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Bacterial Lipopolysaccharides: Relationship of Structure and Conformation to Endotoxic Activity, Serological Specificity and Biological Function

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Endotoxin

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 256))

Abstract

Gram-negative bacteria express in their cell envelope various amphiphilic macromolecules among which the lipopolysaccharides (LPS) are of special significance for bacterial viability and the interaction of bacteria with host organisms. Together with phospholipids and proteins, lipopolysaccharides form the outer membrane of gram-negative bacteria. This outer membrane has an asymmetric architecture, i.e., lipopolysaccharides are located exclusively in the outer leaflet through which the bacterial cell interacts with its environment.

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References

  1. Brade, H., Brade, L., and E. Th. Rietschel, 1988, Structure-activity relationships of bacterial lipopolysaccharides (endotoxins). Zbl. Bakt. Hyg. A 268: 151–179.

    Google Scholar 

  2. Brade, L., Brandenburg, K., Kuhn, H.-M., Kusumoto, S., Macher, I., Rietschel, E. Th., and Brade, H., 1987, The immunogenicity and antigeni-city of lipid A are influenced by its physicochemical state and environment. Infect. Immun. 55: 2636–2644.

    Google Scholar 

  3. Brandenburg, K., and Seydel, U., 1984, Physical aspects of structure and function of membranes made from lipopolysaccharides and free lipid A. Biochem. Biophys. Acta 775: 225–238.

    Google Scholar 

  4. Caroff, M., Lebbar, S., and Szabo, L., 1987, Detection of 3-deoxy-2octulosonic acid in thiobarbiturate-negative endotoxins. Carb. Res. 161: C4 - C7.

    Article  Google Scholar 

  5. Chaby, R., Charon, D., Pedron, T., and Girard, R., 1987, Antigenic determinants of lipid A analyzed with synthetic models and monoclonal antibodies. Biochem. Biophys. Res. Commun. 143: 723–731.

    Google Scholar 

  6. Chaby, R. and Szabo, L., 1975. 3-Deoxy-2-octulosonic acid 5-phosphate: a component of the endotoxin of Bordetella pertussis, Eur. J. Biochem. 59: 277–280.

    Google Scholar 

  7. Galanos, C., Luderitz, 0., Freudenberg, M. A., Brade, L., Schade, U., Rietschel, E. Th., Kusumoto, S., and Shiba, T., 1986, Biological activity of synthetic heptaacyl lipid A representing a component of Salmonella minnesota R595 lipid A. Eur. J. Biochem. 160: 55–59.

    Google Scholar 

  8. Galânos, C., Luderitz, 0., Rietschel, E. Th., and Westphal, 0., 1977, Newer aspects of the chemistry and biology of bacterial lipopolysaccharides, with special reference to their lipid A component, in: “International Review of Biochemistry, Biochemistry of Lipids IÌ,” T. W. Goodwin, ed., University Park Press, Baltimore 14: 239–335.

    Google Scholar 

  9. Haselberger, A., Hildebrandt, J., Lam, C., Liehl, E., Loibner, H., Macher, I., Rosenwirth, B., Schutze, E. Vyplel, H. and Unger, F. M. 1987, Immunopharmacology of lipopolysaccharides (endotoxins) from gram-negative bacteria. Triangle, Sandoz Journal of Medical Science 26: 33–49.

    Google Scholar 

  10. Helander, I., Lindner, B., Brade, H., Altmann, K., Lindberg, A. A., Rietschel, and Zahringer, U., 1988, Chemical structu~b+f the lipopoly-saccharide of Haemophilus influenzae strain I-69 Rd. Description of a novel deep rough chemotype. Eur. J. Biochem. 177: 483–492.

    Google Scholar 

  11. Hitchcock, P., Leive, L., Makela, P. H., Rietschel, E. Th., Strittmatter, W. and Morris, D., 1986, Lipopolysaccharide nomenclature–past, present and future. J. Bacteriol. 166: 699–705.

    PubMed  CAS  Google Scholar 

  12. Home, J. Y., Matsuura, M., Kanegasakai, S. Kawakubo, Y., Kojima, Y., Shibukawa, N., Kumazawa, Y., Yamamoto, A., Tanamoto, K., Yasuda, T., Imoto, M., Yoshimura, H., Kusumoto, S., and Shiba, T., 1985, Structural requirements of lipid A responsible for the functions: a study with chemically synthesized lipid A and its analogues. J. Biochem. ( Tokyo ) 98: 395–406.

