies on the Flexner group of dysentery bacilli I. The specific antigens of Shigella paradysenteriae (Flexner), J. Exp. Med. 81: 315 (1945).

    Article  PubMed  CAS  Google Scholar 

  16. Th. Hansen-Hagge, Entwicklung und Anwendung neuer Selektionsmetlioden zur Anreicherung von Salmonella Lipoid A Mutanten. Isolierung und Charakterisierung einer neuen Vorstufe, Thesis University of Freiburg (1984).

    Google Scholar 

  17. Th. Hansen-Hagge, V. Lehmann, and O. Lüderitz, free flow electrophoresis as a tool for enrichment of mutants with temperature dependent lethal mutations in lipid A synthesis, Eur. J. Biochem. in press. (1985)

    Google Scholar 

  18. T. Hasen-Hagge, V. Lehmann, U. Seydel, B. Lindner, and U. Zähringer, Isolation and structural analysis of two lipid A precursors from a KDO deficient mutant of Samonella typhimurium which differ in their hexadecanoic acid content, Arch. Microbiol. in press (1985).

    Google Scholar 

  19. M. Imoto, S. Kusumoto, T. Shiba, H. Naoki, T. Iwashita, E.Th. Rietschel, H. W. Wollenweber, C. Galanos, and 0. Lüderitz, Chemical structure of coli lipid A: linkage site of acyl groups in the disaccharide backbone, Tetrahedron Lett. 24: 4107 (1983).

    Article  Google Scholar 

  20. M. Imoto, H. Yoshimura, S. Kusumoto, and T. Shiba, Total synthesis of lipid A, the active principle of bacterial endotoxin, Proc. Japan Acad. 60B: 285 (1984).

    Article  CAS  Google Scholar 

  21. M. Imoto, H. Yoshimura, M. Yamamoto, T. Shimamoto, S. Kusumoto, and T. Shiba, Chemical synthesis of phosphorylated tetraacyl disaccharide corresponding to a biosynthetic precursor of lipid A, Tetrahedron Lett. 25: 2667 (1984).

    Google Scholar 

  22. M. Inage, H. Chaki, S. Kusumoto, and T. Shiba, Synthesis of liposaccharide corresponding to fundamental structure of Salmonella-type lipid A, Tetrahedron Lett. 21: 3889 (1980).

    Article  CAS  Google Scholar 

  23. M. Inage, H. Chaki, S. Kusumoto, and T. Shiba, Chemical synthesis of phosphorylated fundamental structure of lipid A, Tetrahedron Lett. 22: 2281 (1981).

    Article  CAS  Google Scholar 

  24. S. Kanegasaki, Y. Kojima, M. Matsuura, J,Y. Homma, A. Yamamoto, Y. Kumazawa, K. Tanamoto, T. Yasuda, T. Tsumita, M. Imoto, H. Yoshimura, M. Yamamoto, S. Shimamoto, and T. Shiba, Biological activities of analogues of lipid A based chemically on the revised structural model: comparison of mediator inducing, immunomodulating and endotoxic activities, Eur. Biochem 143: 237 (1984).

    Article  CAS  Google Scholar 

  25. S. Kanegasaki, T. Yasuda, T. Smumita, T. Tadakuma, J. Y. Homma, S. Kusumoto, and T. Shiba, Biological activities of synthetic lipid A analogues in artificial membrane vesicles, in: “Bacterial Endotoxins: Chemical, Biological, and Clinical Aspects,” J. Y. Homma, S. Kanegasaki, O. Lüderitz, T. Shiba, and O. Westphal, eds., Verlag Chemie, Weinheim (1984).

    Google Scholar 

  26. N. Kasai, K. Egawa, J. Mashimo, T. Shiba, and S. Kusumoto, Shwartzman activities of synthetic lipid A analogues and their effects on hepatic enzyme activities, in: “Bacterial Endotoxins: Chemical, Biological, and Clinical Aspects,” J. Y. Homma, S. Kanegasaki, O. Lüderitz, T. Shiba, and O. Westphal, eds., Verlag Chemie, Weinheim (1984).

    Google Scholar 

  27. M. Kiso and A. Hasegawa, Synthetic studies on lipid A and related compounds, in: “Bacterial Endotoxins: Chemical, Biological, and Clinical Aspects,” J. Y. Homma, S. Kanegasaki, O. Liideritz, T. Shiba, and O. Westphal, eds., Verlag Chemie, Weinheim (1984).

