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. 1991 Jan;173(2):618–626. doi: 10.1128/jb.173.2.618-626.1991

Chemical characterization of Campylobacter jejuni lipopolysaccharides containing N-acetylneuraminic acid and 2,3-diamino-2,3-dideoxy-D-glucose.

A P Moran 1, E T Rietschel 1, T U Kosunen 1, U Zähringer 1
PMCID: PMC207052  PMID: 1987154

Abstract

Lipopolysaccharides (LPS) of four nonencapsulated strains of the human enteric pathogen Campylobacter jejuni were chemically characterized. When applied to two of the strains, extraction by a modified phenol-chloroform-petroleum ether method (H. Brade and C. Galanos, Eur. J. Biochem. 122:233-237, 1982) gave better yields of LPS than did extraction by the conventional hot phenol-water technique. Constituents common to all LPS were D-glucose, D-galactose, L-glycero-D-manno-heptose, 3-deoxy-D-manno-2-octulosonic acid, D-glucuronic acid, D-galactosamine, and phosphorylethanolamine. Phosphate was present in a relatively high amount. In addition, the LPS of three strains contained N-acetylneuraminic acid, whereas the LPS of the strain lacking this component contained 3-amino-3,6-dideoxy-D-glucose. The lipid A component contained phosphate with D-glucosamine and 2,3-diamino-2,3-dideoxy-D-glucose as the major amino sugars. Ethanolamine-phosphate was present also. The major fatty acids were ester- and amide-bound 3-hydroxytetradecanoic and ester-bound hexadecanoic acids, with a minor amount of ester-bound tetradecanoic acid. This is the first report of N-acetylneuraminic acid in the oligosaccharide moiety and diaminoglucose in the lipid A of C. jejuni LPS.

