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Chemical characterization of the O-specific chain of Sphaerotilus natans ATCC 13338 lipopolysaccharide

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Abstract

The chemical structure of the O-specific chain of the Sphaerotilus natans lipopolysaccharide was established. The isolated polysaccharide moiety contained neutral sugars (rhamnose, glucose, and l-glycero-d-manno-heptose), 3-deoxy-d-manno-octulosonic acid (Kdo), phosphate and ethanolamine. Alditol acetate and methylation analyses showed that the O-specific chain contained linear pentasaccharide repeating units, composed of four units of rhamnose, substituted at 3-position, and one unit of glucose, substituted at 4-position. Oxidation by chromium trioxide showed that all sugars were α-linked. The structure proposed for the O-specific chain has been confirmed by periodate oxidation, and by 1H-and 13C-NMR spectroscopic studies for the original and the Smith-degraded PS moiety. The O-specific unit of the S. natans LPS has the following structure:

$$\begin{gathered} [ \to 4) - Glup - (1\xrightarrow{a}3) - Rhap - (1\xrightarrow{a}3) - Rhap - \hfill \\ - (1\xrightarrow{a}3) - Rhap - (1\xrightarrow{a}3) - Rhap - (1]_n \xrightarrow{a} \hfill \\ \end{gathered} $$

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Abbreviations

LPS:

lipopolysaccharide

PS:

polysaccharide

Kdo:

3-deoxy-d-manno-octulosonic acid

ld :

heptose, l-glycero-d-manno-heptose

NMR:

nuclear magnetic resonance

APT:

attached proton test

GC-MS:

gas-chromatography/mass spectrometry

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Authors and Affiliations

  1. Max-Planck-Institut für Immunbiologie, Stübeweg 51, W-7800, Freiburg, Germany

    Hussein Masoud & Hubert Mayer

  2. Central Research Institute for Chemistry of the Hungarian Academy of Sciences, Budapest, Hungary

    Andràs Neszmelyi

Authors
  1. Hussein Masoud
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  2. Andràs Neszmelyi
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  3. Hubert Mayer
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Masoud, H., Neszmelyi, A. & Mayer, H. Chemical characterization of the O-specific chain of Sphaerotilus natans ATCC 13338 lipopolysaccharide. Arch. Microbiol. 156, 176–180 (1991). https://doi.org/10.1007/BF00249111

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  • DOI: https://doi.org/10.1007/BF00249111

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