    Google Scholar 

  28. M. Kiso, H. Ishida, and A. Hasegawa, Synthesis of biologically active, novel monosaccharide analogs of lipid A, Agric. Biol, Chem. 48: 251 (1984).

    CAS  Google Scholar 

  29. S. Kotani, H. Takada, M. Tsujimoto, T. Ogawa, Y. Mori, N. Sakuta, A. Kawasaki, M. Inage, S. Kusumoto, T. Shiba, and N, Kasai, 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. 41: 758 (1983).

    PubMed  CAS  Google Scholar 

  30. S. Kotani, H. Takada, M. Tsujimoto, T. Ogawa, K. Harada, Y. Mori, A. Kawasaki, A. Tanaka, S. Nagao, 0. Tanaka, T. Shiba, S. Kusumoto, M. Imoto, H. Yoshimura, M. Yamamoto, and T. Shimamoto, Immunologically active lipid A analogs synthesized according to revised structural model of natural lipid A, Infect. Immun. 45: 293 (1984).

    PubMed  CAS  Google Scholar 

  31. Y. Kumazawa, M. Matsuura, Y. Nakatsuru-Watanabe, M. Fukumoto, C. Nischimura, J. Y. Homma, M. Inage, S. Kusumoto, and T. Shiba, Mitogenic and polyclonal B cell activation activities of synthetic lipid A analogues, Eur. J. Immunol. 14: 109 (1984).

    Article  PubMed  CAS  Google Scholar 

  32. Y. Kumazawa, M. Matsuura, J. Y. Homma, Y. Nakatsuru, M. Kiso, and A. Hasegawa, B cell activation and adjuvant activities of chemically synthesized analogues of nonreducing sugar moiety of lipid A, Eur. J. Immunol. 15: 199 (1985).

    Article  PubMed  CAS  Google Scholar 

  33. S. Kusumoto, M. Yamamoto, and T. Shiba, Chemical synthesis of lipid X and lipid Y, acyl glucosamine-l-phosphates isolated from Escherichia coli mutants, Tetrahedron Lett. 25: 3727 (1984).

    Article  CAS  Google Scholar 

  34. V. Lehmann, Isolation, purification and properties of an intermediate in 3-deoxy-D-manno-octulosonic acid - lipid A biosynthesis, Eur. J. Biochem. 75: 257 (1977).

    Article  PubMed  CAS  Google Scholar 

  35. V. Lehmann, E. Rupprecht, and M. J. Osborn, Isolation of mutants conditionally blocked in the biosynthesis of the 3-deoxy-D-manno-octulosonic acid - lipid A part of lipopolysaccharides derived from Salmonella typhimurium Eur. J. Biochem. 76: 41 (1977).

    Article  PubMed  CAS  Google Scholar 

  36. O. Lüderitz, C. Galanos, V. Lehmann, H. Mayer, E.Th. Rietschel, and J. Weckesser, Chemical structure and biological activities of lipid A’s from various bacterial families, Naturwissenschaften 65: 575 (1978).

    Article  Google Scholar 

  37. O. Lüderitz, K. Tanamoto, C. Galanos, O. Westphal, U. Zahringer, E.Th. Rietschel, S. Kusumoto, and T. Shiba, Structural principles of lipopolysaccharides and biological properties of synthetic partial structures, American Chemical Society Symposium Series 231: 3 (1983).

    Google Scholar 

  38. O. Lüderitz, O. Westphal, A. M. Staub, and L. LeMinor, Preparation and immunological properties of an artificial antigen with colitose (3-deoxyl-L-fucose) as determinant group, Nature 188: 556 (1960).

    Article  PubMed  Google Scholar 

  39. M. Matsuura, Y. Kojima, J. Y. Homma, Y. Kumazawa, Y. Kubota, T. Shiba, and S. Kusumoto, Biological activities of synthetic lipid A analogues, in: “Bacterial Endotoxins: Chemical, Biological, and Clinical Aspects”, J. Y. Homma, S. Kanegasaki, O. Luderitz, T. Shiba, and O. Westphal, eds., Verlag Chemie, Weinheim (1984).

    Google Scholar 

  40. M. Matsuura, Y. Kojima, J. Y. Homma, Y. Kubota, N. Shibukawa, M. Shibata, M. Inage, S. Kusumoto, and T. Shiba, Interferon-inducing, pyrogenic and proclotting enzyme of horseshoe crab activities of chemically synthesized lipid A analogues, Eur. J. Biochem 137: 639 (1983).

