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Glycobiology Advance Access published online on December 15, 2004
Glycobiology, doi:10.1093/glycob/cwi029
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© Oxford University Press 2004; all rights reserved.
Received November 15, 2004
Revised December 11, 2004
Accepted December 13, 2004

Research Article

Complete structural characterization of the lipid A fraction of a clinical strain of B. cepacia genomovar I lipopolysaccharide

Alba Silipo 1, Antonio Molinaro 1*, Paola Cescutti 2, Emiliano Bedini 1, Roberto Rizzo 2, Michelangelo Parrilli 1, and Rosa Lanzetta 1

1 Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy
2 Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole Università degli Studi di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy

* To whom correspondence should be addressed.
Antonio Molinaro, E-mail: molinaro{at}unina.it


  Abstract

Burkholderia cepacia, a Gram negative bacterium ubiquitous in the environment, is a plant pathogen causing soft rot of onions. This microorganism has recently emerged as a life-threatening multiresistant pathogen in cystic fibrosis patients. An important virulence factor of B. cepacia is the lipopolysaccharide fraction. Clinical isolates and environmental strains possess LPS of high inflammatory nature which induces a high level production of cytokines. For the first time, the complete structure of the lipid A components isolated from the lipopolysaccharide fraction of a clinical strain of Burkholderia cepacia is herein described. The structural studies carried out by selective chemical degradations, mass spectrometry and NMR spectroscopy revealed multiple species differing in the acylation and in the phosphorylation patterns. The highest mass species was identified as a penta-acylated tetrasaccharide backbone containing two phosphoryl-arabinosamine residues in addition to the archetypal glucosamine disaccharide [Arap4N-L-{beta}-1-P>4-{beta}-D-GlcpN-(1>6)-{alpha}-D-GlcpN-1>P-1-{beta}-L-Arap4N]. Lipid A fatty acids substitution was also described, with two 3-hydroxytetradecanoic acids 14:0 (3-OH) in ester linkage, and two 3-hydroxyhexadecanoic acids 16:0 (3-OH) in amide-linkage, one of which was substituted by a secondary a 14:0 residue at its C-3. Other lipid A species present in the mixture and exhibiting lower molecular weight lacked one or both {beta}-L-Arap4N residues.

Keywords: Burkholderia cepacia/lipid A/lipopolysaccharide/Mass spectrometry/NMR spectroscopy..
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