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. 1994 Aug;176(16):5156–5159. doi: 10.1128/jb.176.16.5156-5159.1994

Structural characterization of the lipid A of Bordetella pertussis 1414 endotoxin.

M Caroff 1, C Deprun 1, J C Richards 1, D Karibian 1
PMCID: PMC196360  PMID: 8051033

Abstract

The structure of Bordetella 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 beta-(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-D-manno-octulosonic acid).

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Selected References

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  1. Amano K., Fukushi K., Watanabe M. Biochemical and immunological comparison of lipopolysaccharides from Bordetella species. J Gen Microbiol. 1990 Mar;136(3):481–487. doi: 10.1099/00221287-136-3-481. [DOI] [PubMed] [Google Scholar]
  2. Archambault D., Rondeau P., Martin D., Brodeur B. R. Characterization and comparative bactericidal activity of monoclonal antibodies to Bordetella pertussis lipo-oligosaccharide A. J Gen Microbiol. 1991 Apr;137(4):905–911. doi: 10.1099/00221287-137-4-905. [DOI] [PubMed] [Google Scholar]
  3. Caroff M., Chaby R., Karibian D., Perry J., Deprun C., Szabó L. Variations in the carbohydrate regions of Bordetella pertussis lipopolysaccharides: electrophoretic, serological, and structural features. J Bacteriol. 1990 Feb;172(2):1121–1128. doi: 10.1128/jb.172.2.1121-1128.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Caroff M., Deprun C., Karibian D. 252Cf plasma desorption mass spectrometry applied to the analysis of underivatized rough-type endotoxin preparations. J Biol Chem. 1993 Jun 15;268(17):12321–12324. [PubMed] [Google Scholar]
  5. Caroff M., Deprun C., Karibian D., Szabó L. Analysis of unmodified endotoxin preparations by 252Cf plasma desorption mass spectrometry. Determination of molecular masses of the constituent native lipopolysaccharides. J Biol Chem. 1991 Oct 5;266(28):18543–18549. [PubMed] [Google Scholar]
  6. Caroff M., Szabó L. Identification of 2-amino-6-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D-glucose as a major constituent of the hydrophobic region of the Bordetella pertussis endotoxin. Carbohydr Res. 1983 Mar 16;114(1):95–102. doi: 10.1016/0008-6215(83)88176-2. [DOI] [PubMed] [Google Scholar]
  7. Caroff M., Tacken A., Szabó L. Detergent-accelerated hydrolysis of bacterial endotoxins and determination of the anomeric configuration of the glycosyl phosphate present in the "isolated lipid A" fragment of the Bordetella pertussis endotoxin. Carbohydr Res. 1988 Apr 15;175(2):273–282. doi: 10.1016/0008-6215(88)84149-1. [DOI] [PubMed] [Google Scholar]
  8. Di Fabio J. L., Caroff M., Karibian D., Richards J. C., Perry M. B. Characterization of the common antigenic lipopolysaccharide O-chains produced by Bordetella bronchiseptica and Bordetella parapertussis. FEMS Microbiol Lett. 1992 Oct 15;76(3):275–281. doi: 10.1016/0378-1097(92)90348-r. [DOI] [PubMed] [Google Scholar]
  9. Finger H., Heymer B., Hof H., Rietschel E., Schleifer K. H. Uber Struktur und biologische Aktivität von Bordetella pertussis-Endotoxin. Zentralbl Bakteriol Orig A. 1976 Aug;235(1-3):56–64. [PubMed] [Google Scholar]
  10. Haeffner N., Chaby R., Szabó L. Identification of 2-methyl-3-hydroxydecanoic and 2-methyl-3-hydroxytetradecanoic acids in the 'lipid X' fraction of the Bordetella pertussis endotoxin. Eur J Biochem. 1977 Aug 1;77(3):535–544. doi: 10.1111/j.1432-1033.1977.tb11696.x. [DOI] [PubMed] [Google Scholar]
  11. Helander I. M., Hirvas L., Tuominen J., Vaara M. Preferential synthesis of heptaacyl lipopolysaccharide by the ssc permeability mutant of Salmonella typhimurium. Eur J Biochem. 1992 Mar 15;204(3):1101–1106. doi: 10.1111/j.1432-1033.1992.tb16734.x. [DOI] [PubMed] [Google Scholar]