    Article  PubMed  CAS  Google Scholar 

  41. M. Matsuura., Y. Kojima, Y. Homma, Y. Kubota, A. Yamamoto, M. Kiso, and A. Hasegawa, Biological activities of chemically synthesized analogues of the nonreducing sugar moiety of lipid A, FEBS Lett. 167: 226 (1984).

    Article  PubMed  CAS  Google Scholar 

  42. H. Mayer, P. V. Salimath, O. Hoist, and J. Weckesser, Unusual lipid A types in phototrophic bacteria and related species, Rev. Infect. Dis. 6: 542 (1984).

    Article  PubMed  CAS  Google Scholar 

  43. H. Mayer and J. Weckesser, Unusual lipid Afs: structures, taxonomic relevance and potential value for endotoxin research, in: “Handbook of Endotoxins, Volume 1: Chemistry of Endotoxin,” E.Th. Rietschel, ed., Elsevier, Amsterdam, New York, and Oxford (1984).

    Google Scholar 

  44. W. T. J. Morgan and S. M. Partridge, Studies on immunochemistry. 4. The fractionation and nature of antigenic material isolated from bacterium dysenteriae (Shiga), J. Biochem. 34: 169 (1940).

    CAS  Google Scholar 

  45. C. A. Mulford and M. J. Osborn, An intermediate step in translocation of lipopolysaccharide to outer membrane of Salmonella typhimurium, Proc. Natl. Acad. Sci. USA 80: 1159 (1983).

    Article  PubMed  CAS  Google Scholar 

  46. R. S. Munson, N. S. Rasmussen, and M. J. Osborn, Biosynthesis of Lipid A. Enzymatic incorporation of 3-deoxy-P-mannooctulosonate into a precursor of lipid A in Salmonella typhimurium, J. Biol. Chem. 253: 1503 (1978).

    PubMed  CAS  Google Scholar 

  47. M. N. Nashed and L. Anderson, A convergent and flexible approach to the synthesis of enterobacterial lipid A. Fully substituted disaccharides having palmitoyl as fatty acyl moiety, Carboh. Res. 92: C5 (1981).

    Article  CAS  Google Scholar 

  48. A. Nowotny, Chemical structure of a phosphomucolipid and its occurrence in some strains of Salmonella, J. Chem. Soc 83: 501 (1961).

    Article  CAS  Google Scholar 

  49. A. Nowotny, Heterogeneity of endotoxins, in: “Handbook of Endotoxins, Volume 1: Chemistry of Endotoxin,” E.Th. Rietschel, ed., Elsevier, Amsterdam, New York and Oxford (1984).

    Google Scholar 

  50. M. J. Osborn, Biosynthesis and assembly of lipopolysaccharide of the outer membrane, in: “Bacterial Outer Membranes, Biogenesis, and Functions,” M. Inouye, ed., John Wiley and Sons, New York (1979).

    Google Scholar 

  51. M. Schindler, M. J. Osborn, and D. E. Koppel, Lateral diffusion of LPS in the outer membrane of S. typhimurium, Nature 285: 261 (1980).

    Article  PubMed  CAS  Google Scholar 

  52. N. Quereshi, K. Takayama, D. Heller, and C. Fenselau, Position of ester groups in the lipid A backbone of lipopolysaccharides obtained from Salmonella typhimurium, J. Biol. Chem 258: 12947 (1983).

    Google Scholar 

  53. Ch.R. H. Raetz, The enzymatic synthesis of lipid A: molecular structure and biological function of monosaccharide precursors, Rev. Infect. Dis. 6: 463 (1984).

    Article  CAS  Google Scholar 

  54. Ch.R. H. Raetz, Escherichia coli mutants that allow elucidation of the precursors and biosynthesis of lipid A, in: “Handbook of Endotoxins, Volume 1: Chemistry of Endotoxin,” E.Th. Rietschel, ed., Elsevier, Amsterdam, New York and Oxford (1984).

    Google Scholar 

  55. B. L. Ray, G. Painter, and Ch.R. H. Raetz, The biosynthesis of gram-negative endotoxin. Formation of lipid A disaccharides from monosac-charide precursors in extracts of Escherichia coli, J. Biol. Chem. 259: 4852 (1984).

    PubMed  CAS  Google Scholar 

  56. E.Th. Rietschel, H. Gottert, 0. Luderitz, and 0. Westphal, Nature and linkages of the fatty acids present in the lipid A component of Salmonella lipopolysaccharides, Eur. J. Biochem 28: 166 (1972).

