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).
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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.
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.
Basu, S., Radziejewska-Lebrecht, J. and Mayer, H., 1986, Lipopolysaccharide of Providencia rettgeri, Chemical studies and taxonomical implication, Arch. Microbial. 144: 213–218.
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.
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.
Carlson, R.W., 1982, The heterogeneity of Rhizobium lipopolysaccharides, J. Bacteriol. 158: 1012–1017.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Komuro, T. and Galanos, C., 1986, Analysis of Salmonella lipopolysaccharides by sodium deoxycholate polyacrylamide gel electrophoresis, EOS-Rev. Immunol. 6: 147.
Kotelko, K., 1986, Proteus mirabilis: taxonomic positon, peculiarities of growth, components of the cell envelope, Curr. Top. Microbial. Immunol. 129: 181.
Krauss, J. H., Weckesser, J. and Mayer, H., 1988, Electrophoretic analysis of lipopolysaccharides of purple nonsulfur bacteria, J. System. Bacteriol. 38:.
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.
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.
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.
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.
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.
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.
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.
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.
Meissner, J., Borowiak, D., Fischer, U. and Weckesser, J., 1988, Lipopolysaccharide with lipid ADAC in the phototropic Ectohiorhodospira vacuolata, Arch. Microbiol. 149: 245–248.
Meissner, J., Fischer, U. and Weckesser, J., 1987, The lipopolysaccharide of the green sulfur bacterium Chlorobium vibrioforme f. thiosulfatophilum, Arch. Microbiol. 149: 125–129.
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.
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.
Moreno, E. and Mayer, H., 1988, Brucella Lipids, in: “Brucella”, CNC (London). (in press)
Moreno, E., Borowiak, D. and Mayer, H., 1987. Brucella lipopolysaccharides and polysaccharides, Ann. Inst. Pasteur Microbiol. 138: 102–105.
Ohno, K., Nishiyama, H. and Nagase, H., 1979, A mild methylation of alcohols with diazomethane catalyzed by silica gel, Tetrahedron Lett. 45: 4405–4406.
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.
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.
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.
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.
Rietschel, E. Th. and Luderitz, 0., 1980, Struktur von Lipopolysaccharid und Taxonomic gram-negativer Bakterien. Forum Mikrobiol. 3: 12–20.
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.
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.
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.
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.
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.
Schinler, M. and Osborn. M. J., 1979, Interaction of divalent cations polymyxin B with lipopolysaccharide, Biochem. 18: 4425–4430.
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.
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.
Stackebrandt, E., 1986, Das hierarchische System der Eubakterien: Problem und Losungsansatze, Form Mikrobiologie 9: 255–260.
Strittmatter, W., Weckesser, J., Salimath, P. V. and Galanos, C., 1983, Nontoxic lipopolysaccharides from Rhodopseudomonas sphaeroides ATCC 17023, J. Bacteriol. 153–158.
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.
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.
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.
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.
Weckesser, J. and Mayer, H., 1987, Lipopolysaccharides of phototrophic bacteria, a contribution to phylogeny and endotoxin research, Forum Mikrobiologie, 108: 242–248.
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.
Weckesser, J., Drews, G., and Mayer, H., 1979, Lipopolysaccharides of photosynthetic prokaryotes, Ann. Rev. Microbiol. 33: 215–239.
Weisshaar, R. and Lingens, F., 1983, The lipopolysaccharide of a chloridazon-degrading bacterium, Eur. J. Biochem. 137: 155–161.
Westphal, O., Luderitz, O., Galanos, C., Mayer, H. and Rietschel, E. Th., 1985, The story of bacterial endotoxin, Adv. Immunopharmacol. 1334.
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.
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.
Woese, C. R., 1987, Bacterial evolution, Microbiol. Rev. 51: 221–271.
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.
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.
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.
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.
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.
Yokota, A., Schlecht and Mayer, H., 1987b, Lipopolysaccharides of chemolithotrophic bacteria Thiobacillus versutus and a related Thiobacillus species, FEMS Microbiol. Lett. 44: 197–201.
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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
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