Skip to main content

Natural Variants of Lipid A

  • Chapter
Endotoxin

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

Abstract

Recent studies by several groups (46,58,61,63) have revealed that the now “classical” structure of enterobacterial lipid A, the 1,4’-bisphosphorylated β-1,6-linked glucosamine disaccharide with amide- and esterlinked 3-hydroxy fatty acids or 3-acyloxyacyl residues (25a,44), is not universally distributed amongst gram-negative bacteria. It is especially not frequently encountered in families being phylogenetically remote from Enterobacteriaceae, such as the phototrophic bacteria or the thiobacilli. (59,65).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ahamed, N. M., Mayer, H., Biebl, H. and Weckesser, J., 1982, Lipopolysaccharide with 2,3-diamino-2,3-dideoxyglucose containing lipid A in Rhodopseudomonas sulfovirids, FEMS Microbial., 14: 27–30.

    CAS  Google Scholar 

  2. Auling, G., Busse, J., Hahn, M., Hennecke, H., Kroppenstedt, R.-M., Probst, A. and Stackebrandt, E., Phylogenetic heterogeneity and chemotaxonomic properties of certain Gram-negative aerobic carboxydobacteria, Syst. Appl. Microbiol. l 10: 264–272.

    Google Scholar 

  3. Basu, S., Radziejewska-Lebrecht, J. and Mayer, H., 1986, Lipopolysaccharide of Providencia rettgeri, Chemical studies and taxonomical implication, Arch. Microbial. 144: 213–218.

    Google Scholar 

  4. Batley, M., Packer, N. H. and Redmond, J. W., 1985, Analytical studies of lipopolysaccharide and its derivatives from Salmonella minnesota 8595, Biochem. Biophys. Acta. 821: 179–194.

    Google Scholar 

  5. Bellmann, W. and Lingens, F., 1985, Structural studies on the core oligosaccharide of Phenylobacterium immobile strain K2 lipopolysaccharide. Chemical cynthesis of 3-hydroxy-5c-dodecenoic acid, Biol. Chem. Hoppe Seyler’s 366: 567–575.

    Google Scholar 

  6. Carlson, R.W., 1982, The heterogeneity of Rhizobium lipopolysaccharides, J. Bacteriol. 158: 1012–1017.

    Google Scholar 

  7. Carlson, R. W., Shetters, R., Duh, J.-L., Turnbull, E., Hanley, B., Rolfe, B. G., Djordjevvie, M. A., 1987, The isolation and partial characterization of the lipopolysaccharides from several Rhizobium trifolii mutants affected in root hair infection, Plant Physiol. 84: 421–427.

    CAS  Google Scholar 

  8. Cotter, R. J., Honovich, J., Qureshi, N. and Takayama, K., 1987, Structural determination of lipid A from gram negative bacteria using laser desorption mass spectrometry, Biomed. Environ. Mass Spectrom. 14: 591598.

    Google Scholar 

  9. Dalla Venezia, N., Minka, S., Bruneteau, M., Mayer, H. and Michel, G., 1985, Lipopolysaccharides from Yersinia pestis. Studies on lipid A of lipopolysaccharides I and II, Eur. J. Biochem., 151: 399–404.

    Google Scholar 

  10. Danner, R. L., Joiner, K. A. and Parrillo, J. E., 1987, Inhibiiton of endotoxin-induced priming of human neutrophils by lipid X and 3-azalipid X, J. Clin. Invest. 80: 605–612.

    Google Scholar 

  11. Decker, T., Lohmann-Matthes, M.-L. and Gifford, G. E., 1987, Cell associated tumor necrosis factor (TNF) as a filling mechanism of activated cytotoxic macrophages, J. Immunol. 138: 957–962.

    Google Scholar 

  12. Galanos, C., Roppel, J., Weckesser, J., Rietschel, E. Th. and Mayer, H., 1977, Biological activities of lipopolysaccharides and lipid A from Rhodospirillaceae, Infect. Immun., 16: 407–412.

    Google Scholar 

  13. Gross, M., Mayer, H., Widemann, C. and Rudolph, K., 1988, Comparative analysis of the lipopolysaccharides of a rough and a smooth strain of Pseudomonas syringae pv. phaseolicola, Arch. Microbiol., 149: 342–346.

