NMR reinvestigation of two N-acetylneuraminic acid-containing O-specific polysaccharides (O56 and O24) of Escherichia coli

Carbohydr Res. 1995 Jul 21;272(1):73-90. doi: 10.1016/0008-6215(95)00041-q.

Abstract

Structures for the N-acetylneuraminic acid (Neu5Ac)-containing O56 and O24 polysaccharides of Escherichia coli have been reported previously. During these studies unusual chemical shifts had been observed for the NMR signals for H-3eq and C-3 of the Neu5Ac residues of both polysaccharides. In further pursuing this phenomenon, we have reinvestigated the O56 and O24 polysaccharides as well as derived oligosaccharides by one- and two-dimensional NMR spectroscopy. The results showed that structures of both polysaccharides (PSs) had to be modified and formulated as [formula: see text] 2D ROESY spectra revealed a strong NOE between H-3eq of Neu5Ac and the protons of the side-chain sugar (H-3 and H-5 of alpha-D-Gal p in the O56 PS and H-3 of alpha-D-Glc p in the O24 PS) and also between H-3ax of Neu5Ac and H-3 of beta-D-Glc p in the main chain. This indicated a close spatial association of the seven-linked alpha-Neu5Ac and the side-chain residues alpha-D-Gal p (O56 PS) and alpha-D-Glc p (O25 PS), respectively. The strong long-range spatial contacts caused the unusual chemical shifts of H-3eq and C-3 of Neu5Ac.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylgalactosamine / analysis
  • Acetylglucosamine / analysis
  • Carbohydrate Sequence
  • Escherichia coli / chemistry*
  • Escherichia coli / immunology
  • Galactose / analysis
  • Glucose / analysis
  • Lipopolysaccharides / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Monosaccharides / analysis
  • N-Acetylneuraminic Acid
  • O Antigens
  • Polysaccharides, Bacterial / chemistry*
  • Polysaccharides, Bacterial / isolation & purification
  • Sialic Acids / analysis*

Substances

  • Lipopolysaccharides
  • Monosaccharides
  • O Antigens
  • Polysaccharides, Bacterial
  • Sialic Acids
  • N-Acetylneuraminic Acid
  • Glucose
  • Acetylgalactosamine
  • Acetylglucosamine
  • Galactose