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. 1977 Jan 1;161(1):103–109. doi: 10.1042/bj1610103

Amino components of the lipopolysaccharide from Pseudomonas aeruginosa N.C.T.C. 8505. Presence of 2,4-diamino-2,4,6-trideoxy-D-glucose.

S G Wilkinson
PMCID: PMC1164478  PMID: 403906

Abstract

Configurations were determined for previously identified amino components of the lipopolysaccharide from Pseudomonas aeruginosa N.C.T.C. 8505. Glucosamine and galactosamine belong to the D-series, and alanine and aminogalacturonic acid to the L-series. An additional amino component was identified as 2,4-diamino-2,4,6-trideoxy-D-glucose. This compound may be a characteristic component of the O-specific chain in lipopolysaccharides of strains of Pseudomonas aeruginosa belonging to Habs sero-group 3.

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Selected References

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

  1. Ashwell G., Brown N. C., Volk W. A. A colorimetric procedure for the determination of N-acetylated-3-amino hexoses. Arch Biochem Biophys. 1965 Dec;112(3):648–652. doi: 10.1016/0003-9861(65)90108-6. [DOI] [PubMed] [Google Scholar]
  2. Brownlee S. T., Wheat R. W. On the determination of galactosamine-uronic acid. Anal Biochem. 1966 Mar;14(3):414–420. doi: 10.1016/0003-2697(66)90283-1. [DOI] [PubMed] [Google Scholar]
  3. Brundish D. E., Baddiley J. Pneumococcal C-substance, a ribitol teichoic acid containing choline phosphate. Biochem J. 1968 Dec;110(3):573–582. doi: 10.1042/bj1100573. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. CHARALAMPOUS F. C., MUELLER G. C. Synthesis of erythrulose phosphate by a soluble enzyme from rat liver. J Biol Chem. 1953 Mar;201(1):161–173. [PubMed] [Google Scholar]
  5. CRUMPTON M. J. Identification of amino sugars. Biochem J. 1959 Jul;72:479–486. doi: 10.1042/bj0720479. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Chester I. R., Meadow P. M. Heterogeneity of the lipopolysaccharide from Pseudomonas aeruginosa. Eur J Biochem. 1975 Oct 15;58(2):273–282. doi: 10.1111/j.1432-1033.1975.tb02373.x. [DOI] [PubMed] [Google Scholar]
  7. Chester I. R., Meadow P. M., Pitt T. L. The relationship between the O-antigenic lipopolysaccharides and serological specificity in strains of Pseudomonas aeruginosa of different O-serotypes. J Gen Microbiol. 1973 Oct;78(2):305–318. doi: 10.1099/00221287-78-2-305. [DOI] [PubMed] [Google Scholar]
  8. Distler J., Kaufman B., Roseman S. Enzymic synthesis of a diamino sugar nucleotide by extracts of type XIV Diplococcus pneumoniae. Arch Biochem Biophys. 1966 Sep 26;116(1):466–478. doi: 10.1016/0003-9861(66)90054-3. [DOI] [PubMed] [Google Scholar]
  9. Drewry D. T., Symes K. C., Gray G. W., Wilkinson S. G. Studies of polysaccharide fractions from the lipopolysaccharide of Pseudomonas aeruginosa N.C.T.C. 1999. Biochem J. 1975 Jul;149(1):93–106. doi: 10.1042/bj1490093. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Gmeiner J. The isolation of two different lipopolysaccharide fractions from various Proteus mirabilis strains. Eur J Biochem. 1975 Oct 15;58(2):621–626. doi: 10.1111/j.1432-1033.1975.tb02413.x. [DOI] [PubMed] [Google Scholar]
  11. Griggs L. J., Post A., White E. R., Finkelstein J. A., Moeckel W. E., Holden K. G., Zarembo J. E., Weisbach J. A. Identification and quantitation of alditol acetates of neutral and amino sugars from mucins by automated gas-liquid chromatography. Anal Biochem. 1971 Oct;43(2):369–381. doi: 10.1016/0003-2697(71)90266-1. [DOI] [PubMed] [Google Scholar]
  12. Jann B., Jann K. 4-amino-4,6-dideoxyhexoses isolated from lipopolysaccharides of Escherichia coli. Eur J Biochem. 1967 Jul;2(1):26–31. doi: 10.1111/j.1432-1033.1967.tb00100.x. [DOI] [PubMed] [Google Scholar]
  13. Koval S. F., Meadow P. M. The relationship between aminosugars in the lipopolysaccharide, serotype, and aeruginocin sensitivity in strains of Pseudomonas aeruginosa. J Gen Microbiol. 1975 Dec;91(2):437–440. doi: 10.1099/00221287-91-2-437. [DOI] [PubMed] [Google Scholar]
  14. Lee C. H., Schaffner C. P. Perimycin: chemistry of perosamine. Tetrahedron Lett. 1966 Nov;47:5837–5840. doi: 10.1016/s0040-4039(00)76093-x. [DOI] [PubMed] [Google Scholar]
  15. Levvy G. A., Hay A. J., Conchie J., Strachan I. The determination of the individual neutral and amino sugars in carbohydrates. Biochim Biophys Acta. 1970 Nov 24;222(2):333–338. doi: 10.1016/0304-4165(70)90121-2. [DOI] [PubMed] [Google Scholar]
  16. Liau D. F., Melly M. A., Hash J. H. Surface polysaccharide from Staphylococcus aureus M that contains taurine, D-aminogalacturonic acid, and D-fucosamine. J Bacteriol. 1974 Sep;119(3):913–922. doi: 10.1128/jb.119.3.913-922.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Liav A., Sharon N. Synthesis of 2,4-diacetamido-2,4,6-trideoxy-L-altrose, -L-idose, and -L-talose from benzyl 6-deoxy-3,4-O-isopropylidene-beta-L-galactopyranoside. Carbohydr Res. 1973 Sep;30(1):109–126. doi: 10.1016/s0008-6215(00)82178-3. [DOI] [PubMed] [Google Scholar]
  18. Niedermeier W. Gas chromatography of neutral and amino sugars in glycoproteins. Anal Biochem. 1971 Apr;40(2):465–475. doi: 10.1016/0003-2697(71)90407-6. [DOI] [PubMed] [Google Scholar]
  19. Omura S., Katagiri M., Atsumi K., Hata T., Jakubowski A. A., Springs E. B., Tishler M. Structure of prumycin. J Chem Soc Perkin 1. 1974;0(14):1627–1631. doi: 10.1039/p19740001627. [DOI] [PubMed] [Google Scholar]
  20. PARK J. T., JOHNSON M. J. A submicrodetermination of glucose. J Biol Chem. 1949 Nov;181(1):149–151. [PubMed] [Google Scholar]
  21. Partridge S. M. Filter-paper partition chromatography of sugars: 1. General description and application to the qualitative analysis of sugars in apple juice, egg white and foetal blood of sheep. with a note by R. G. Westall. Biochem J. 1948;42(2):238–250. doi: 10.1042/bj0420238. [DOI] [PMC free article] [PubMed] [Google Scholar]
  22. Paulsen H., Steinert K., Heyns K. Monosaccharide mit stickstoffhaltigem Ring, XXVI Darstellung freier 4-Amino-4-desoxy-D-glucose und 4-Amino-4-desoxy-D-galaktose. Dimerisierung zu Bis-Pyrrolidin-Zuckern. Chem Ber. 1970;103(5):1599–1620. doi: 10.1002/cber.19701030531. [DOI] [PubMed] [Google Scholar]