    Google Scholar 

  14. Harvey, D. J., 1982, Picolinyl esters as derivatives for the structural determination of long chain branched and unsaturated fatty acids, Biomed. Mass Spectrom. 9: 33–38.

    Article  CAS  Google Scholar 

  15. Hase, S. and Rietschel, E. Th., 1976, Isolation and analysis of the lipid A backbone. Lipid A structure of lipopolysaccharides from various bacterial groups, Eur. J. Biochem. 63: 101–107.

    Google Scholar 

  16. Holst, 0., Borowiak, D., Weckesser, J. and Mayer, H., 1983, Structural studies on the phosphate-free lipid A of Rhodomicrobium vannielii ATCC 17100, Eur. J. Biochem. 137: 325–332.

    Google Scholar 

  17. Hurlbert, R. E., Weckesser, J., Mayer, H. and Fromme, F., 1976, Isolation and characterizatin of the lipopolysaccharide of Chromatium vinosum, Eur. J. Biochem., 68: 365–371.

    Google Scholar 

  18. Hurlbert, R. E., Weckesser, J., Tharanathan, R. N. and Mayer H., 1978, Isolation and characterization of the lipopolysaccharide of Thiocapsa roseopersicina, Eur. J. Biochem., 90: 241–246.

    Google Scholar 

  19. Kasai, N., Arata, S., Mashima, J. I., Akiyama, Y., Tanaka, C., Egawa, K. and Tanaka, S., 1987, Pseudomonas diminuta LPS with a new endotoxic lipid A structure, Biochem. Biophys. Res. Commun. 142: 972–978.

    Google Scholar 

  20. Kawahara, K., Brade, H., Rietschel, E. Th. and Zihringer, U., 1987, Studies on the chemical structure of the core-lipid A region of the lipopolysaccharide of Acinetobacter calcoaceticus NCTC 10305, Eur. J. Biochem. 163: 489–495.

    Google Scholar 

  21. Keilich, G., Roppel, J and Mayer, H., 1976, Characterization of a diaminohexose (2,3-diamino-2,3-dideoxy-D-glucose) from Rhodopseudomonas viridis lipopolysaccharides by circular dichroism, Carbohyd. Res. 5: 129–134.

    Google Scholar 

  22. Knirel, A. Y. and Kochetkov, N. K., 1987, 2,3-diamino-2,3-dideoxyuronic and 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids: new components of bacterial polysaccharides, FEMS Microbiol. Rev. 46: 381–385.

    Google Scholar 

  23. Komuro, T. and Galanos, C., 1986, Analysis of Salmonella lipopolysaccharides by sodium deoxycholate polyacrylamide gel electrophoresis, EOS-Rev. Immunol. 6: 147.

    Google Scholar 

  24. Kotelko, K., 1986, Proteus mirabilis: taxonomic positon, peculiarities of growth, components of the cell envelope, Curr. Top. Microbial. Immunol. 129: 181.

    Google Scholar 

  25. Krauss, J. H., Weckesser, J. and Mayer, H., 1988, Electrophoretic analysis of lipopolysaccharides of purple nonsulfur bacteria, J. System. Bacteriol. 38:.

    Google Scholar 

  26. Lehmann, V., Redmond, J., Egan, A. and Minner, I., 1978, The acceptor for polar head groups of the lipid A component of Salmonella lipopolysaccharides, Eur. J. Biochem. 86: 487–496.

    Google Scholar 

  27. Lúderitz, O., Galanos, C., Lehmann, V., Mayer, H., Rietschel, E. Th. and Weckesser, J., 1978, Chemical structure and biological activities of lipid A’s from various bacterial families, Naturwissenschaften 65.: 579–585.

    Google Scholar 

  28. Macher, I. and Unger, F.M., 1987, Monosaccharide derivatives related to the lipid A of enterobacteria, 4th European Carbohydrate Symposium, July 12–17, Darmstadt, FRG, B-34.

    Google Scholar 

  29. Mayer, H., 1984, Significance of lipopolysaccharide structure for questions of taxonomy and phylogenetical relatedness of gram-negative bacteria, in: “The cell membrane”, E. Harber, ed., Plenum Press, New York, London pp. 71–83.

