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Structure of the O-specific polysaccharide ofProteus vulgarisO15 containing a novel regioisomer ofN-acetylmuramic acid, 2-acetamido-4-O-[(R)-1-carboxyethyl]-2-deoxy-d-glucose

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
337
Issue
24
Identifiers
DOI: 10.1016/s0008-6215(02)00226-4
Keywords
  • Proteus Vulgaris
  • Lipopolysaccharide
  • O-Antigen
  • Bacterial Polysaccharide Structure
  • 2-Acetamido-4-O-[(R)-1-Carboxyethyl]-2-Deoxy-D-Glucose
  • Triflic Acid Solvolysis
  • 6-Deoxy-L-Talose

Abstract

Abstract An acidic O-specific polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Proteus vulgaris O15 and studied by sugar and methylation analyses along with 1H and 13C NMR spectroscopy, including 2D COSY, TOCSY, ROESY, and H-detected 1H, 13C HMQC experiments. The polysaccharide was found to contain an ether of GlcNAc with lactic acid, and the following structure of the repeating unit was established: →3)- α- d - Glcp NAc4(R- Lac)6 Ac-(1 →2)- β- d - Glcp A-(1 →3)- α- l -6 dTalp2 Ac-(1 →3)- β- d - Glcp NAc-(1 → where l-6dTal and d-GlcNAc4( R-Lac) are 6-deoxy- l-talose and 2-acetamido-4- O-[( R)-1-carboxyethyl]-2-deoxy- d-glucose, respectively. The latter sugar, which to our knowledge has not been hitherto found in nature, was isolated from the polysaccharide by solvolysis with anhydrous triflic acid and identified by comparison with the authentic synthetic compound. Serological studies with the Smith-degraded polysaccharide showed an importance of 2-substituted GlcA for manifesting of the immunospecificity of P. vulgaris O15.

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