Skip to main content
NCBI home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1982 Apr;150(1):27–35. doi: 10.1128/jb.150.1.27-35.1982

Isolation of a trisaccharide containing 2-amino-2-deoxy-D-galacturonic acid from the Bordetella pertussis endotoxin.

M Moreau, R Chaby, L Szabo
PMCID: PMC220078  PMID: 6277864

Abstract

4-O-(2-Amino-2-deoxy-alpha-D-glucopyranosyl-6-O-(2-amino-2-deoxy-alpha-D-galactopyranuronyl)-D-glucopyranose, a branched-chain trisaccharide, was isolated after hydrolysis of Bordetella pertussis endotoxin with 4 M HCl for 1 h at 100 degrees C. The trisaccharide was present in both polysaccharide moieties of the two constituent lipopolysaccharides of this endotoxin. Its structure was established by analysis of the 400-MHz nuclear magnetic resonance spectrum and by chemical and enzymatic degradation.

Full text

PDF
27

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Aprile M. A., Wardlaw A. C. Immunochemical studies on the lipopolysaccharides of Bordetella pertussis. Can J Microbiol. 1973 Feb;19(2):231–239. doi: 10.1139/m73-035. [DOI] [PubMed] [Google Scholar]
  2. Dische Z., Danilchenko A. Modifications of two color reactions of hexoses with cysteine and sulfuric acid. Anal Biochem. 1967 Oct;21(1):119–124. doi: 10.1016/0003-2697(67)90090-5. [DOI] [PubMed] [Google Scholar]
  3. Hase S., Matsushima Y. Structural studies on a glucose containing polysaccharide obtained from Micrococcus lysodeikticus cell walls. I. J Biochem. 1970 Nov;68(5):723–730. doi: 10.1093/oxfordjournals.jbchem.a129406. [DOI] [PubMed] [Google Scholar]
  4. Kontrohr T. The identification of 2-amino-2-deoxy-L-altruronic acid as a constituent of Shigella sonnei phase I lipopolysaccharide. Carbohydr Res. 1977 Oct;58(2):498–500. doi: 10.1016/s0008-6215(00)84379-7. [DOI] [PubMed] [Google Scholar]
  5. LEVVY G. A., MCALLAN A. The N-acetylation and estimation of hexosamines. Biochem J. 1959 Sep;73:127–132. doi: 10.1042/bj0730127. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Le Dur A., Chaby R., Szabó L. Isolation of two protein-free and chemically different lipopolysaccharides from Bordetella pertussis phenol-extracted endotoxin. J Bacteriol. 1980 Jul;143(1):78–88. doi: 10.1128/jb.143.1.78-88.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Liau D. F., Hash J. H. Structural analysis of the surface polysaccharide of Staphylococcus aureus M. J Bacteriol. 1977 Jul;131(1):194–200. doi: 10.1128/jb.131.1.194-200.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Listowsky I., Englard S., Avigad G. An analysis of the circular dichroism spectra of uronic acids. Biochemistry. 1969 May;8(5):1781–1785. doi: 10.1021/bi00833a001. [DOI] [PubMed] [Google Scholar]
  9. MACLENNAN A. P. Specific lipopolysaccharides of Bordetella. Biochem J. 1960 Feb;74:398–409. doi: 10.1042/bj0740398. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Mayer H. D-Mannosaminuronsäure-Baustein des K7-antigens von Escherichia coli. Eur J Biochem. 1969 Mar;8(1):139–145. doi: 10.1111/j.1432-1033.1969.tb00506.x. [DOI] [PubMed] [Google Scholar]
  11. Morrison G. R. Microchemical determination of organic nitrogen with Nessler reagent. Anal Biochem. 1971 Oct;43(2):527–532. doi: 10.1016/0003-2697(71)90283-1. [DOI] [PubMed] [Google Scholar]
  12. Männel D., Mayer H. Isolation and chemical characterization of the enterobacterial common antigen. Eur J Biochem. 1978 May 16;86(2):361–370. doi: 10.1111/j.1432-1033.1978.tb12318.x. [DOI] [PubMed] [Google Scholar]
  13. PERKINS H. R. A polymer containing glucose and aminohexuronic acid isolated from the cell walls of micrococcus lysodeikticus. Biochem J. 1963 Mar;86:475–483. doi: 10.1042/bj0860475. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. RONDLE C. J., MORGAN W. T. The determination of glucosamine and galactosamine. Biochem J. 1955 Dec;61(4):586–589. doi: 10.1042/bj0610586. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Raff R. A., Wheat R. W. Carbohydrate composition of the phenol-soluble lipopolysaccharides of Citrobacter freundii. J Bacteriol. 1968 Jun;95(6):2035–2043. doi: 10.1128/jb.95.6.2035-2043.1968. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. STOFFYN P. J., JEANLOZ R. W. Identification of amino sugars by paper chromatography. Arch Biochem Biophys. 1954 Oct;52(2):373–379. doi: 10.1016/0003-9861(54)90137-x. [DOI] [PubMed] [Google Scholar]
  17. Sandford P. A., Watson P. R., Jeanes A. R. An extracellular microbial polysaccharide composed of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-glucuronic acid: radiochemical and gas-chromatographic analysis of the products of methanolysis. Carbohydr Res. 1973 Jul;29(1):153–164. doi: 10.1016/s0008-6215(00)82079-0. [DOI] [PubMed] [Google Scholar]
  18. Smith E. J. Purification and properties of an acidic polysaccharide isolated from Achromobacter georgiopolitanum. J Biol Chem. 1968 Oct 10;243(19):5139–5144. [PubMed] [Google Scholar]
  19. 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]
  20. Torii M., Sakakibara K., Kuroda K. Occurrence of 2-amino-2-deoxy-hexuronic acids as constituents of Vibrio parahaemolyticus K15 antigen. Eur J Biochem. 1973 Sep 3;37(3):401–405. doi: 10.1111/j.1432-1033.1973.tb02999.x. [DOI] [PubMed] [Google Scholar]
  21. WILLIAMSON A. R., ZAMENHOF S. The type-specific substance of Hemophilus influenzae, type d: the natural occurrence of glucosamine uronic acid. J Biol Chem. 1963 Jul;238:2255–2258. [PubMed] [Google Scholar]
  22. Weckesser J., Drews G., Roppel J., Mayer H., Fromme I. The lipopolysaccharides (O-antigens) of Rhodopseudomonas viridis. Arch Microbiol. 1974;101(3):233–245. doi: 10.1007/BF00455941. [DOI] [PubMed] [Google Scholar]
  23. Wilkinson S. G., Welbourn A. P. 2-Amino-2-deoxygalacturonic acid in lipopolysaccharides from Pseudomonas aerugimosa. Biochem J. 1975 Sep;149(3):783–784. doi: 10.1042/bj1490783. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES