Structures of cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106

Biochemistry (Mosc). 2004 Dec;69(12):1353-9. doi: 10.1007/s10541-005-0080-9.

Abstract

Structures of two cell wall teichoic acids of Brevibacterium iodinum VKM Ac-2106 were studied. The structure of mannitol teichoic acid described earlier was mainly confirmed. This polymer is 1,6-poly(mannitol phosphate) bearing beta-D-glucopyranosyl residues at the C-2 of mannitol and pyruvic acid residues at the C-4 and C-5. The absolute configurations of D-mannitol and S-pyruvic acid were found. The following distinctions from the earlier described structure were found: unsubstituted 1,6-poly(mannitol phosphate) residues and residues substituted only by beta-D-glucopyranosyl at the C-2 of mannitol but unsubstituted by pyruvic acid are present in the chain. The structure of glycerol teichoic acid present in the cell wall as a minor component (approximately 7%) is also described. This acid is identified as 1,3-poly(glycerol phosphate) substituted at the C-2 of glycerol by 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residues bearing R-pyruvic acid residues at the C-4 and C-6 of galactose. This polymer is for the first time described in the cell wall of Gram-positive bacteria.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Brevibacterium / chemistry*
  • Cell Wall / chemistry*
  • Glucose / analysis
  • Glucose / chemistry
  • Glycerol / analysis
  • Glycerol / chemistry
  • Mannitol / analysis
  • Mannitol / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Teichoic Acids / chemistry*

Substances

  • Teichoic Acids
  • Mannitol
  • Glucose
  • Glycerol