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Archives of Microbiology

, Volume 123, Issue 3, pp 295–299 | Cite as

N-Acetyltalosaminuronic acid a constituent of the pseudomurein of the genus Methanobacterium

  • Helmut König
  • Otto Kandler
Article

Abstract

By various chemical procedures including ninhydrin-degradation it is shown that the as of yet unknown compound found in partial acid hydrolysates of isolated cell walls of Methanobacterium thermoautotrophicum and other species of this genus is 2-amino-2-deoxy-taluronic acid (N-Acetyltalosaminuronic acid) together with N-acetylglucosamine. It forms the glycan moiety of pseudomurein.

Key words

Methanobacterium Cell wall Pseudomurein Talosaminuronic acid 2-Amino-2-deoxy-taluronic acid 

Abbreviations

PEP

phosphoenolpyruvate

UDP-GlcNAc

uridindiphospho-N-acetylglucosamine

MurNAc

N-acetylmuramic acid

NAcTalNUA

N-acetyltalosaminuronic acid

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References

  1. Albersheim, P., Nevins, D. J., English, P. D., Karr, A.: A method for the analysis of sugars in plant cell-wall polysaccharides by gas liquid chromatography. Carbohydr. Res. 5, 340–345 (1967)CrossRefGoogle Scholar
  2. Clotten, R., Clotten, A.: Hochspannungselektrophorese. Stuttgart: Thieme 1962Google Scholar
  3. Drews, G., Weckesser, J., Mayer, H.: Cell Envelopes. In: The Photosynthetic Bacteria (R. K. Clayton and W. R. Sistrom, eds.), pp. 61–77. Plenum Publishing Corporation 1978Google Scholar
  4. Hanessian, S., Haskel, T. H.: Structural studies on staphylococcal polysaccharide antigen. J. Biol. Chem. 239, 2758–2764 (1964)PubMedGoogle Scholar
  5. Hase, S., Matsushima, Y.: Structural studies on a glucose containing polysaccharide obtained from Micrococcus lysodeikticus cell wall I. J. Biochem. 68, 723–730 (1970)PubMedGoogle Scholar
  6. Hase, S., Matsushima, Y.: Structural studies on a glucose-containing polysaccharide obtained from cell walls of Micrococcus lysodeikticus III. Determination of the structure. J. Biochem. 72, 1117–1128 (1972)PubMedGoogle Scholar
  7. Heyns, K., Kiessling, G., Lindenberg, W., Paulsen, H., Webster, M.: D-Galactosaminuronsäure (2-Amino-2-desoxy-D-galacturonsäure) als Baustein des Vi-Antigens. Chem. Ber. 92, 2435–2438 (1959)Google Scholar
  8. Heyns, K., Kiessling, G.: Strukturaufklärung des Vi-Antigens aus Citrobacter freundii (E. coli) 5396/38. Carbohydr. Res. 3, 340–353 (1967)CrossRefGoogle Scholar
  9. Horton, D.: Monosaccharide amino sugars. In: The amino sugars Vol. IA (R. W. Jeanloz, ed.), pp. 1–211. New York, London: Academic Press 1969Google Scholar
  10. Jeanes, A., Burton, K. A., Cadmus, M. C., Knutson, C. A., Rowin, G. L., Sandford, P. A.: Extracellular black yeast polysaccharide composed of N-acetyl-glucosamine and N-acetylglucosaminuronic acid. Nature (New Biol.) 233, 259–260 (1971)Google Scholar
  11. Johnson, A. R.: Improved method for hexosamine determination. Anal. Biochem. 44, 628–635 (1971)PubMedGoogle Scholar
  12. Kandler, O.: Zellwandstrukturen bei Methan-Bakterien. Naturwissenschaften 66, 95–105 (1979)Google Scholar
  13. Kandler, O., König, H.: Chemical composition of the peptidoglycan-free cell walls of methanogenic bacteria. Arch. Microbiol. 118, 141–152 (1978)PubMedGoogle Scholar
  14. König, H., Kandler, O.: The amino acid sequence of the peptide moiety of the pseudomurein from Methanobacterium thermoautotrophicum. Arch. Microbiol. 121, 271–275 (1979)PubMedGoogle Scholar
  15. Kontrohr, T.: The identification of 2-amino-2-deoxy-L-altruronic acid as a constituent of Shigella sonnei phase I lipopolysaccharide. Carbohydr. Res. 58, 498–500 (1977)CrossRefPubMedGoogle Scholar
  16. Männel, D., Mayer, H.: Isolation and chemical characterization of the enterobacterial common antigen. Eur. J. Biochem. 86, 361–370 (1978)PubMedGoogle Scholar
  17. Nasir-ud-Din Jeanloz, R. W.: The chemical structure of a fragment of Micrococcus lysodeikticus cell wall. Carbohydr. Res. 47, 245–260 (1976)CrossRefPubMedGoogle Scholar
  18. Patridge, S. M.: Aniline hydrogen phthalate as a spraying reagent for chromatography of sugars. Nature 164, 443 (1949)Google Scholar
  19. Perkins, H. R.: A polymer containing glucose and aminohexuronic acid isolated from the cell walls of Micrococcus lysodeikticus. Biochem. J. 86, 475–483 (1963)PubMedGoogle Scholar
  20. Reistad, R.: 2-Amino-2-deoxyguluronic acid: a constituent of the cell wall of Halococcus sp., strain 24. Carbohydr. Res. 36, 420–423 (1974)CrossRefPubMedGoogle Scholar
  21. Reistad, R.: Amino sugar and amino acid constituents of the cell walls of the extremely halophilic cocci. Arch. Microbiol. 102, 71–73 (1975)PubMedGoogle Scholar
  22. Rohr, T. E., Levy, G. N., Stark, N. J., Anderson, J. S.: Initial reactions in biosynthesis of teichuronic acid of Micrococcus lysodeikticus cell walls. J. Biol. Chem. 252, 3460–3465 (1977)PubMedGoogle Scholar
  23. Smith, E. J.: Purification and properties of an acidic polysaccharide isolated from Achromobacter georgiopolianum. J. Biol. Chem. 243, 5139–5144 (1968)PubMedGoogle Scholar
  24. Stark, N. J., Levy, G. N., Rohr T. E., Anderson, J. S.: Reactions of second stage of biosynthesis of teichuronic acid of Micrococcus lysodeikticus cell walls. J. Biol. Chem. 252, 3466–3472 (1977)PubMedGoogle Scholar
  25. Steber, J.: Untersuchungen zur chemischen Zusammensetzung und Struktur der Zellwand von Halococcus morrhuae. Diss., Univ. München 1976Google Scholar
  26. Stoffyn, P. J.: Ninhydrin degradation of hexosamines and perodic acid oxidation of hexoses. J. Org. Chem. 24, 1360–1362 (1959)Google Scholar
  27. Tipper, D. J.: Alkali-catalyzed elimination of D-lactic acid from muramic acid and its derivatives and the determination of muramic acid. Biochemistry 7, 1441–1449 (1968)Google Scholar
  28. Torii, M., Sakakibara, K., Kuroda, K.: Occurrence of 2-amino-2-deoxyhexuronic acid as constituents of Vibrio parahaemolyticus K15 antigen. Eur. J. Biochem. 37, 401–405 (1973)PubMedGoogle Scholar
  29. Trevelyan, W. E., Procter, D. D., Harrison, J. S.: Detection of sugars on paper chromatograms. Nature 166, 444–445 (1950)Google Scholar
  30. Wheat, R. W.: Analysis of hexosamines in bacterial polysaccharides by chromatographic procedures. In: Methods in Enzymology, Vol. VIII (E. F. Neufeld, V. Ginsburg, eds.), pp. 60–78. New York, London: Academic Press 1966Google Scholar
  31. Wilkinson, S. G.: Amino components of the lipopolysaccharide from Pseudomonas aeruginosa. N. C. T. C. 8505. Biochem. J. 161, 103–109 (1977)PubMedGoogle Scholar
  32. Williamson, A. R., Zamenhof, S.: The type-specific substance of Hemophilus influenzae, type d: the natural occurence of glucosamine uronic acid. J. Biol. Chem. 238, 2255–2258 (1963)PubMedGoogle Scholar
  33. Woese, C. R., Magrum, L. J., Fox, G. E.: Archaebacteria. J. Mol. Evol. 11, 245 (1978)PubMedGoogle Scholar
  34. Wu, T. C. M., Park, J. T.: Chemical characterization of a new surface antigenic polysaccharide from a mutant of Staphylococcus aureus. J. Biol. Chem. 108, 874–884 (1971)Google Scholar

Copyright information

© Springer-Verlag 1979

Authors and Affiliations

  • Helmut König
    • 1
  • Otto Kandler
    • 1
  1. 1.Botanisches Institut der Universität MünchenMünchen 19Bundesrepublik Deutschland

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