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Structural analyses of lipid A from lipopolysaccharides of nodulating and non-nodulating Rhizobium trifolii

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Abstract

Structural studies have been performed on lipid A preparations derived from lipopolysaccharides of nodulating (nod+) Rhizobium trifolii wild type strains and non-nodulating (nod-) mutants deprived of the medium size “Nod” plasmid.

All preparations contain a lipid A backbone composed of a β1,6-linked d-glucosamine disaccharide (GlcN II-β1,6-GlcN I) which is bis-phosphorylated at positions 1 and 4′. The phosphate group at position 4′ (GlcN II) is nonstoichiometrically substituted probably by a neutral glycosyl residue. Another substituent (probably also a neutral sugar) substitutes partly position 4 (GlcN I) of the disaccharide. The hydroxyl groups at positions 3 and 3′ are likely to be esterified by fatty acyl residue. In lipid A of nod+ strains, 3-hydroxyhexa- and octadecanoic acid are linked to the amino group of GlcN I, and 3-hydroxyhexa- and tetradecanoic acid to the amino group of GlcN II. In lipid A of nod- strains, mainly 3-hydroxyhexadecanoic acid is linked to the amino group of GlcN I, and 3-hydroxytetra- and hexadecanoic acid to that of GlcN II.

The results show that rhizobial lipid A expresses many similarities to the lipid A of Enterobacteria. The structure shows, however, also peculiarities, especially regarding substituents of the lipid A backbone.

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References

  1. Ball AK, Shantharan S (1981) Localization of primary and secondary lectin recetor sites in Rhizobium japonicum. In: Gibson DH, Newton WE (eds) Current perspectives in nitrogen fixation. Australian Academy of Science, Canberra, pp 422–422

  2. Bock K, Pedersen C (1972) Reaction of sugar esters with hydrogen fluoride. Derivatives of d-glucofuranose and d-mannofuranose. Acta Chem Scand Ser B 26:2360–2366

  3. Caroff M, Szabo L (1983) Identification of 2-amino-6-O-(2-amino-2-deoxy-β-d-glucopyranosyl)-2-deoxy-d-glucose as a major constitient of the hydrophobic region of the Bordetella pertussis endotoxin. Carbohydr Res 114:95–102

  4. Dazzo FB, Brill WJ (1979) Bacterial polysaccharide which binds Rhizobium trifolii to clover root hairs. J Bacteriol 137:1362–1373

  5. Dazzo FB, Hubbell DH (1975) Cross-reactive antigens and lectin as determinants of symbiotic specificity in the Rhizobium-clover association. Appl Microbiol 30:1017–1033

  6. Hakomori S (1964) Rapid permethylation of glycolipids and polysaccharides catalyzed by methyl sulfinyl carbonion in dimethyl sulfoxide. J Biochem Tokyo 55:205–208

  7. Hase S, 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

  8. Hrabak EM, Urbano MR, Dazzo FB (1981) Growth-phase-dependent immunodeterminants of Rhizobium trifolii lipopolysaccharide which bind Trifoliin A, a white clover lectin. J Bacteriol 148:697–711

  9. Jensen M, Borowiak D, Paulsen H, Rietschel E (1979) Analysis of permethylated glucosaminyl-glucosaminitol disaccharides by combined gas-liquid chromatography/mass spectrometry. Biomed Mass Spectrom 6:559–565

  10. Kijne JD, Adhin SW, Planqué K (1977) Cell proliferation in pea root explants supplied with rhizobial LPS. In: Cell wall biochemistry related to specificity in host-plant pathogen interactions, Solheim B, Raa J (eds) Universitats-forlaget, Oslo, pp 415–416

  11. Kowalczuk E, Skorupska A, Lorkiewicz Z (1981) Transfer of nodulation ability in Rhizobium using R68.45 derived plasmids. Mol Gen Genet 183:388–391

  12. Lowry OH, Roberts NR, Leiner KY, Wu ML, Farr AL (1954) The quantitative histochemistry of brain. I. Chemical methods. J Biol Chem 207:1–17

  13. Maier RJ, Brill WJ (1978) Involvement of Rhizobium japonicum O antigen in soybean nodulation. J Bacteriol 133:1295–1299

  14. Maier RJ, Bishop PE, Brill WJ (1978) Transfer from Rhizobium japonicum to Azotobacter vinelandii of genes required for nodulation. J Bacteriol 134:1199–1201

