Russian Journal of Bioorganic Chemistry

, Volume 31, Issue 4, pp 362–371

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

  • E. V. Vorob’eva
  • A. S. Dmitrenok
  • P. S. Dmitrenok
  • V. V. Isakov
  • I. N. Krasikova
  • T. F. Solov’eva
Article

DOI: 10.1007/s11171-005-0050-4

Cite this article as:
Vorob’eva, E.V., Dmitrenok, A.S., Dmitrenok, P.S. et al. Russ J Bioorg Chem (2005) 31: 362. doi:10.1007/s11171-005-0050-4

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 β-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 ALPSmarine proteobacteriaMarinomonas communisNMR spectroscopyFAB mass spectrometry

Abbreviations

LA

lipid A

LPS

lipopolysaccharide

GlcN

glucosamine

FA

fatty acid

EtOH

ethanol

AcOH

acetic acid

MS

mass spectrometry

FAB MS

fast atom bombardment mass spectrometry

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • E. V. Vorob’eva
    • 1
  • A. S. Dmitrenok
    • 2
  • P. S. Dmitrenok
    • 1
  • V. V. Isakov
    • 1
  • I. N. Krasikova
    • 1
  • T. F. Solov’eva
    • 1
  1. 1.Pacific Institute of Bioorganic Chemistry, Far East DivisionRussian Academy of SciencesVladivostokRussia
  2. 2.Suntory Institute for Bioorganic Research, 1-1-1Wakayamadai, Shimamoto, Mishima, OsakaJapan