  23. Perry M. B., Webb C. Analysis of 2-amino-2-deoxyhexoses by gas-liquid partition chromatography. Can J Biochem. 1968 Sep;46(9):1163–1165. doi: 10.1139/o68-173. [DOI] [PubMed] [Google Scholar]
  24. 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]
  25. ROSEN H. A modified ninhydrin colorimetric analysis for amino acids. Arch Biochem Biophys. 1957 Mar;67(1):10–15. doi: 10.1016/0003-9861(57)90241-2. [DOI] [PubMed] [Google Scholar]
  26. Redmond J. W. 4-Amino-4,6-dideoxy-D-mannose (D-perosamine): a component of the lipopolysaccharide of Vibrio cholerae 569B (Inaba). FEBS Lett. 1975 Feb 1;50(2):147–149. doi: 10.1016/0014-5793(75)80476-5. [DOI] [PubMed] [Google Scholar]
  27. SHARON N., JEANLOZ R. W. The diaminohexose component of a polysaccharide isolated from Bacillus subtilis. J Biol Chem. 1960 Jan;235:1–5. [PubMed] [Google Scholar]
  28. 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]
  29. Sempere J. M., Gancedo C., Asensio C. Determination of galactosamine and N-acetylgalactosamine in the presence of other hexosamines with galactose oxidase. Anal Biochem. 1965 Sep;12(3):509–515. doi: 10.1016/0003-2697(65)90217-4. [DOI] [PubMed] [Google Scholar]
  30. Simmons D. A. The immunochemistry of Shigella flexneri O-antigens. The structure and biosynthesis of the O-specific side chains of some representative serotypes. Eur J Biochem. 1969 Dec;11(3):554–575. doi: 10.1111/j.1432-1033.1969.tb00808.x. [DOI] [PubMed] [Google Scholar]
  31. Snyder S. L., Sobocinski P. Z. An improved 2,4,6-trinitrobenzenesulfonic acid method for the determination of amines. Anal Biochem. 1975 Mar;64(1):284–288. doi: 10.1016/0003-2697(75)90431-5. [DOI] [PubMed] [Google Scholar]
  32. Suzuki N. Correlation between pyocin-sensitivity and 2-amino sugar composition of Pseudomonas aeruginosa. FEBS Lett. 1974 Nov 15;48(2):301–305. doi: 10.1016/0014-5793(74)80491-6. [DOI] [PubMed] [Google Scholar]
  33. Suzuki N. Isolation of DL-fucosamine from Pseudomonas aeruginosa N10. Biochim Biophys Acta. 1969 Apr 1;177(2):371–373. doi: 10.1016/0304-4165(69)90154-8. [DOI] [PubMed] [Google Scholar]
  34. 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]
  35. 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]
  36. WHEAT R. W., ROLLINS E. L., LEATHERWOOD J. M. Characterization of a 4-amino-4:6-dideoxy aldohexose from Chromobacterium violaceum. Biochem Biophys Res Commun. 1962 Sep 25;9:120–125. doi: 10.1016/0006-291x(62)90099-2. [DOI] [PubMed] [Google Scholar]
  37. Wilkinson S. G., Galbrath L. Studies of lipopolysaccharides from Pseudomonas aeruginosa. Eur J Biochem. 1975 Mar 17;52(2):331–343. doi: 10.1111/j.1432-1033.1975.tb04001.x. [DOI] [PubMed] [Google Scholar]
  38. 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]
  39. Yoshida A. Micromethod for the quantitative determination of L-alanine. Anal Biochem. 1965 May;11(2):383–386. doi: 10.1016/0003-2697(65)90028-x. [DOI] [PubMed] [Google Scholar]
  40. Zehavi U., Sharon N. Structural studies of 4-acetamido-2-amino-2,4,6-trideoxy-D-glucose (N-acetylbacillosamine), the N-acetyldiamino sugar of Bacillus licheniformis. J Biol Chem. 1973 Jan 25;248(2):433–438. [PubMed] [Google Scholar]

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