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Elucidation of Structure of Lipid A from the Marine Gram-Negative Bacterium Pseudoalteromonas haloplanktis ATCC 14393T

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Abstract

The chemical structure of lipid A, from the marine γ-proteobacterium Pseudoalteromonas haloplanktis АТСС 14393Т, a main product of lipopolysaccharide hydrolysis (1% AcOH), was determined using chemical methods and NMR spectroscopy. The lipid A was shown to be β-1,6-glucosaminobiose 1,4′-diphosphate acylated with two (R)-3-hydroxyalkanoic acid residues at C3 and C3′ and amidated with one (R)-3-hydroxydodecanoyl and one (R)-3-dodecanoyloxydodecanoyl residue at N2 and N2′, respectively.

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REFERENCES

  1. Lugtenberg, B. and van Alphen, L., Biochim. Biophys. Acta, 1983, vol. 737, pp. 51–115.

    Google Scholar 

  2. Galloway, S.W. and Raetz, C.R.H., J. Biol. Chem., 1990, vol. 265, pp. 6394–6402.

    Google Scholar 

  3. Moran, A.J., Toxicol. Toxin Revews, 1995, vol. 14, pp. 47–83.

    Google Scholar 

  4. Opal, S.I. and Yu, R.L., Jr., Drugs, 1998, vol. 55, pp. 497–508.

    Google Scholar 

  5. Wilkinson, S.G., Prog. Lipid Res., 1996, vol. 35, pp. 283–343.

    Google Scholar 

  6. Rietschel, E.Th., Brade, H., Holst, O., Brade, L., Müller-Loennies, S., Mamat, U., Zähringer, U., Beckmann, F., Seydel, U., Brandenburg, K., Ulmer, A.J., Mattern, T., Heine, H., Schletter, J., Loppnow, H., Schönbeck, U., Flad, H.-D., Hauschidt, S., Schade, F.U., Di Padova, F., Kusumoto, S., and Schuman, R.R., Curr. Topics Microbiol. Immunol.,1998, vol. 216, pp. 39–81.

    Google Scholar 

  7. Kawata, T., Bristol, J.R., and Rossignol, D.P., Br. J. Pharmacol., 1999, vol. 27, pp. 853–862.

    Google Scholar 

  8. Carty, S.M., Sreekumar, K.R., and Raetz, C.R.H., J. Biol. Chem., 1999, vol. 274, pp.9677–9685.

    Google Scholar 

  9. Krasikova, I.N., Bakholdina, S.I., Khotimchenko, S.V., and Solov'eva, T.F., Biokhimiya (Moscow), 1999, vol. 64, pp. 404–411.

    Google Scholar 

  10. Bartlett, D.H. and Welch, T.J., J. Bacteriol., 1995, vol. 177, pp. 1008–1016.

    Google Scholar 

  11. Krasikova, I.N., Kapustina, N.V., Svetashev, V.I., Gorshkova, R.P., and Tomshich, S.V., Nazarenko, E.L., Komandrova, N.A., Ivanova, E.P., Gorshkova, N.M., Romanenko, L.A., Mikhailov, V.A., and Solov'eva, T.F., Biokhimiya (Moscow), 2001, vol.66, pp. 1286–1294.

    Google Scholar 

  12. Baumann, L., Baumann, P., Mandel, M., and Allen, R.D., J. Bacteriol., 1972, vol. 3, pp.402–429.

    Google Scholar 

  13. Gauthier, G., Gauthier, M., and Christen, R.,Int. J. System. Bacteriol., 1995, vol. 45, pp. 755–764.

    Google Scholar 

  14. Baumann, P., Gauthier, M.J., and Baumann, L., Bergey's Manual of Systematic Bacteriology, Krieg, N.B. and Holt, J.G., Eds., New York: Williams & Wilkins Co, 1984, pp. 343–352.

    Google Scholar 

  15. Mullins, T.D., Britschgi, R.L., Krest, R.L., and Giovannoni, S.J., Limnol. Oceanogr., 1995, vol. 40, pp. 148–158.

    Google Scholar 

  16. Wollenweber, H.-W. and Rietschel, E.Th., J. Microbiol. Meth., 1990, vol. 11, pp. 195–211.

    Google Scholar 

  17. Gorbach, V.I., Ivanchina, E.V., Isakov, V.V., Luk'yanov, P.A., Solov'eva, T.F., and Ovodov, Yu.S., Bioorg. Khim., 1982, vol. 13, pp. 1409–1415.

    Google Scholar 

  18. Jennings, H. and Smith, I.C., Methods Enzymol., 1978, vol. 50, pp. 39–50.

    Google Scholar 

  19. Tulloch, A.P. and Mazurek, M., Lipids, 1976, vol. 11, pp. 228–234.

    Google Scholar 

  20. Baltzer, L.H. and Mattsby-Baltzer, I., Biochemistry, 1986, vol. 25, pp. 3570–3573.

    Google Scholar 

  21. Frankel, E.N., Garwood, R.F., Khambay, B.P.S., Moss, G.P., and Weedon, B.C.L.,J. Chem. Soc., Perkin Trans. I, 1984, pp. 2233–2244.

  22. Silipo, A., Lanzetta, R., Garozzo, D., Lo Cantore, P., Iacobelis, N.S., Molinaro, A., Parrilli, M., and Evidente, A., Eur. J. Biochem., 2002, vol. 269, pp. 2498–2505.

    Google Scholar 

  23. Reyes, E.D. and Carballeira, N.M., Synthesis, 1997, vol. 10, pp. 1195–1198.

    Google Scholar 

  24. Gorbach, V.I., Isakov, V.V., Kulesh, Yu.G., Luk'yanov, P.A., Solov'eva, T.F., and Ovodov, Yu.S., Bioorg. Khim., 1980, vol.6, pp. 81–86.

    Google Scholar 

  25. Corsaro, M.M., Piaz, F.D., Lanzetta, R., and Parrilli, M., J. Mass Spectrom., 2002, vol. 37, pp. 481–488.

    Google Scholar 

  26. Corsaro, M.M., Lanzetta, R., Parrilli, E., Parrilli, M., and Tutino, M.L., Eur. J. Biochem., vol. 268, pp. 5092–5097.

  27. Methods in Carbohydrate Chemistry: V. General Polysaccharides, Whistler, R.L., Ed., New York: Academic, 1965. Translated under the title Metody khimii uglevodov, Kochetkov, N.K., Ed., Moscow: Mir, 1967, pp. 325-332.

  28. Kul'shin, V.A., Yakovlev, A.P., Avaeva, S.N., and Dmitriev, B.A., Mol. Genet. Mikrobiol. Virusol., 1987, vol. 5, pp. 44–46.

    Google Scholar 

  29. Sawardeker, J.S., Sloneker, J.H., and Jeanes, A., Anal. Chem., 1965, vol.37, pp. 1602–1604.

    Google Scholar 

  30. Vaskovsky, V.E., Kostetsky, E.Y., and Vasendin, I.M., J. Chromatogr.,1975, vol. 114, pp. 129–141.

    Google Scholar 

  31. Zähringer, U., Salvetzky, R., Lindner, B., and Ulmer, A., J. Endotoxin Res., 2001, vol. 7, pp. 133–146.

    Google Scholar 

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Krasikova, I.N., Kapustina, N.V., Isakov, V.V. et al. Elucidation of Structure of Lipid A from the Marine Gram-Negative Bacterium Pseudoalteromonas haloplanktis ATCC 14393T . Russian Journal of Bioorganic Chemistry 30, 367–373 (2004). https://doi.org/10.1023/B:RUBI.0000037264.53294.da

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