    Article  PubMed  CAS  Google Scholar 

  57. E.Th. Rietschel, Z. Sidorczyk, U. Zahringer, H.-W. Wollenweber, and O. Luderitz, Analysis of the primary structure of lipid A, in: “Bacterial Lipopolysaccharides, Structure, Synthesis, and Biological Activities”, American Chemical Society Symposium Series 231:195 (1983).

    Chapter  Google Scholar 

  58. E.Th. Rietschel, H.-W. Wollenweber, H. Brade, U. Zahringer, B. Lindner, U. Seydel, H. Bradaczek, G. Barnickel, H. Labischinski, and P. Giesbrecht, Structure and conformation of the lipid A component of lipopolysaccharides, in: “Handbook of Endotoxins, Volume 1: Chemistry of Endotoxin,” E.Th. Rietschel, ed., Elsevier, Amsterdam, New York and Oxford (1984).

    Google Scholar 

  59. E.Th. Rietschel, H.-W. Wollenweber, R. Russa, H. Brade, and U. Zahringer, Concepts of the chemical structure of lipid A, Rev. Infect. Dis. 6: 432 (1984).

    Article  CAS  Google Scholar 

  60. M. R. Rosner, H. G. Khorana, and A. C. Satterthwait, The structure of lipopolysaccharide from a heptoseless mutant of Escherichia coli K-12. II. The application of P NMR spectroscopy, J. Biol. Chem. 254: 5918 (1979).

    CAS  Google Scholar 

  61. U. Seydel, B. Lindner, H.-W. Wollenweber, and E.Th. Rietschel, Structural studies on the lipid A component of enterobacterial lipopolysaccharides by laser desorption mass spectrometry. Location of acyl groups at the lipid A backbone, Eur. Biochem. 145: 505 (1984).

    Article  CAS  Google Scholar 

  62. M. J. Shear and F. C. Turner, Chemical treatment of tumors. V. Isolation of the hemorrhage producing fraction from Serratia Marcescens (Bacillus prodigiosus) culture filtrate, J. Natl. Cancer Inst. 4: 81 (1943).

    CAS  Google Scholar 

  63. T. Shiba, S. Kusumoto, M. Inage, H. Chaki, M. Imoto, and T. Shimamoto, How can chemical synthesis approach the entity of lipid A, in: “Bacterial Endotoxins: Chemical, Biological, and Clinical Aspects,” J. Y. Homma, S. Kanegasaki, O. Lüderitz, T. Shiba, and O. Westphal, eds., Verlag Chemie, Weinheim (1984).

    Google Scholar 

  64. Z. Sidorezyk, U. Zähringer, and E.Th. Rietschel, Chemical structure of the lipid A component of the lipopolysaccharide from a Proteus miralilis re-mutant, Eur. J. Biochem. 137: 15 (1983).

    Article  Google Scholar 

  65. S. M. Strain, S. W. Fesik, and I. M. Armitage, Characterization of lipo- polysaccharide from a heptoseless mutant of Escherichia coli by carbon 13 nuclear magnetic resonance, J. Biol. Chem. 258: 2906 (1983).

    PubMed  CAS  Google Scholar 

  66. K. Takayama, N. Qureshi, and P. Mascagni, Complete structure of lipid A obtained from the lipopolysaccharides of the heptoseless mutant of Salmonella typhimurium J. Biol. Chem. 258: 12801 (1983).

    PubMed  CAS  Google Scholar 

  67. K. Takayama, N. Qureshi, P. Mascagni, M. A. Nashed, L. Anderson, and Ch.R. H. Raetz, Fatty acyl derivatives of glucosamine 1-phosphate in Escherichia coli and their relation to lipid A. Complete structure of a diacyl GlcN-l-P found in a phosphatidylglycerol-deficient mutant, J. Biol. Chem. 258: 7379 (1983).

    PubMed  CAS  Google Scholar 

  68. K. Tanamoto, C. Galanos, O. Lüderitz, S. Kusumoto, and T. Shiba, Mitogenic activities of synthetic lipid A analogus and suppression of mitogenicity of lipid A, Infect. Immun. 44: 427 (1984).