    Google Scholar 

  13. Imoto, M., Yoshimura, H., Shimamoto, T., Sakaguchi, N., Kusumoto, S., and Shiba, T., 1987, Total synthesis of Escherichia coli lipid A, the endotoxically active principle of cell-surface lipopolysaccharide. Bull. Chem. Soc. Jpn. 60: 2205–2214.

    Google Scholar 

  14. Israelachvili, J. N., Marcelja, S., and Horn, R. G., 1980, Physical principles of membrane organization. Quart. Rev. Biophys. 13: 121–200.

    Google Scholar 

  15. Jacobs, D., 1984, Structural features of binding of lipopolysaccharides to murine lymphocytes. Rev. Infect. Dis. 6: 501–505.

    Google Scholar 

  16. Kaca, W., Brade, L., Rietschel, E. Th., and Brade, H., 1986, The effect of removal of D-fructose on the antigenicity of the lipopolysaccharide from a rough mutant of Vibrio cholerae OGAWA. Carb. Res. 149: 293–298.

    Google Scholar 

  17. Kanegasaki, S., Tanamoto, K., Yasuda, T., Homma, J. Y., Matsuura, M. Nakatsuka, M., Kumazawa, Y., Yamamoto, A., Shiba, T., Kusumoto, S., Imoto. M. Yoshimura, A., and Shimamoto, T., 1986, Structure-activity relationship of lipid A: Comparison of_biological activities of natural and synthetic lipid A’s with different fatty acid compositions. J. Biochem. ( Tokyo ) 99: 1203–1210.

    Google Scholar 

  18. Kasai, N., Arata, S., Mashimo, J.-I. Okuda, K., Aihara, Y., Kotani, S., Takada, H., Shiba, T., Kusumoto, S., Imoto, M., Yoshimura, H., and Shimamoto, T., 1986, Synthetic Salmonella-type lipid A with high serological specificity. Infect. Immun. 51: 43–48.

    Google Scholar 

  19. Kawahara, K., Brade, H., Rietschel, E. Th., and Zahringer, U., 1987, Studies on the chemical structure of the core-lipid A region of the lipopolysaccharide of Acinetobacter calcoaceticus NCTC 10305. Detection of a new 2-octulosonic acid interlining the core oligosaccharide and lipid A component. Eur. J. Biochem. 163: 489–495.

    Google Scholar 

  20. Rondo, S., Iguchi, T., and Kisatsune, K., 1988, Occurrence of thiobarbituric acid test-positive substances in lipopolysaccharides (LPS) of Vibrionaceae. in: “Adv. Res. Cholera and Related Diarrheas,” Vol. 4: 71–76, KTK Scientific Publishers, Tokyo.

    Google Scholar 

  21. Rondo, S., Zahringer, U., Rietschel, E. Th., and Hisatsune, K., 1989, Isolation and identification of 3-deoxy-D-threo-hexulosonic acid as a constituent of the lipopolysaccharide of Vibrio parahaemolyticus serotypes 07 and 012. Carb. Res. in press.

    Google Scholar 

  22. Kotani, S., Takada, H., Tsujimoto, M., Ogawa, T., Takahashi, I., Ikeda, T., Otsuka, K., Shimanchi, H., Kasai. N., Mashimo, J., Nagao, S. Tanaka, S., Harada, K., Nagaki, K., Kitamura, H., Shiba, T., Kusumoto, S., Imoto, M., and Yoshimura, H., 1985, Synthetic lipid A with endotoxic and related biological activities comparable to those of a natural lipid A from an Escherichia coli Re-mutant. Infect. Immun. 49: 225–237.

    Google Scholar 

  23. Kumazawa, Y., Nakatsuka, M., Takimoto, H., Furuya, T., Nagumo, T., Yamamoto, A., Homma, J. Y., Inada, K., Yoshida, M., Kiso, M., and Hasegawa, A., 1988, Importance of fatty acid substituents of chemically synthesized lipid A-subunit analogs in the expression of immunopharmacological activity. Infect. Immun. 56: 149–155.

    Google Scholar 

  24. Labischinski, H., Barnickel, G., Bradaczek, H., Naumann, D., Rietschel, E. Th., and Giesbrecht, P., 1985, High state of order of isolated bacterial lipopolysaccharide and its possible contribution to the permeation barrier property of the outer membrane. J. Bacteriol. 162: 9–20.