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Selected References

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  1. BITTER T., MUIR H. M. A modified uronic acid carbazole reaction. Anal Biochem. 1962 Oct;4:330–334. doi: 10.1016/0003-2697(62)90095-7. [DOI] [PubMed] [Google Scholar]
  2. Beer W., Adam M., Seltmann G. Monosaccharide composition of lipopolysaccharides from Campylobacter jejuni and Campylobacter coli. J Basic Microbiol. 1986;26(4):201–204. doi: 10.1002/jobm.3620260405. [DOI] [PubMed] [Google Scholar]
  3. Blaser M. J., Perez G. P., Smith P. F., Patton C., Tenover F. C., Lastovica A. J., Wang W. I. Extraintestinal Campylobacter jejuni and Campylobacter coli infections: host factors and strain characteristics. J Infect Dis. 1986 Mar;153(3):552–559. doi: 10.1093/infdis/153.3.552. [DOI] [PubMed] [Google Scholar]
  4. Blaser M. J., Reller L. B. Campylobacter enteritis. N Engl J Med. 1981 Dec 10;305(24):1444–1452. doi: 10.1056/NEJM198112103052404. [DOI] [PubMed] [Google Scholar]
  5. Brade H., Brade L., Rietschel E. T. Structure-activity relationships of bacterial lipopolysaccharides (endotoxins). Current and future aspects. Zentralbl Bakteriol Mikrobiol Hyg A. 1988 Apr;268(2):151–179. doi: 10.1016/s0176-6724(88)80001-4. [DOI] [PubMed] [Google Scholar]
  6. Brade H., Galanos C. A method to detect 2-keto-3-deoxyoctanat and related compounds on pherograms and chromatograms. Anal Biochem. 1983 Jul 1;132(1):158–159. doi: 10.1016/0003-2697(83)90440-2. [DOI] [PubMed] [Google Scholar]
  7. Brade H., Galanos C. Isolation, purification, and chemical analysis of the lipopolysaccharide and lipid A of Acinetobacter calcoaceticus NCTC 10305. Eur J Biochem. 1982 Feb;122(2):233–237. doi: 10.1111/j.1432-1033.1982.tb05871.x. [DOI] [PubMed] [Google Scholar]
  8. Dawson C. R., Jones D. B., Kaufman H. E., Barron B. A., Hauck W. W., Wilhelmus K. R. Design and organization of the herpetic eye disease study (HEDS). Curr Eye Res. 1991;10 (Suppl):105–110. doi: 10.3109/02713689109020365. [DOI] [PubMed] [Google Scholar]
  9. HAKOMORI S. A RAPID PERMETHYLATION OF GLYCOLIPID, AND POLYSACCHARIDE CATALYZED BY METHYLSULFINYL CARBANION IN DIMETHYL SULFOXIDE. J Biochem. 1964 Feb;55:205–208. [PubMed] [Google Scholar]
  10. HANES C. S., ISHERWOOD F. A. Separation of the phosphoric esters on the filter paper chromatogram. Nature. 1949 Dec 31;164(4183):1107-12, illust. doi: 10.1038/1641107a0. [DOI] [PubMed] [Google Scholar]
  11. 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]
  12. Hase S., Rietschel E. T. Isolation and analysis of the lipid A backbone. Lipid A structure of lipopolysaccharides from various bacterial groups. Eur J Biochem. 1976 Mar 16;63(1):101–107. doi: 10.1111/j.1432-1033.1976.tb10212.x. [DOI] [PubMed] [Google Scholar]
  13. Helander I. M., Lindner B., Brade H., Altmann K., Lindberg A. A., Rietschel E. T., Zähringer U. Chemical structure of the lipopolysaccharide of Haemophilus influenzae strain I-69 Rd-/b+. Description of a novel deep-rough chemotype. Eur J Biochem. 1988 Nov 15;177(3):483–492. doi: 10.1111/j.1432-1033.1988.tb14398.x. [DOI] [PubMed] [Google Scholar]
  14. Jann K., Jann B. Polysaccharide antigens of Escherichia coli. Rev Infect Dis. 1987 Sep-Oct;9 (Suppl 5):S517–S526. doi: 10.1093/clinids/9.supplement_5.s517. [DOI] [PubMed] [Google Scholar]
  15. Kasai N., Arata S., Mashimo J., Akiyama Y., Tanaka C., Egawa K., Tanaka S. Pseudomonas diminuta LPS with a new endotoxic lipid A structure. Biochem Biophys Res Commun. 1987 Feb 13;142(3):972–978. doi: 10.1016/0006-291x(87)91509-9. [DOI] [PubMed] [Google Scholar]
  16. Kedzierska B. N-Acetylneuraminic acid: a constituent of the lipopolysaccharide of Salmonella toucra. Eur J Biochem. 1978 Nov 15;91(2):545–552. doi: 10.1111/j.1432-1033.1978.tb12708.x. [DOI] [PubMed] [Google Scholar]
  17. Kondo S., Zähringer U. Identification of 2-acetamido-3-O-(3-acetamido-3,6-dideoxy-beta-D-glucopyranosyl)-2-deoxy -D-galactopyranose isolated after degradation of the lipopolysaccharide from Vibrio parahaemolyticus serotype O12. Carbohydr Res. 1990 Feb 25;196:191–197. doi: 10.1016/0008-6215(90)84119-f. [DOI] [PubMed] [Google Scholar]
  18. LOWRY O. H., ROBERTS N. R., LEINER K. Y., WU M. L., FARR A. L. The quantitative histochemistry of brain. I. Chemical methods. J Biol Chem. 1954 Mar;207(1):1–17. [PubMed] [Google Scholar]
  19. Lau P. P., DeBrunner-Vossbrinck B., Dunn B., Miotto K., MacDonnell M. T., Rollins D. M., Pillidge C. J., Hespell R. B., Colwell R. R., Sogin M. L. Phylogenetic diversity and position of the genus Campylobacter. Syst Appl Microbiol. 1987;9:231–238. doi: 10.1016/s0723-2020(87)80027-9. [DOI] [PubMed] [Google Scholar]
  20. Lüderitz O., Ruschmann E., Westphal O., Raff R., Wheat R. Occurrence of 3-amino-3,6-dideoxyhexoses in Salmonella and related bacteria. J Bacteriol. 1967 May;93(5):1681–1687. doi: 10.1128/jb.93.5.1681-1687.1967. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. McSweegan E., Walker R. I. Identification and characterization of two Campylobacter jejuni adhesins for cellular and mucous substrates. Infect Immun. 1986 Jul;53(1):141–148. doi: 10.1128/iai.53.1.141-148.1986. [DOI] [PMC free article] [PubMed] [Google Scholar]