    Google Scholar 

  30. Mayer, H. and Weckesser, J., 1984, Unusual lipid A’s: structures, taxonomical relevance and potential value for endotoxin research, in: “Handbook of endotoxin, Vol. 1, Chemistry of endotoxin, E. Th. Rietschel, ed., Elsevier Science Publishers, Amersterdam, pp. 221–247.

    Google Scholar 

  31. Mayer, H., Bock, E. and Weckesser, J., 1983, 2,3-diamino-2,3-dideoxyglucose containing lipid A in the Nitrobacter strain X14 FEMS Microbiol. Lett. 17: 93–96.

    Google Scholar 

  32. Mayer, H., Tharanathan, R. N. and Weckesser, J., 1988, Analysis of lipopolysaccharides of Gram-negative bacteria, in: “Methods in Microbiology”, G. Gottschalk, ed., Vol. 18, pp. 157–207, Academic Press, New York.

    Google Scholar 

  33. Mayer, H., Krauss, J. H., Puvanesarajah, Stacey, G. and Auling, G., 1988, Lipid A with diaminoglucose in lipopolysaccharides from slow-growing Rhizobiaceae and from Pseudomonas carboxydovorans, Arch. Microbiol. 151: 111–116.

    Google Scholar 

  34. Meissner, J., Borowiak, D., Fischer, U. and Weckesser, J., 1988, Lipopolysaccharide with lipid ADAC in the phototropic Ectohiorhodospira vacuolata, Arch. Microbiol. 149: 245–248.

    Google Scholar 

  35. Meissner, J., Fischer, U. and Weckesser, J., 1987, The lipopolysaccharide of the green sulfur bacterium Chlorobium vibrioforme f. thiosulfatophilum, Arch. Microbiol. 149: 125–129.

    Google Scholar 

  36. Meissner, J., Pfennig, N., Krauss, J., Mayer, H. and Weckesser, J., 1988, Lipopolysaccharides of the Chromatiaceae species Thiocystis violacea, Thiocapsa pfennigii, and Chromatium tepidum, J. Bacteriol. 170: 3267–3272.

    Google Scholar 

  37. Meyer zu Reckendorf, W., 1964, Die Synthesen der 2,3-Diamino-2,3-didesoxy-D-allose, der 2,3-Diamino-2,3-didesoxy-a-D-glucose und der 2,6Diamino-2,6-dideoxy-u-D-allose, Chem. Ber. 97: 1175–1285.

    Google Scholar 

  38. Moreno, E. and Mayer, H., 1988, Brucella Lipids, in: “Brucella”, CNC (London). (in press)

    Google Scholar 

  39. Moreno, E., Borowiak, D. and Mayer, H., 1987. Brucella lipopolysaccharides and polysaccharides, Ann. Inst. Pasteur Microbiol. 138: 102–105.

    Article  PubMed  CAS  Google Scholar 

  40. Ohno, K., Nishiyama, H. and Nagase, H., 1979, A mild methylation of alcohols with diazomethane catalyzed by silica gel, Tetrahedron Lett. 45: 4405–4406.

    Google Scholar 

  41. Omar, A. S., Flammann, H. T., Borowiak, D. and Weckesser, J., 1983, Lipopolysaccharides of two strains of the phototrophic bacterium Rhodopseudomonas capsulate, Arch. Microbiol. 134: 212–216.

    Google Scholar 

  42. Radziejewska-Lebrecht, Feige, U., Mayer H. and Weckesser, J., 1981, Structure of the heptose region of lipopolysaccharides from Rhodospirillum tenue, J. Bacteriol. 145: 138–144.

    CAS  Google Scholar 

  43. Raetz, C. R. H., 1987, Biosynthesis and pharmacological properties of Escherichia coli lipid A, in: “Bacterial outer membranes as model systems”, M. Inouye, ed., pp. 229–245, John Wiley and Sons, Inc.

    Google Scholar 

  44. Raetz, C. R. H., 1984, Escherichia coli mutants that allow elucidation of the precursors and biosynthesis of lipid A, in: “Handbook of Endotoxin”, E. Th. Rietschel, ed.,pp. 248–268, Elsevier Science Publishers, Amsterdam.

    Google Scholar 

  45. Rietschel, E. Th. and Luderitz, 0., 1980, Struktur von Lipopolysaccharid und Taxonomic gram-negativer Bakterien. Forum Mikrobiol. 3: 12–20.

