Elsevier

Carbohydrate Research

Volume 304, Issue 1, 28 October 1997, Pages 77-79
Carbohydrate Research

Preliminary communication
Chemical characterization of a new 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acid released by mild acid hydrolysis of the Legionella pneumophila serogroup 1 lipopolysaccharide

https://doi.org/10.1016/S0008-6215(97)00211-5Get rights and content

Abstract

A derivative of a new 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acid was released from the lipopolysaccharide of Legionella pneumophila serogroup 1 (strain Philadelphia 1) by mild acid hydrolysis, and identified, using NMR spectroscopy and GLC-MS, as 5,7-diacetamido-8-O-acetyl-3,5,7,9-tetradeoxy-l-glycero-d-talo-nonulosonic acid or its enantiomer.

A derivative of a new 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acid was released from the lipopolysaccharide of Legionella pneumophila serogroup 1 (strain Philadelphia 1) by mild acid hydrolysis and identified as 5,7-diacetamido-8-O-acetyl-3,5,7,9-tetradeoxy-l-glycero-d-talo-nonulosonic acid or its enantiomer.

References (12)

  • Y.A. Knirel et al.

    Carbohydr. Res.

    (1996)
  • I. Ciucanu et al.

    Carbohydr. Res.

    (1984)
  • P. Edebrink et al.

    Carbohydr. Res.

    (1996)
  • Y.A. Knirel et al.

    Carbohydr. Res.

    (1985)
  • H. Friedman et al.

    Adv. Exp. Med. Biol.

    (1988)
  • Y.A. Knirel et al.

    Eur. J. Biochem.

    (1994)
There are more references available in the full text version of this article.

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