Structure of the O-specific polysaccharide of Hafnia alvei PCM 1222 containing 2-aminoethyl phosphate

Carbohydr Res. 1996 Dec 13:295:117-26. doi: 10.1016/s0008-6215(96)90130-5.

Abstract

The O-specific polysaccharide of H. alvei strain PCM 1222 has a branched hexasaccharide repeating unit containing D-galactose, L-rhamnose, D-ribose, D-galacturonic acid, and 2-acetamido-2-deoxy-D-glucose in the ratios 1:2:1:1:1, as well as 2-aminoethyl phosphate (EtNP) and O-acetyl groups in nonstoichiometric amounts. The polysaccharide was modified by carboxyl reduction, O-deacetylation, and dephosphorylation with 48% hydrofluoric acid, the last reaction being accompanied by removal of the lateral residue of beta-galactofuranose. The modified polysaccharides were studied by methylation analysis and 1H and 13C NMR spectroscopy, including 2D correlation spectroscopy (COSY), H-detected 1H,13C and 1H,31P heteronuclear multiple-quantum coherence (HMQC), 1D NOE, 2D rotating-frame NOE spectroscopy (ROESY), and 2D combined total correlation spectroscopy (TOCSY) and ROESY (TORO). The following structure of the O-deacetylated polysaccharide was established: [formula: see text] In different batches of the polysaccharide, the content of EtNP varied from 0.35 to 0.55 and that of the O-acetyl groups from 0.05 to 0.4 per repeating unit. It was tentatively suggested that the O-acetyl group is located at position 4 of a rhamnosyl residue.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoethylphosphonic Acid / chemistry*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Enterobacteriaceae / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • O Antigens / chemistry*
  • Oligosaccharides / analysis
  • Oligosaccharides / chemistry
  • Polysaccharides, Bacterial / chemistry*
  • Repetitive Sequences, Nucleic Acid
  • Sequence Analysis

Substances

  • O Antigens
  • Oligosaccharides
  • Polysaccharides, Bacterial
  • Aminoethylphosphonic Acid