    CAS  Google Scholar 

  46. Rietschel, E. Th., Wollenweber, H. W., Brade, H., Zahringer, U., Lindner, B., Seydel, U., Bradaczek, H., Barnickel, G., Labischinski, H. and Griesbrecht, P.. 1984, Structure and conformation of the lipid A component of lipopolysaccharides, in: “Handbook of Endotoxin”, Vol. 1. Chemistry of Endotoxin, E. Th. Rietschel, ed. pp. 187–200, Elsevier Science Publishers B. V., Amsterdam.

    Google Scholar 

  47. Rietschel, E. Th., Galanos, C.. Lüderitz, 0. and Westphal, 0., 1982, The chemistry and biology of lipopolysaccharides and their lipid A component, in: “Immunopharmacology and the regulation of leukocyte function”, Dr-R. Webb, ed., Marcel Dekker, Inc. New York, Basel, pp. 183229.

    Google Scholar 

  48. Roppel, J., Mayer, H. and Weckesser, J., 1975, Identification of a 2,3-diamino-2,3-dideoxyhexose in the lipid A component of lipopolysaccharides of Rhodopseudomonas viridis and Rhodopseudomonas palustris, Carbohydr. Res. 40: 31–40.

    Google Scholar 

  49. Russa, R., Luderitz, 0. and Rietschel, E. Th., 1985, Structural analyses of lipid A from lipopolysaccharides of nodulating and nonnodulating Rhizobiium trifolii, Archiv. Microbiol. 141: 284–289.

    CAS  Google Scholar 

  50. Salimath, P. V., Weckesser, J., Strittmatter, W. and Mayer, H., 1983, Structural studies on the nontoxic lipid A from Rhodopseudomonas sphaeroides ATCC 17023, Eur. J. Biochem. 136: 195–200.

    Google Scholar 

  51. Schinler, M. and Osborn. M. J., 1979, Interaction of divalent cations polymyxin B with lipopolysaccharide, Biochem. 18: 4425–4430.

    Article  Google Scholar 

  52. Seydel, U., Lindner, B., Zahringer, U., Rietschel, E. Th., Kusumoto, S. and Shiba, S., 1984, Laser desorption mass spectrometry of synthetic lipid A like compounds, Biomed. Mass Spectrom, 11: 132–141.

    Google Scholar 

  53. Siensky, M., 1974, Homeoviscous adaptation - a hoeostatic process that regulates the viscosity of membrane lipids in Escherichia coli, Proc. Nat. Acad. Sci. (Wash.) 71: 522–525.

    Google Scholar 

  54. Stackebrandt, E., 1986, Das hierarchische System der Eubakterien: Problem und Losungsansatze, Form Mikrobiologie 9: 255–260.

    Google Scholar 

  55. Strittmatter, W., Weckesser, J., Salimath, P. V. and Galanos, C., 1983, Nontoxic lipopolysaccharides from Rhodopseudomonas sphaeroides ATCC 17023, J. Bacteriol. 153–158.

    Google Scholar 

  56. Tegtmeyer, B., Weckesser, J., Mayer, H. and Imhoff, J. F., 1985, Chemical composition of the lipopolysaccharides of Rhodobacter sulfidophilus, Rhodopseudomonas acidophila and Rhodopseudomonas blastica, Arch. Microbiol. 143: 32–36.

    Google Scholar 

  57. Tharanathan, R. N., Salimath, P. V., Weckesser, J. and Mayer, H., 1985. The structure of lipid A from the lipopolysaccharide of Rhodopseudomonas gelatinosa 29/1, Arch. Microbiol. 141: 279–283.

    Google Scholar 

  58. Tharanathan, R. N., Weckesser, J. and Mayer, H., 1978, Structural studies on the D-arabinose-containing lipid A from Rhodospirillum tenue 2761, Eur. J. Biochem. 84: 385–394.

    Google Scholar 

  59. Wartenberg, K., Knapp, W., Ahamed, N. M., Widemann, C. and Mayer, H., 1983, Temperature-dependent changes in the sugar and fatty acid composition of lipopolysaccharides from Yersinia enterocolitica strains, Zbl. Bakt. Hyg., I., Abt. Orig. A253: 523–530.

