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Journal of Lipid Research, Vol. 50, 854-859, May 2009
Copyright © 2009 by American Society for Biochemistry and Molecular Biology

Structural characterization of Bordetella parapertussis lipid A

Asmaa El Hamidi^*, Alexey Novikov^*, Doris Karibian^*, Malcolm B. Perry and Martine Caroff^1,*

^* Equipe "Endotoxines," UMR 8619 du Centre National de la Recherche Scientifique, Université de Paris-Sud, Orsay, France
Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada

Published, JLR Papers in Press, November 17, 2008.

¹ To whom correspondence should be addressed. e-mail: Martine.Caroff{at}u-psud.fr

Bordetella parapertussis like B. pertussis, is a causal agent of whooping cough but is not a strictly human pathogen. Because its endotoxin, a major structural component of the Gram-negative outer membrane, is an important virulence factor, we have analyzed the structure of its toxic lipid domain, in one rough and two smooth bacterial strains. Chemical analyses and mass spectra obtained before and after recently developed mild-alkali treatments revealed that the lipids A have the common bisphosphorylated β-(16)-linked D-glucosamine disaccharide with hydroxytetradecanoic acid in amide linkages. All three strains have two major molecular species: a tetraacyl and a pentaacyl species. The rough strain is richer in a minor hexaacyl species. Acylation at the C-2, C-3, and C-3' positions was different from that of the B. pertussis lipid A. The C-2 position carries a secondary hexadecanoic acid, the C-3 position is free, and the C-3' position is substituted with hydroxydecanoic acid (not at C-3 as in B. pertussis), and the rough strain hexaacyl species carries a second secondary hexadecanoic acid. Like the lipid A of B. pertussis, the hydroxytetradecanoic acid at the C-2' position was substituted by tetradecanoic acid.

Supplementary key words B. parapertussis • endotoxin • lipopolysaccharide • structure

Abbreviations: C₁₂, dodecanoic acid; C₁₄, tetradecanoic acid; C₁₆, hexadecanoic acid; C₁₀-OH, hydroxydecanoic acid; C₁₂-OH, hydroxydodecanoic acid; C₁₄-OH, hydroxytetradecanoic acid; GlcN, D-glucosamine; LPS, lipopolysaccharide

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