Mēthylation de dērivēs n-acylēs du 2-amino-2-dēsoxy-D-glucose en prēsence de sels d'argent: observations sur le comportement du groupement ambident acetamido (ou benzamido)

Kraska, Ursula; Pougny, Jean-René; Sina, Pierre

doi:10.1016/s0008-6215(00)83849-5

Cited by 21 publications

(2 citation statements)

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“…Ester-linked fatty acids were likewise characterized after hydrazinolysis (26) of the lipid A with an internal standard of octadecanoic acid for quantitation. Secondary acylation of amide-linked fatty acids was identified by the method of Kraska et al (23) as modified by Wollenweber and Rietschel (37) and by gas chromatographymass spectrometry analysis of the diazomethane-methylated products. Synthetic acyloxyacyl fatty acids, provided by D. Charon, were used as reference.…”

Section: Methodsmentioning

confidence: 99%

Structural characterization of the lipids A of three Bordetella bronchiseptica strains: variability of fatty acid substitution

et al. 1997

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The structures of lipids A isolated from the lipopolysaccharides (LPSs; endotoxins) of three different pathogenic Bordetella bronchiseptica strains were investigated by chemical composition and methylation analysis, gas chromatography-mass spectrometry, nuclear magnetic resonance, and plasma desorption mass spectrometry (PDMS). The analyses revealed that the LPSs contain the classical lipid A bisphosphorylated ␤-(136)-linked D-glucosamine disaccharide with hydroxytetradecanoic acid in amide linkages. Their structures differ from that of the lipid A of Bordetella pertussis endotoxin by the replacement of hydroxydecanoic acid on the C-3 position with hydroxydodecanoic acid or dodecanoic acid and the presence of variable amounts of hexadecanoic acid. The dodecanoic acid is the first nonhydroxylated fatty acid to be found directly linked to a lipid A glucosamine. The lipids A were heterogeneous and composed of one to three major and several minor molecular species. The fatty acids in ester linkage were localized by PDMS of chemically modified lipids A. B. pertussis lipids A are usually hypoacylated with respect to those of enterobacterial lipids A. However, one of the three B. bronchiseptica strains had a major hexaacylated molecular species. C-4 and C-6 hydroxyl groups of the backbone disaccharide were unsubstituted, the latter being the proposed attachment site of the polysaccharide. The structural variability seen in these three lipids A was unusual for a single species and may have consequences for the pathogenicity of this Bordetella species.Bordetella bronchiseptica is a respiratory tract pathogen of mammals causing a whooping cough syndrome milder than that due to Bordetella pertussis in humans. This bacterium causes bronchopneumonia in rabbits and guinea pigs, kennel cough in dogs, and atrophic rhinitis in piglets (13). Recently, it has been described as responsible for bronchopneumonia in human immunosuppressed patients (1, 27, 28) and in at least two immunocompetent patients, one of whom was exposed to infected animals (14). Its endotoxin, a mixture of lipopolysaccharides (LPSs), which are a major component of the bacterial outer membrane, has been implicated as a virulence factor. B. bronchiseptica, like Bordetella parapertussis, produces smoothtype LPSs. Their O chains have identical structures (11). B. pertussis LPSs, which are of the rough type, have been analyzed, and their structures have recently become available (4,6,25). Structural variability in parts of LPS other than the O chains may thus relate to pathogenicity or to host specificity. We report here the detailed structural characterization of the lipid A moieties of three different strains of B. bronchiseptica grown under the same culture conditions and show that they have greater variability than that usually encountered in a single species. MATERIALS AND METHODSMass spectrometry. Plasma desorption mass (PDM) spectra were obtained with a Depil TOF 21 mass spectrometer (10). Flight distance was 90 cm, acceleration voltage was ϩ15 or Ϫ15 kV, an...

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Section: Methodsmentioning

confidence: 99%

Structural characterization of the lipids A of three Bordetella bronchiseptica strains: variability of fatty acid substitution

et al. 1997

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“…Hydroxylaminolysis of lipid A or LPS (31) followed by carbomethylation (37) and analysis of the liberated fatty acids by gas chromatography and mass spectrometry (23) showed that the 3-OH C10, the C14, and one-third of the 3-OH C14 were in ester linkage; treatment with 0.1 M sodium hydroxide at 37°C for 30 min, which liberates esterified substituents on the C-3 position of each glucosamine, showed that these positions held the hydroxydecanoic acid and one hydroxytetradecanoic acid. The Kraska method (19), as modified by Wollenweber and Rietschel (37), revealed that the tetradecanoic acids acylated one of the two hydroxytetradecanoates in amide position.…”