    PubMed  CAS  Google Scholar 

  25. Luderitz, 0., Freudenberg, M. A., Galanos, C., Lehmann, V., Rietschel, E. Th., and Shaw, D. H., 1982. Lipopolysaccharides of gram-negative bacteria. in: “Membrane Lipids of Procaryotes. Current Topics in Membranes and Transport,” S. Razin and S. Rottem, eds. Academic Press, Inc., New York, pp. 79–151.

    Google Scholar 

  26. Mayer, H., and Weckesser, J., 1984, Unusual lipid A’s: structures taxonomical relevance and potential value for endotoxin research. in: “Handbook of Endotoxins,” R. Proctor, ed., Vol. 1, Chemistry of Endtoxin. E. Th. Rietschel, ed., Elsevier/North-Holland Biomedical Press, Amsterdam, pp. 221–247.

    Google Scholar 

  27. Moxon, E. R., 1985, Antigen expression influencing tissue invasion of Haemophilus influenza type B, in: “Bayer-Symposium VIII. The pathogenesis of bacterial infections,” G. G. Jackson and H. Thomas, eds. Springer Verlag, Berlin/Heidelberg, pp. 17–29.

    Google Scholar 

  28. Naumann, D., Schultz, C., Born, J., Labischinski, H., Brandenburg, K., von Busse, Brade, H., and Seydel. U., 1987. Investigations on the polymorphism of lipid A from lipopolysaccharides of Escherichia coli and Salmonella Minnesota by fourier-transform infrared spectroscopy. Eur. J. Biochem. 164: 159–169.

    Google Scholar 

  29. Nowotny, A., 1984, Heterogeneity of endotoxins, in: “Handbook of Endotoxins,” R. Proctor, ed., “Chemistry of Endotoxin, E. Th. Rietschel, ed. Vol. 1, Elsevier/North-Holland Biomedical Press, Amsterdam, pp. 308–338.

    Google Scholar 

  30. Proctor, R. A., ed., “Handbook of Endotoxins,” Vol. 1, Chemistry of Endotoxin, 1984; Vol. 2, Pathophysiology of endotoxin, 1985; Vol. 3, Cellular biology of endotoxin, 1985; Vol. 4, Clinical aspects of endotoxin shock, 1986, Elsevier/North-Holland Biomedical Press. Amsterdam.

    Google Scholar 

  31. Raetz, C., R., H., 1987, Structure and biosynthesis of lipid A, in: “Escherichia coli and Salmonella typhimurium. Cellular and molecular biology,” C. Neidhardt, J. L. Ingraham, K. Brooks Low, B. Magasanik, M. Schaechter, and H. E. Umbarger, eds. Am. Soc. Microbiol., Washington, D.C., pp. 498–503.

    Google Scholar 

  32. Rietschel, E. Th., Brade, H., Brade, L., Brandeburg, K., Schade, U. F., Seydel, U., Zahringer, U., Galanos, C. Luderitz, 0., Westphal. 0. Labischinski, H., Kusumoto, S., and Shiba, T., 1987, Lipid A, the endotoxic center of bacterial lipopolysaccharides: relation of chemical structure to biological activity. Prog. Clin. Biol. Res. 231: 25–53. (Alan R. Liss, New York) r

    Google Scholar 

  33. Rietschel, E. Th., Brade, L., Schade, U., Galanos, C., Freudenberg, M., Luderitz, 0., Kusumoto, S., and Shiba, T., 1987, Endotoxic properties of synthetic petaacyl lipid A precursor Ib and a structural isomer. Eur. J. Biochem. 169: 27–31.

    Google Scholar 

  34. Rietschel, E. Th., Brade, L., Schade, U. F., Seydel, U., Zahringer, U., and Brade, H., 1988, Bacterial endotoxins: properties and structure of biologically active domains, in: “Surface structures of microorganisms and their interaction with the é mammalian host,” E. Schrinner, M. Richmond, G. Seibert, and U. Schwartz, eds. Verlag Chemie, Weinheim, pp. 1–41.

    Google Scholar 

  35. Rietschel, E. Th., Wollenweber, H. W., Brade, H., Zahringer, U., Lindner,B., Seydel, U., Bradaczek, H., Barnickel, G., Labischinski, H., and Giesbrecht, P., 1984, Structure and conformation of the lipid A component of lipopolysaccharides, in: “Handbook of Endotoxins,” R. Proctor, ed., Vol. 1, “Chemistry of Endotoxins,” E. Th. Rietschel, ed, Elsevier, Amsterdam, New York, Oxford, pp. 187–220.

