Identification of 2‐Methyl‐3‐hydroxydecanoic and 2‐Methyl‐3‐hydroxytetradecanoic Acids in the ‘Lipid X’ Fraction of the <i>Bordetella pertussis</i> Endotoxin

Haeffner‐Cavaillon, Nicole; Chaby, Richard; Szabó, Ladislas

doi:10.1111/j.1432-1033.1977.tb11696.x

Cited by 49 publications

(32 citation statements)

References 12 publications

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“…Total fatty acids were liberated from lipopolysaccharide or lipid A preparations by alkaline hydrolysis (0.2 M NaOH, 100' C, 1 h) followed by acid hydrolysis (4 M HC1, lOO"C, 5 h) 1151, and finally treated with 0.5 M NaOH (IOO'C, 1 h) [33]. After acidification (pH I), free fatty acids were extracted with petroleum ether (fraction 40 -60'C)/ethyl acetate mixture (1 : 1, by vol.)…”

Section: Methods Qf Chemical Analysismentioning

confidence: 99%

Structural analysis of the lipid A component of Campylobacter jejuni CCUG 10936 (serotype O:2) lipopolysaccharide

Moran

Zähringer

Seydel

et al. 1991

European Journal of Biochemistry

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The chemical structure of Campylobucterjejuni CCUG 10936 lipid A was elucidated. The hydrophilic backbone of the lipid A was shown to consist of three (1 --f 6)-linked bisphosphorylated hexosamine disaccharides. Neglecting the phosphorylation pattern, a D-glucosamine (2-amino-2-deoxy-~-glucose) disaccharide [p-D-glUCOSaminyl-(1 --f 6)-~-glucosamine], a hybrid disaccharide of 2,3-diamino-2,3-dideoxy-~-glucose and D-glUCOSamine [2,3-diamino-2,3-dideoxy-~-~-glucopyranosyl-( 1 + 6)-~-glucosamine], and a 2,3-diamino-2,3-dideoxy-~-glucose disaccharide were present in a molar ratio of 1 : 6: 1.2. Although the backbones are bisphosphorylated, heterogeneity exists in the substitution of the polar head groups. Phosphorylethanolamine is a-glycosidically bound to the reducing sugar residue of the backbone, though C-1 is also non-stoichiometrically substituted by diphosphorylethanolamine. Position 4' of the non-reducing sugar residue carries an ester-bound phosphate group or is non-stoichiometrically substituted by diphosphorylethanolamine. By methylation analysis it was shown that position 6' is the attachment site for the polysaccharide moiety in lipopolysaccharide. These backbone species carry up to six molecules of ester-and amide-bound fatty acids. Four molecules of (R)-3-hydroxytetradecanoic acid are linked directly to the lipid A backbone (at positions 2, 3,2', and 3'). Laser desorption mass spectrometry showed that both (R)-3-hydroxytetradecanoic acids linked to the non-reducing sugar unit carry, at their 3-hydroxyl group, either two molecules of hexadecanoic acid or one molecule of tetradecanoic and one of hexadecanoic acid. It also suggested that the (R)-3-(tetradecanoyloxy)-tetradecanoic acid was attached at position 2', whereas (R)-3-(hexadecanoy1oxy)-tetradecanoic acid was attached at position 3', or at positions 2' and 3'. Therefore, the occurrence of three backbone disaccharides differing in amino sugar composition and presence of a hybrid disaccharide differentiate the lipid A of this C. ,jejuni strain from enterobacterial and other lipids A described previously.

