Chemical Structure of Lipid A From Porphyromonas (Bacteroides) Gingivalis Lipopolysaccharide

FEBS Lett. 1993 Oct 11;332(1-2):197-201. doi: 10.1016/0014-5793(93)80512-s.

Abstract

The novel chemical structure of Porphyromonas (Bacteroides) gingivalis strain 381 lipid A was determined to be a glucosamine beta-(1-6) disaccharide 1-monophosphate acylated by 3-hydroxy-15-methylhexadecanoic acid and 3-hexadecanoyloxy-15-methylhexadecanoic acid at the 2- and 2'-positions, respectively. The absence of ester-linked phosphate at the 4'-position and fatty acids at the 3- and 3'-positions, and the presence of fatty acids possessing 16-17 carbon atoms are unique features, differentiating the lipid A from enterobacterial and other lipid As. These structural features may be related to its low endotoxic activity. Furthermore, P. gingivalis lipid A as well as its LPS stimulated the splenocytes from C3H/HeN and C3H/HeJ mice.

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Fatty Acids / analysis
  • Lipid A / chemistry*
  • Lipopolysaccharides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Mice, Inbred C3H
  • Molecular Sequence Data
  • Molecular Structure
  • Porphyromonas gingivalis / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Fatty Acids
  • Lipid A
  • Lipopolysaccharides