  15. Mort AJ, Lamport DTA (1977) Anhydrous hydrogen fluoride deglycosylates glycoproteins. Anal Biochem 82:289–309

  16. Napoli C, Dazzo F, Hubell D (1975) Production of cellulose microfibrils by Rhizobium. Appl Microbiol 30:123–131

  17. Ohno K, Nishiyama H, Nagase H (1979) A mild methylation of alcohols with diazomethane catalyzed by silica gel. Tetrahed Lett 45:4405–4406

  18. Planqué K, Kijne JW (1977) Binding of pea lectins to a glycan type polysaccharide in the cell walls of Rhizobium leguminosarum. FEBS Lett 73:64–66

  19. Planqué K, Nierop JJ van, Burgers F, Wilkinson StG (1979) The lipopolysaccharide of free-living and bacteroid forms of Rhizobium leguminosarum. J Gen Microbiology 110:151–159

  20. Qureshi N, Takayama K, Ribi E (1982) Purification and structural determination of nontoxic lipid A obtained from lipopolysaccharide of Salmonella typhimurium. J Biol Chem 257:11808–11815

  21. Rietschel E Th, Hase S, King M, Redmond J, Lehman V (1977) The chemical structure of lipid A. In: Schlesinger D (ed) Microbiology 1977. Am Soc Microbiol, Washington DC, pp 262–268

  22. Rietschel E Th, Wollenweber H-W, Russa R, Brade H, Zähringer U (1984) Concepts of the chemical structure of lipid A. Rev Inf Dis 6:432–438

  23. Russa R, Lorkiewicz Z (1974) Fatty acids present in the lipopolysaccharide of Rhizobium trifolii. J Bacteriol 119:771–775

  24. Russa R, Urbanik T, Kowalczuk E, Lorkiewicz Z (1982) Correlation between the occurrence of plasmid pUCS202 and lipopolysaccharide alterations in Rhizobium. FEMS Microbiol Letters 13:161–1654

  25. Sidorczyk Z, Zähringer U, Rietschel E Th (1983) Chemical structure of the lipid A component of the lipopolysaccharide from a Proteus mirabilis Re mutant. Eur J Biochem 137:15–22

  26. Strominger JL, Park JT, Thompson RE (1959) Composition of the cell wall of Staphylococcus aureus: Its relation to the mechanism of action of penicillin. J Biol Chem 234:3263–3268

  27. Sweeley CC, Bentley R, Makita M, Wells WW (1963) Gas-liquid chromatography of trimethylsilyl derivatives of sugar and related substances. J Am Chem Soc 85:2497–2507

  28. Tharanathan RN, Weckesser J, Mayer H (1978) Structural studies on the d-arabinose-containing lipid A from Rhodospirillum tenue 2761. Eur J Biochem 84:395–394

  29. Westphal O, Jann K (1965) Bacterial lipopolysaccharides, extraction with phenol-water and further applications of the procedure. Methods Carbohydr Chem 5:83–91

  30. Wollenweber HW, Broady KW, Lüderitz O, Rietschel E Th (1982) The chemical structure of lipid A: demonstration of amidelinked 3-acyloxyacyl-residues in Salmonella minnesota Relipopolysaccharide. Eur J Biochem 124:191–198

  31. Wolpert JS, Albersheim P (1976) Symbiont interactions. I. The lectins of legumes interact with the O antigen-containing lipopolysaccharide of their symbiont Rhizobia. Biochem Biophys Res Commun 70:729–737

  32. Zajac E, Russa R, Lorkiewicz Z (1975) Lipopolysaccharide as receptor for Rhizobium phage IP. J Gen Microbiol 90:365–367

  33. Zeevenhuizen LPTM, Sholten-Koerselman I, Postumus MA (1980) Lipopolysaccharides of Rhizobium. Arch Microbiol 125:1–8

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Correspondence to Otto Lüderitz.

Additional information

This paper is dedicated to Professor Dr. Gerhart Drews on the occasion of his 60th birthday

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Russa, R., Lüderitz, O. & Rietschel, E.T. Structural analyses of lipid A from lipopolysaccharides of nodulating and non-nodulating Rhizobium trifolii . Arch. Microbiol. 141, 284–289 (1985). https://doi.org/10.1007/BF00428838

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Key words

  • Rhizobium trifolii
  • Lipopolysaccharide
  • Lipid A-structure
  • “Nod” plasmids
  • 3-Hydroxy fatty acids