    Google Scholar 

  36. Shiba, T., and Kusumoto, S., 1984, Chemical synthesis and biological activity of lipid A analogs, in: “Handbook of Endotoxins,” R. Proctor, ed., Vol. 1, “Chemistry of Enaötoxin,” E. Th. Rietschel, ed. Elsevier, Amsterdam, New York, Oxford, pp. 284–302.

    Google Scholar 

  37. Tacken, A., Rietschel, E. Th., and Brade, H., 1986, Methylation analysis of the heptose/3-deoxy-D-manno-2-octulosonic acid region (inner core) of lipopolysaccharide from Salmonella minnesota rough mutants. Carbohydr. Res. 149: 279–291.

    Google Scholar 

  38. Takahashi, I., Kotani, S., Takada, H., Tsujimoto, M., Ogawa, T., Shiba, T., Kusumoto, S., Yamamoto, M., Hasegawa, A., Kiso, M., Nishijima, M., Amano, F., Akamatsu, Y., Harada, K., Tanaka, S., Okamura, H. and Tamura, T., 1987, Requirement of a properly acylated (1–6)-D-glucosamine disac- charide bisphosphate structure for efficient manifestation of full endotoxic and associated bioactivities of lipid A. Infect. Immun. 65: 57–68.

    Google Scholar 

  39. Takayama, K., Quereshi, N., Hyver, K., Honovich, J. Cotter, R. J., Mascagni, P., and Schneider. H. 1986, Characterization of a structural series of lipid A obtained from the lipopolysaccharides of Neisseria gonorrhoeae. J. Biol. Chem. 261: 10624–10631.

    Google Scholar 

  40. Vaara, M., and Nikaido, H., 1984. Molecular organization of bacterial outer membrane, in: “Handbook of Endotoxins,” R. Proctor, ed., Vol. 1, “Chemistry of Endotoxin,” E. Th. Rietschel, ed. Elsevier, Amsterdam, New York, Oxford, pp. 1–45.

    Google Scholar 

  41. van Alphen, L., Lugtenberg, B., Rietschel, E. Th., and Mombers, C., 1979, Architecture of the outer membrane of Escherichia coli K12. Phase transitions of the bacteriophage K3 receptor complex. Eur. J. Biochem. 101: 571–579.

    Google Scholar 

  42. Westphal, O., and Luderitz, 0., 1954. Chemische Erforschung von Lipopolysacchariden Gram-negative Bakterien. Angew. Chem. 66: 407–417.

    Google Scholar 

  43. Wollenweber, H.-W., Schlecht, S. Luderitz, O., and Rietschel, E. Th., 1983. Fatty acids in lipsopolysaccharides of Salmonella species grown at low temperature. Identification and position. Eur. J. Biochem. 130: 167–171.

    Google Scholar 

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Author information

Authors and Affiliations

  1. Institut fur Experimentelle Biologie und Medizin, Forschungsinstitut Borstel, D-2061, Borstel, Germany

    E. Th. Rietschel, L. Brade, U. Schade, U. Seydel, U. Zähringer, K. Brandenburg, I. Helander, O. Holst, S. Kondo, H. M. Kuhn, B. Lindner, E. Röhrscheidt, R. Russa & H. Brade

  2. Robert-Koch-Institut des Bundesgesundheitsamtes, D-1000, Berlin 65, Germany

    H. Labischinski & D. Naumann

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  1. E. Th. Rietschel
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  2. L. Brade
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  3. U. Schade
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  4. U. Seydel
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Editor information

Editors and Affiliations

  1. The University of South Florida, Tampa, Florida, USA

    Herman Friedman  & T. W. Klein  & 

  2. Jichi Medical School, Tochigi-Ken, Japan

    Masayasu Nakano

  3. University of Pennsylvania, Philadelphia, Pennsylvania, USA

    Alois Nowotny

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Th. Rietschel, E. et al. (1990). Bacterial Lipopolysaccharides: Relationship of Structure and Conformation to Endotoxic Activity, Serological Specificity and Biological Function. In: Friedman, H., Klein, T.W., Nakano, M., Nowotny, A. (eds) Endotoxin. Advances in Experimental Medicine and Biology, vol 256. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-5140-6_5

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  • DOI: https://doi.org/10.1007/978-1-4757-5140-6_5

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