  12. Karibian D., Deprun C., Caroff M. Comparison of lipids A of several Salmonella and Escherichia strains by 252Cf plasma desorption mass spectrometry. J Bacteriol. 1993 May;175(10):2988–2993. doi: 10.1128/jb.175.10.2988-2993.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Lebbar S., Caroff M., Szabó L., Mérienne C., Szilógyi L. Structure of a hexasaccharide proximal to the hydrophobic region of lipopolysaccharides present in Bordetella pertussis endotoxin preparations. Carbohydr Res. 1994 Jun 17;259(2):257–275. doi: 10.1016/0008-6215(94)84061-x. [DOI] [PubMed] [Google Scholar]
  14. Loppnow H., Brade H., Dürrbaum I., Dinarello C. A., Kusumoto S., Rietschel E. T., Flad H. D. IL-1 induction-capacity of defined lipopolysaccharide partial structures. J Immunol. 1989 May 1;142(9):3229–3238. [PubMed] [Google Scholar]
  15. Martin D., Peppler M. S., Brodeur B. R. Immunological characterization of the lipooligosaccharide B band of Bordetella pertussis. Infect Immun. 1992 Jul;60(7):2718–2725. doi: 10.1128/iai.60.7.2718-2725.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Masoud H., Perry M. B., Richards J. C. Characterization of the lipopolysaccharide of Moraxella catarrhalis. Structural analysis of the lipid A from M. catarrhalis serotype A lipopolysaccharide. Eur J Biochem. 1994 Feb 15;220(1):209–216. doi: 10.1111/j.1432-1033.1994.tb18616.x. [DOI] [PubMed] [Google Scholar]
  17. Peppler M. S. Two physically and serologically distinct lipopolysaccharide profiles in strains of Bordetella pertussis and their phenotype variants. Infect Immun. 1984 Jan;43(1):224–232. doi: 10.1128/iai.43.1.224-232.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Raetz C. R. Biochemistry of endotoxins. Annu Rev Biochem. 1990;59:129–170. doi: 10.1146/annurev.bi.59.070190.001021. [DOI] [PubMed] [Google Scholar]
  19. Ray A., Redhead K., Selkirk S., Poole S. Variability in LPS composition, antigenicity and reactogenicity of phase variants of Bordetella pertussis. FEMS Microbiol Lett. 1991 Apr 15;63(2-3):211–217. doi: 10.1016/0378-1097(91)90088-r. [DOI] [PubMed] [Google Scholar]
  20. Rottem S., Markowitz O., Razin S. Thermal regulation of the fatty acid composition of lipopolysaccharides and phospholipids of Proteus mirabilis. Eur J Biochem. 1978 Apr 17;85(2):445–450. doi: 10.1111/j.1432-1033.1978.tb12258.x. [DOI] [PubMed] [Google Scholar]
  21. Rutherford G., Morgan A. R. The specific chemical cleavage of pyrophosphate diesters. Can J Biochem. 1972 Mar;50(3):287–291. doi: 10.1139/o72-040. [DOI] [PubMed] [Google Scholar]
  22. SNYDER F., STEPHENS N. A simplified spectrophotometric determination of ester groups in lipids. Biochim Biophys Acta. 1959 Jul;34:244–245. doi: 10.1016/0006-3002(59)90255-0. [DOI] [PubMed] [Google Scholar]
  23. Takada H., Kotani S. Structural requirements of lipid A for endotoxicity and other biological activities. Crit Rev Microbiol. 1989;16(6):477–523. doi: 10.3109/10408418909104475. [DOI] [PubMed] [Google Scholar]
  24. Volk W. A., Galanos C., Lüderitz O. The occurrence of 4-amino-4-deoxy-L-arabinose as a constituent in Salmonella lipopolysaccharide preparations. Eur J Biochem. 1970 Dec;17(2):223–229. doi: 10.1111/j.1432-1033.1970.tb01157.x. [DOI] [PubMed] [Google Scholar]
  25. Watanabe M., Takimoto H., Kumazawa Y., Amano K. Biological properties of lipopolysaccharides from Bordetella species. J Gen Microbiol. 1990 Mar;136(3):489–493. doi: 10.1099/00221287-136-3-489. [DOI] [PubMed] [Google Scholar]

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