    PubMed  CAS  Google Scholar 

  69. K. Tanamoto, U. Zähringer, G. R. McKenzie, C. Galanos, E.Th. Rietschel, O. Lüderitz, S. Kusumoto, and T. Shiba, Biological activities of synthetic lipid A analogs: Pyrogenicity, lethal toxicity, anticomplement activity, and induction of gelation of Limulus amoebocyte lysate, Infect. Immun. 44: 421 (1984).

    PubMed  CAS  Google Scholar 

  70. S. N. Vogel, G. S. Madonna, L. M. Wahl, and P. D. Rich, In vitro stimulation of C3H/HeJ spleen cells and macrophages by a precursor molecule derived from Salmonella typhimurium, J. Immunol. 132:347 (1983).

    Google Scholar 

  71. P. Waldstätten, R. Christian, G. Schulz, F. M. Unger, P. Kosma, C. Kratky, and H. Paulsen, Synthesis of oligosaccharides containing 3-deoxy-D-manno-2-octulopyranosylono (KD0) residues, American Chemical Society Symposium Series, 231: 121 (1983).

    Google Scholar 

  72. J. Weckesser, G. Drews, and H. Mayer, Lipopolysaccharides of photosynthetic prokaryotes, Ann. Rev. Microbiol 33: 215 (1979).

    Article  CAS  Google Scholar 

  73. O. Westphal and O. Lüderitz, Chemische Erforschung von Lipopolysac- chariden gramnegativer Bakterien, Angew. Chemie. 66: 407 (1954).

    Article  CAS  Google Scholar 

  74. O. Westphal, 0. Lüderitz, and F. Bister, Ober die Extraktion von Bakterien mit phenol/wasser, Z. Naturf 7b: 148 (1952).

    Google Scholar 

  75. H.-W. Wollenweber, K. W. Broady, O. Lüderitz, and E.Th. Rietschel, The chemical structure of lipid A: demonstration of amide-linked 3-acyloxyacyl residues in Salmonella minnesota re lipopolysaccharides, Eur. J. Biochem 124: 191 (1982).

    Article  PubMed  CAS  Google Scholar 

  76. H.-W. Wollenweber, U. Seydel, B. Lindner, O. Lüderitz, and E.Th. Rietschel, Nature and location of amide-bound (R)-3-acyloxyacyl groups in lipid A of lipopolysaccharides from various gram-negative bacteria, Eur. J. Biochem 145: 265 (1984).

    Article  PubMed  CAS  Google Scholar 

  77. T. Yasuda, Sh. Kanegasaki, T. Tsumita, T. Tadakuma, J. Y. Homma, M. Inage, S. Kusumoto, and T. Shiba, Biological activity of chemically synthesized lipid A analogues. Demonstration of adjuvant effect in haptensensitized liposomal system, Eur. J. Biochem. 124: 405 (1982).

    Article  PubMed  CAS  Google Scholar 

  78. T. Yasuda, S. Kanegasaki, T. Tsumita, T. Tadakuma, N. Ikewaki, J. Y. Homma, M. Inage, S. Kusumoto, and T. Shiba, Further study of biological activities of chemically synthesized analogues of lipid A in artificial membrame vesicles, Eur. J. Biochem. 140: 245 (1984).

    Article  PubMed  CAS  Google Scholar 

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  1. Max-Planck Institut für Immunobiologie, Freiburg and Forschungsinstitut Borstel, Borstel, Federal Republic of Germany

    Otto Lüderitz, Chris Galanos, Ernst Th. Rietschel & Otto Westphal

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  1. Otto Lüderitz
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  1. University of South Florida College of Medicine, Tampa, Florida, USA

    Andor Szentivanyi (Dean of the College of Medicine Deputy Vice President for Medical Affairs Professor of Pharmacology and Internal Medicine Chairman of the Department of Pharmacology and Therapeutics) & Herman Friedman (Professor and Chairman) (Dean of the College of Medicine Deputy Vice President for Medical Affairs Professor of Pharmacology and Internal Medicine Chairman of the Department of Pharmacology and Therapeutics) &  (Professor and Chairman)

  2. University of Pennsylvania, Philadelphia, Pennsylvania, USA

    Alois Nowotny

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Lüderitz, O., Galanos, C., Rietschel, E.T., Westphal, O. (1986). Lipid A: Relationships of Chemical Structure and Biological Activity. In: Szentivanyi, A., Friedman, H., Nowotny, A. (eds) Immunobiology and Immunopharmacology of Bacterial Endotoxins. University of South Florida International Biomedical Symposia Series, vol 18. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2253-5_5

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