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Section: Methods Qf Chemical Analysismentioning

confidence: 99%

Structural analysis of the lipid A component of Campylobacter jejuni CCUG 10936 (serotype O:2) lipopolysaccharide

Moran

Zähringer

Seydel

et al. 1991

European Journal of Biochemistry

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“…One of these was another ,B-hydroxy fatty acid, since GC-MS of this component gives a fragment which is characteristic of these molecules (mlz, 103) (16 weight OS (PS1 and PS2, respectively), which were separated. by gel filtration chromatography on Sephadex G-50 (24).…”

Section: Methodsmentioning

confidence: 99%

Characterization of the lipopolysaccharide from a Rhizobium phaseoli mutant that is defective in infection thread development

et al. 1987

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The lipopolysaccharide (LPS) from a Rhizobium phaseoli mutant, CE109, was isolated and compared with that of its wild-type parent, CE3. A previous report has shown that the mutant is defective in infection thread development, and sodium dodecyl sulfate-polyacrylamide gel electrophoresis shows that it has an altered LPS (K. D. Noel, K. A. VandenBosch, and B. Kulpaca, J. Bacteriol. 168:1392-1462. Mild acid hydrolysis of the CE3 LPS released a polysaccharide and an oligosaccharide, PS1 and PS2, respectively. Mild acid hydrolysis of CE109 LPS released only an oligosaccharide. Chemical and immunochemical analyses showed that CE3-PS1 is the antigenic 0 chain of this strain and that CE109 LPS does not contain any of the major sugar components of CE3-PS1. CE109 oligosaccharide was identical in composition to CE3-PS2. The lipid A's from both strains were very similar in composition, with only minor quantitative variations. Sodium dodecyl sulfatepolyacrylamide gel electrophoresis of CE3 and CE109 LPSs showed that CE3 LPS separated into two bands, LPS I and LPS H, while CE109 had two bands which migrated to positions similar to that of LPS II. Immunoblotting with anti-CE3 antiserum showed that LPS I contains the antigenic 0 chain of CE3, PS1. Anti-CE109 antiserum interacted strongly with both CE109 LPS bands and CE3 LPS II and interacted weakly with CE3 LPS I. Mild-acid hydrolysis of CE3 LPS I, extracted from the polyacrylamide gel, showed that it contained both PS1 and PS2. The results in this report showed that CE109 LPS consists of only the lipid A core and is missing the antigenic 0 chain.

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“…Endotoxin from virulent B. pertussis is composed of two major types of LPS: LPS-I, which contains lipid X; and LPS-II, which contains lipid A and two different polysaccharides (PS1 and PS2). Lipid X is different in that it contains 2-methyl-3-hydroxydecanoic and -tetradecanoic acids while lipid A does not (59). PS1 is bound to lipid A via a molecule of nonphosphorylated 3-deoxy-2-octulosonic acid, while PS2 is bound to lipid A via a molecule of phosphorylated 3-deoxy-2-octulosonic acid.…”

Section: Tctmentioning

confidence: 99%

Pertussis: the disease and new diagnostic methods

Friedman

1988

Clin Microbiol Rev

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Bordetella pertussis, the causative agent of whooping cough, produces an acute and chronic respiratory infection in infants and young children. B. pertussis is still a major health problem of young children throughout the world even though effective immunization against whooping cough is available. While predominantly a childhood disease, it has been reported also to be a cause of persistent cough in adults. This review discusses the numerous bacterial virulence factors that may play roles in the pathogenesis of pertussis and in immunity to infection. The present problems with pertussis diagnosis, recent advances, and future prospects for new and improved rapid diagnostics tests also are explored.

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Identification of 2‐Methyl‐3‐hydroxydecanoic and 2‐Methyl‐3‐hydroxytetradecanoic Acids in the ‘Lipid X’ Fraction of the Bordetella pertussis Endotoxin

Cited by 49 publications

References 12 publications

Structural analysis of the lipid A component of Campylobacter jejuni CCUG 10936 (serotype O:2) lipopolysaccharide

Structural analysis of the lipid A component of Campylobacter jejuni CCUG 10936 (serotype O:2) lipopolysaccharide

Characterization of the lipopolysaccharide from a Rhizobium phaseoli mutant that is defective in infection thread development

Pertussis: the disease and new diagnostic methods

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