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confidence: 99%

Structural characterization of the lipid A of Bordetella pertussis 1414 endotoxin

et al. 1994

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The structure of Bordetefla pertussis 1414 lipid A was investigated by classical methods of chemical analysis as well as plasma desorption mass spectrometry and fast atom bombardment mass spectrometry. Previous analysis showed that it contained a bisphosphorylated II-(1-6)-linked D-glucosamine disaccharide with hydroxytetradecanoic acid in amide linkage. The presence of two main molecular species as seen by thin-layer chromatography was confirmed by plasma desorption mass spectrometry, in which the larger signal was attributable to a molecular ion containing two glucosamine, two phosphate, one tetradecanoic acid, one hydroxydecanoic acid, and three hydroxytetradecanoic acid residues. The ion of the smaller signal was lighter by the mass of one hydroxytetradecanoic acid residue (226 Da). The fatty acids in ester linkage were localized by chemical and fast atom bombardment mass spectrometry analysis. C-4 and C-6' hydroxyl groups of the backbone disaccharide were unsubstituted, the latter being the proposed attachment site for Kdo (3-deoxy-Dmanno-octulosonic acid).Endotoxins are major constituents of the outer membrane of gram-negative bacteria. Their main interest lies in the many biological activities they induce even at low doses. They are ensembles of related lipopolysaccharides (LPS) consisting of a lipid moiety, termed lipid A, linked to a polysaccharide chain of variable length.The biological activities and serological relationships of the endotoxins of various Bordetella species have been explored in the light of the variations in the diseases they cause (1, 35).Recently, the relationship between Bordetella parapertussis and Bordetella bronchiseptica was clarified by the finding that their O chains were identical although their core regions were different (13). The serological properties of the rough-type endotoxin of Bordetella pertussis, the agent of whooping cough, have been well documented, and the determination of its complex glycosidic structure is nearing completion (2,5,12,14,20,22,27).The lipid moiety of B. pertussis LPS, like that of other endotoxins, is responsible for most of the biological activities of the molecule (11). Early work indicated a backbone structure identical to that of enteric bacteria, i.e., a B-1i',6-linked diglucosamine phosphorylated on the a-glycosidic and 4' carbons and the two glucosamines amidated by 3-hydroxytetradecanoic acid (9, 15). However, it differs from the lipid A of enteric organisms in that it contains only two or three esterlinked fatty acids, instead of three to five, and one of those is hydroxydecanoic acid (8,11). With this information, it was possible, by the use of plasma desorption mass spectrometry (PDMS), to determine how many molecular species were present in a preparation and the composition and relative abundance of each (18). These results are presented here together with nuclear magnetic resonance (NMR) confirmation of the C-4' position of the glucosamine II The B. pertussis endotoxin used in this work was prepared by hot phenol-water extraction...

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Analysis of permethylated glucosaminyl-glucosaminitol disaccharides by combined gas-liquid chromatography mass spectrometry

Jensen

Borowiak

Paulsen

et al. 1979

Biol. Mass Spectrom.

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The α‐and β‐forms of permethylated 1,3‐, 1,4‐ and 1,6‐linked N‐acetylglucosaminyl‐N‐acetylglucosaminitol disaccharides have been analysed directly (without hydrolysis or further modifications) by combined gas‐liquid chromatography mass spectrometry. Gas‐liquid chromatography facilitated the separation of the α‐ and β‐isomers of each disaccharide pair. In every case, the respective α‐form was slower than the β‐form. While, additionally, the α‐ and β‐forms of the 1,6‐linked glucosamine disaccharide could be separated from those of the 1,3‐ and 1,4‐linked disaccharides, the α‐ and β‐forms of the latter two could not be resolved from each other with the liquid phases used. All three disaccharides could be readily differentiated and characterized by mass spectrometry, however. Specific fragments for each glucosamine disaccharide could be defined. Therefore, combined gas‐liquid chromatography mass spectrometry allowed an unequivocal determination of the anomeric configuration and the position of the glycosidic linkage in the glucosamine disaccharides.

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Mēthylation de dērivēs n-acylēs du 2-amino-2-dēsoxy-D-glucose en prēsence de sels d'argent: observations sur le comportement du groupement ambident acetamido (ou benzamido)

Cited by 21 publications

References 21 publications

Structural characterization of the lipids A of three Bordetella bronchiseptica strains: variability of fatty acid substitution

Structural characterization of the lipids A of three Bordetella bronchiseptica strains: variability of fatty acid substitution

Structural characterization of the lipid A of Bordetella pertussis 1414 endotoxin

Analysis of permethylated glucosaminyl-glucosaminitol disaccharides by combined gas-liquid chromatography mass spectrometry

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