The structure of lipid A of the lipopolysaccharide from Burkholderia caryophylli with a 4-amino-4-deoxy-L-arabinopyranose 1-phosphate residue exclusively in glycosidic linkage

Chemistry. 2003 Apr 4;9(7):1542-8. doi: 10.1002/chem.200390177.

Abstract

From the lipopolysaccharides (LPSs) of the plant-pathogenic bacterium Burkholderia caryophylli, the complete structure of lipid A has been characterized. For the first time, a 4-amino-4-deoxy-L-arabinopyranose 1-phosphate residue was proven to be exclusively linked to the reducing end of lipid A from a wild-type LPS. The LPSs of B. caryophylli were degraded by mild acetate buffer hydrolysis at pH 4.4. The obtained lipid A was analyzed as such, and also after de-O-acylation or dephosphorylation. The structure of lipid A was identified mainly by means of matrix-assisted laser desorption/ionisation mass spectrometry, and by various 1D and 2D (1)H and (13)C NMR spectroscopic measurements.

MeSH terms

  • Acylation
  • Arabinose / chemistry*
  • Burkholderia / chemistry*
  • Burkholderia / metabolism
  • Carbohydrate Conformation
  • Glycosides / chemistry*
  • Lipid A / chemistry*
  • Lipid A / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Organophosphates / chemistry*
  • Phosphorylation
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Glycosides
  • Lipid A
  • Organophosphates
  • Arabinose