  22. Mills S. D., Bradbury W. C., Penner J. L. Basis for serological heterogeneity of thermostable antigens of Campylobacter jejuni. Infect Immun. 1985 Oct;50(1):284–291. doi: 10.1128/iai.50.1.284-291.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  23. Moran A. P., Kosunen T. U. Serological analysis of the heat-stable antigens involved in serotyping Campylobacter jejuni and Campylobacter coli. APMIS. 1989 Mar;97(3):253–260. [PubMed] [Google Scholar]
  24. Naess V., Hofstad T. Chemical composition and biological activity of lipopolysaccharides prepared from type strains of Campylobacter jejuni and Campolybacter coli. Acta Pathol Microbiol Immunol Scand B. 1984 Aug;92(4):217–222. doi: 10.1111/j.1699-0463.1984.tb02824.x. [DOI] [PubMed] [Google Scholar]
  25. Naess V., Hofstad T. Chemical studies of partially hydrolysed lipopolysaccharides from four strains of Campylobacter jejuni and two strains of Campylobacter coli. J Gen Microbiol. 1984 Nov;130(11):2783–2789. doi: 10.1099/00221287-130-11-2783. [DOI] [PubMed] [Google Scholar]
  26. Naess V., Hofstad T. Isolation and chemical composition of lipopolysaccharide from Campylobacter jejuni. Acta Pathol Microbiol Immunol Scand B. 1982 Apr;90(2):135–139. doi: 10.1111/j.1699-0463.1982.tb00095.x. [DOI] [PubMed] [Google Scholar]
  27. Parsons N. J., Andrade J. R., Patel P. V., Cole J. A., Smith H. Sialylation of lipopolysaccharide and loss of absorption of bactericidal antibody during conversion of gonococci to serum resistance by cytidine 5'-monophospho-N-acetyl neuraminic acid. Microb Pathog. 1989 Jul;7(1):63–72. doi: 10.1016/0882-4010(89)90112-5. [DOI] [PubMed] [Google Scholar]
  28. Preston M. A., Penner J. L. Structural and antigenic properties of lipopolysaccharides from serotype reference strains of Campylobacter jejuni. Infect Immun. 1987 Aug;55(8):1806–1812. doi: 10.1128/iai.55.8.1806-1812.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  29. Rautelin H. I., Renkonen O. V., von Bonsdorff C. H., Lähdevirta J., Pitkänen T., Järvinen A., Reinikainen P., Kosunen T. U. Prospective study of the etiology of diarrhea in adult outpatients and inpatients. Scand J Gastroenterol. 1989 Apr;24(3):329–333. doi: 10.3109/00365528909093055. [DOI] [PubMed] [Google Scholar]
  30. Rietschel E. T., Gottert H., Lüderitz O., Westphal O. Nature and linkages of the fatty acids present in the lipid-A component of Salmonella lipopolysaccharides. Eur J Biochem. 1972 Jul 13;28(2):166–173. doi: 10.1111/j.1432-1033.1972.tb01899.x. [DOI] [PubMed] [Google Scholar]
  31. Romaniuk P. J., Zoltowska B., Trust T. J., Lane D. J., Olsen G. J., Pace N. R., Stahl D. A. Campylobacter pylori, the spiral bacterium associated with human gastritis, is not a true Campylobacter sp. J Bacteriol. 1987 May;169(5):2137–2141. doi: 10.1128/jb.169.5.2137-2141.1987. [DOI] [PMC free article] [PubMed] [Google Scholar]
  32. Roppel J., Mayer H. Identification of a 2, 3-diamino-2, 3-dideoxyhexose in the lipid A component of lipopolysaccharides of Rhodopseudomonas viridis and Rhodopseudomonas palustris. Carbohydr Res. 1975 Mar;40(1):31–40. doi: 10.1016/s0008-6215(00)82666-x. [DOI] [PubMed] [Google Scholar]
  33. STROMINGER J. L., PARK J. T., THOMPSON R. E. Composition of the cell wall of Staphylococcus aureus: its relation to the mechanism of action of penicillin. J Biol Chem. 1959 Dec;234:3263–3268. [PubMed] [Google Scholar]
  34. Seltmann G., Beer W. Vorkommen von 3-Amino-3,6-didesoxy-D-glucose in einem Lipopolysaccharid von Campylobacter coli. J Basic Microbiol. 1985;25(8):551–552. doi: 10.1002/jobm.3620250823. [DOI] [PubMed] [Google Scholar]
  35. Sidorczyk Z., Zähringer U., Rietschel E. T. Chemical structure of the lipid A component of the lipopolysaccharide from a Proteus mirabilis Re-mutant. Eur J Biochem. 1983 Dec 1;137(1-2):15–22. doi: 10.1111/j.1432-1033.1983.tb07789.x. [DOI] [PubMed] [Google Scholar]
  36. TREVELYAN W. E., PROCTER D. P., HARRISON J. S. Detection of sugars on paper chromatograms. Nature. 1950 Sep 9;166(4219):444–445. doi: 10.1038/166444b0. [DOI] [PubMed] [Google Scholar]
  37. WARAVDEKAR V. S., SASLAW L. D. A sensitive colorimetric method for the estimation of 2-deoxy sugars with the use of the malonaldehyde-thiobarbituric acid reaction. J Biol Chem. 1959 Aug;234(8):1945–1950. [PubMed] [Google Scholar]
  38. Weckesser J., Mayer H. Different lipid A types in lipopolysaccharides of phototrophic and related non-phototrophic bacteria. FEMS Microbiol Rev. 1988 Apr-Jun;4(2):143–153. doi: 10.1111/j.1574-6968.1988.tb02740.x. [DOI] [PubMed] [Google Scholar]
  39. Wilkinson S. G., Taylor D. P. Occurrence of 2,3-diamino-2,3-dideoxy-d-glucose in lipid A from lipopolysaccharide of pseudomonas diminuta. J Gen Microbiol. 1978 Dec;109(2):367–370. doi: 10.1099/00221287-109-2-367. [DOI] [PubMed] [Google Scholar]

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