    Google Scholar 

  60. Weckesser, J. and Mayer, H., 1987, Lipopolysaccharides of phototrophic bacteria, a contribution to phylogeny and endotoxin research, Forum Mikrobiologie, 108: 242–248.

    Google Scholar 

  61. Weckesser, J. and Mayer, H, 1987, Different lipid A types in lipopolysaccharides of phototrophic and related non-phototrophic bacteria, FEMS Microbiol. Rev.54: 143–154.

    Google Scholar 

  62. Weckesser, J., Drews, G., and Mayer, H., 1979, Lipopolysaccharides of photosynthetic prokaryotes, Ann. Rev. Microbiol. 33: 215–239.

    Google Scholar 

  63. Weisshaar, R. and Lingens, F., 1983, The lipopolysaccharide of a chloridazon-degrading bacterium, Eur. J. Biochem. 137: 155–161.

    Google Scholar 

  64. Westphal, O., Luderitz, O., Galanos, C., Mayer, H. and Rietschel, E. Th., 1985, The story of bacterial endotoxin, Adv. Immunopharmacol. 1334.

    Google Scholar 

  65. Wilkinson, S. G. and Taylor, D. P., 1978, Occurrence of 2,3-diamino-2, 3-dideoxy-D-glucose in lipid A from lipopolysaccharide of Pseudomonas diminuta, J. Gen. Microbiol. 109: 367–370.

    CAS  Google Scholar 

  66. Wilkinson, B. J., Hindahl, M. S., Galbraith, L. and Wilkinson, S. G., 1986, Lipopolysaccharide of Paracoccus denitrificans ATCC 13543, FEMS Microbiol. Lett. 37: 63–67.

    Google Scholar 

  67. Woese, C. R., 1987, Bacterial evolution, Microbiol. Rev. 51: 221–271.

    Google Scholar 

  68. Woese, C. R., Stackebrandt, E., Weisburg, W. G., Paster, B. J., Madigan, M. T., Fowler, V. J., Hahn, C. M., Blanz, P., Gupta, R., Nealson, K. H. and Fox, G. E., 1984, The phylogeny of purple bacteria: the alpha subdivision, Syst. Appl. Microbiol. 5: 315–326.

    Google Scholar 

  69. Woese, C. R., Stackebrandt, E., Weisburg, W. G., Paster, B. J., Madigan, M. T., Fowler, V. J., Hahn, C. M., Blanz, P., Gupta, R., Nealson, K. H. and Fox, G. E., 1985, The phylogeny of purple bacteria: the gamma subdivision, Syst. Appl. Microbiol. 6: 25–33.

    Google Scholar 

  70. Wollenweber, H. W., Schlecht, S., Lúderitz, 0. and Rietschel, E., 1983, Fatty acid in lipopolysaccharides of Salmonella species grown at low temperatures, Eur. J. Biochem. 130: 167–171.

    CAS  Google Scholar 

  71. Wollenweber, H. W., Seydel, U., Lindner, B., Luderitz, 0. and Rietschel, E. Th., 1984, Nature and location of amide-bound (R)3-acyloxyacyl groups in lipid A of lipopolysaccharides from various Gram-negative bacteria, Eur. J. Biochem. 145: 265–272.

    CAS  Google Scholar 

  72. Yokota, A., Rodriguez, M., Yamada, Y., Imai, K., Borowiak, D. and Mayer, H., 1987a, Lipopolysaccharides of Thiobacillus species containing lipid A with 2,3-diamino-2,3-dideoxyglucose, Arch. Microbiol. 149: 106–111.

    Google Scholar 

  73. Yokota, A., Schlecht and Mayer, H., 1987b, Lipopolysaccharides of chemolithotrophic bacteria Thiobacillus versutus and a related Thiobacillus species, FEMS Microbiol. Lett. 44: 197–201.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Springer Science+Business Media New York

About this chapter

Cite this chapter

Mayer, H., Krauss, J.H., Yokota, A., Weckesser, J. (1990). Natural Variants of Lipid A. 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_3

Download citation

  • DOI: https://doi.org/10.1007/978-1-4757-5140-6_3

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4757-5142-0

  • Online ISBN: 978-1-4757-5140-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics