Chemistry of Natural Compounds

, Volume 43, Issue 5, pp 519–524 | Cite as

Structure of lipid A from the marine gram-negative bacterium Pseudoalteromonas nigrifaciens IAM 13010T

  • A. S. Volk
  • I. N. Krasikova
  • S. D. Anastyuk
  • P. S. Dmitrenok
  • T. F. Solov’eva
Article

Abstract

The structure of lipid A from the marine γ-proteobacterium Pseudoalteromonas nigrifaciens IAM 13010T that was prepared by hydrolysis of the corresponding lipopolysaccharide by acetic acid (1%) was determined by chemical analysis, 13C NMR spectroscopy, and MALDI/TOF and LSIMS mass spectrometry. It was shown that lipid A is a β-1,6-bonded disaccharide of glucosamine that is substituted by two phosphoric acids (in the C1 and C4′ positions), two (R)-3-hydroxyalkanoic (normal and branched) acids with ester bonding (at the C3 and C3′-positions), and (R)-3-hydroxydodecanoic and (R)-3-dodecanoyloxydodecanoic acids (both with amide bonding at C2′ and C2, respectively). It was hypothesized that this type of structure is typical of lipid A from bacteria of the genus Pseudoalteromonas in general.

Key words

marine gram-negative bacteria Pseudoalteromonas nigrifaciens LPS lipid A 13C NMR spectroscopy MALDI/TOF and LSIMS mass spectrometry 

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References

  1. 1.
    S. M. Carty, K. R. Sreekumar, and C. R. H. J. Raetz, J. Biol. Chem., 274, 9677 (1999).PubMedCrossRefGoogle Scholar
  2. 2.
    I. N. Krasikova, S. I. Bakholdina, S. V. Khotimchenko, and T. F. Solov’eva, Biokhimiya (Moscow), 64, 404 (1999).Google Scholar
  3. 3.
    D. H. Bartlett and T. J. Welch, J. Bacteriol., 177, 1008 (1995).PubMedGoogle Scholar
  4. 4.
    I. N. Krasikova, N. V. Kapustina, V. V. Isakov, A. S. Dmitrenok, P. S. Dmitrenok, N. M. Gorshkova, and T. F. Solov’eva, Eur. J. Biochem., 271, 14, 2985 (2004).CrossRefGoogle Scholar
  5. 5.
    E. V. Vorob’eva, I. N. Krasikova, A. S. Dmitrenok, P. S. Dmitrenok, V. V. Isakov, O. I. Nedashkovskaya, and T. F. Solov’eva, Bioorg. Khim., 32, 5, 538 (2006).Google Scholar
  6. 6.
    I. N. Krasikova, N. V. Kapustina, V. V. Isakov, N. M. Gorshkova, and T. F. Solov’eva, Bioorg. Khim., 30, 4, 409 (2004).Google Scholar
  7. 7.
    G. Gauthier, M. Gauthier, and R. Christen, Int. J. Syst. Bacteriol., 45, 755 (1995).PubMedCrossRefGoogle Scholar
  8. 8.
    O. Westphal and O. Luderitz, Angew. Chem., 66, 407 (1954).CrossRefGoogle Scholar
  9. 9.
    O. Westphal and K. Jann, Meth. Carbohydr. Chem., 5, 83 (1965).Google Scholar
  10. 10.
    I. N. Krasikova, N. V. Kapustina, V. I. Svetashev, R. P. Gorshkova, S. V. Tomshich, E. L. Nazarenko, N. A. Komandrova, E. P. Ivanova, N. M. Gorshkova, L. A. Romanenko, V. V. Mikhailov, and T. F. Solov’eva, Biokhimiya (Moscow), 66, 8, 1286 (2001).CrossRefGoogle Scholar
  11. 11.
    J. Gmeiner, M. Simon, and O. Ludereitz, Eur. J. Biochem., 21, 3, 355 (1971).CrossRefGoogle Scholar
  12. 12.
    A. A. Ribeiro, Z. Zhou, and C. R. H. Raetz, Magn. Reson. Chem., 37, 9, 620 (1999).CrossRefGoogle Scholar
  13. 13.
    V. I. Gorbach, E. V. Ivanchina, V. V. Isakov, P. A. Luk’yanov, T. F. Solov’eva, and Yu. S. Ovodov, Bioorg. Khim., 8, 12, 1670 (1982).Google Scholar
  14. 14.
    A. P. Tulloch and M. Mazurek, Lipids, 11, 228 (1976).CrossRefGoogle Scholar
  15. 15.
    L. H. Baltzer and I. Mattsby-Baltzer, Biochemistry, 25, 12, 3570 (1986).CrossRefGoogle Scholar
  16. 16.
    H.-W. Wollenweber and E. T. Rietschel, J. Microbiol. Meth., 11, 33, 195 (1990).CrossRefGoogle Scholar
  17. 17.
  18. 18.
    U. Zahringer, R. Salvetzky, B. Lindner, and A. J. Ulmer, J. Endotox. Res., 7, 2, 133 (2001).Google Scholar
  19. 19.
    K. Leontein, B. Lindberg, and J. Lonngren, Carbohydr. Res., 62, 3, 359 (1978).CrossRefGoogle Scholar
  20. 20.
    Z. Zhou, A. A. Ribeiro, and C. R. H. Raetz, J. Biol. Chem., 275, 18, 13542 (2000).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • A. S. Volk
    • 1
  • I. N. Krasikova
    • 1
  • S. D. Anastyuk
    • 1
  • P. S. Dmitrenok
    • 1
  • T. F. Solov’eva
    • 1
  1. 1.Pacific Institute of Bioorganic Chemistry, Far-East DivisionRussian Academy of SciencesVladivostok

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