Russian Journal of Bioorganic Chemistry, Vol. 31, No. 4, 2005, š . 362

The Structure of Uncommon Lipid A from the Marine Bacterium Marinomonas communis ATCC 27118 T 1

E. V. Vorob’eva*, 2 A. S. Dmitrenok**, P. S. Dmitrenok*, V. V. Isakov*, I. N. Krasikova *, and T. F. Solov’eva*

* Pacific Institute of Bioorganic Chemistry, Far East Division, Russian Academy of Sciences, pr. 100-letiya Vladivostoka 159, Vladivostok, 690022 Russia, ** Suntory Institute for Bioorganic Research, 1-1-1, Wakayamadai, Shimamoto, Mishima, Osaka, 618-8503 Japan

Abstract: Lipid A was obtained in a high yield (27%) by the hydrolysis of lipopolysaccharide from the marine gamma proteobacterium Marinomonas communis ATCC 27118T with 1% AcOH. Using chemical analysis and 1D and 2D NMR spectroscopic and fast atom bombardment mass spectrometric methods, it was shown to be -1',6-linked D-glucosaminobiose 1-phosphate acylated with (R)-3-dodecanoyl- or (R)-3-decanoyloxydecanoic acid, (R)-3-{(R)-3-hydroxydecanoyloxy)]decanoic acid and (R)-3-hydroxydecanoic acid at the C2, C2' and C3 positions, respectively. Uncommon structural peculiarities (a low acylation and phosphorylation degree) of the M. communis lipid A in comparison with those of terrestrial bacteria may be of pharmacological interest. The potential physiological meaning of this lipid A and compounds of similar structure are discussed.

Key words: lipid A, LPS, marine proteobacteria, Marinomonas communis, NMR spectroscopy, FAB mass spectrometry