Skip to main content
PMC home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1961 Dec;82(6):838–848. doi: 10.1128/jb.82.6.838-848.1961

SIALIC ACIDS (N,7-O-DIACETYLNEURAMINIC ACID AND N-ACETYLNEURAMINIC ACID) IN ESCHERICHIA COLI I.

Isolation and Identification

Charles W Dewitt a,1, Janet A Rowe a,2
PMCID: PMC279266  PMID: 13885921

Abstract

DeWitt, Charles W. (The Upjohn Co., Kalamazoo, Mich.) and Janet A. Rowe. Sialic acids (N,7-O-diacetylneuraminic acid and N-acetylneuraminic acid) in Escherichia coli. I. Isolation and identification. J. Bacteriol. 82:838–848. 1961.—Two sialic acids, N-acetylneuraminic acid and N,7-O-diacetylneuraminic acid, were obtained in crude mixtures from whole cells of Escherichia coli and from its endotoxin by weak acid hydrolysis followed by anion exchange resin chromatography. Yields from whole cells were 0.1 to 0.2% (dry weight) with 50 to 60% purity. Identification of the sialic acids was by comparative paper chromatography and colorimetric assays using the acidic p-dimethylaminobenzaldehyde (direct Ehrlich), resorcinol and thiobarbituric acid reactions. The N-acetyl derivative was also shown to be susceptible to hydrolysis by clostridial N-acetylneuraminic aldolase and the end products identified, N-acetylamannosamine by paper chromatography and pyruvic acid by oxidation of DPNH with lactic acid dehydrogenase. The two sialic acids were separated on paper chromatograms, eluted, and assays for total and ester acyl groups showed the suspected N-acetyl derivative to contain 0.11 O-acyl and 1.16 N-acetyl groups per mole sialic acid and the diacetyl derivative to have 1.10 O-acyl and 0.93 N-acetyl groups per mole. The O-acyl group was identified as acetyl by preparation of the hydroxamate.

Full text

PDF

Selected References

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

  1. AARONSON S., LESSIE T. Nonulosaminic acid (sialic acid) in protists. Nature. 1960 May 28;186:719–719. doi: 10.1038/186719a0. [DOI] [PubMed] [Google Scholar]
  2. BARRY G. T. Colominic acid, a polymer of N-acetylneuraminic acid. J Exp Med. 1958 Apr 1;107(4):507–521. doi: 10.1084/jem.107.4.507. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. BARRY G. T., GOEBEL W. F. Colominic acid, a substance of bacterial origin related to sialic acid. Nature. 1957 Jan 26;179(4552):206–206. doi: 10.1038/179206a0. [DOI] [PubMed] [Google Scholar]
  4. BARRY G. T., TSAI T. H., CHEN F. P. Chemical and serological relationships of certain bacterial polysaccharides containing sialic acid. Nature. 1960 Feb 27;185:597–598. doi: 10.1038/185597a0. [DOI] [PubMed] [Google Scholar]
  5. CARDINI C. E., LELOIR L. F. Enzymatic formation of acetylgalactosamine. J Biol Chem. 1957 Mar;225(1):317–324. [PubMed] [Google Scholar]
  6. CASTELLANI A. A., FERRI G., BOLOGNANI L., GRAZIANO V. Presence of sialic acid in connective tissue. Nature. 1960 Jan 2;185:36–37. doi: 10.1038/185037a0. [DOI] [PubMed] [Google Scholar]
  7. COMB D. G., ROSEMAN S. The sialic acids. I. The structure and enzymatic synthesis of N-acetylneuraminic acid. J Biol Chem. 1960 Sep;235:2529–2537. [PubMed] [Google Scholar]
  8. CORNFORTH J. W., FIRTH M. E., GOTTSCHALK A. The synthesis of N-acetylneuraminic acid. Biochem J. 1958 Jan;68(1):57–61. doi: 10.1042/bj0680057. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. DE WITT C. W., ROWE J. A. N,O-Diacetylneuraminic acid and N-acetylneuraminic acid in Escherichia coli. Nature. 1959 Aug 1;184(Suppl 6):381–382. doi: 10.1038/184381b0. [DOI] [PubMed] [Google Scholar]
  10. DEWITT C. W., ZELL E. A. Sialic acids (N,7-O-diacetylneuraminic acid and N-acetylneuraminic adcid) in Escherichia coli. II. Their presence on the cell wall surface and relationship to K antigen. J Bacteriol. 1961 Dec;82:849–856. doi: 10.1128/jb.82.6.849-856.1961. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. DUFF R. B., FARMER V. C. Identification of 6-O-acetyl-D-glucopyranose in Bacillus megaterium cultures; synthesis of 6-O-acetyl-D-glucopyranose and 6-O-acetyl-D-galactopyranose. Biochem J. 1958 Nov;70(3):515–520. doi: 10.1042/bj0700515. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. KLENK E., UHLENBRUCK G. Uber die Abspaltung von N-Glykolyl-neuraminsäure (P-Sialinsäure) aus dem Schweine-Submaxillaris-mucin durch das Receptor Destroying Enzyme. Hoppe Seylers Z Physiol Chem. 1957;307(2-6):266–271. [PubMed] [Google Scholar]
  13. LUDOWIEG J., DORFMAN A. A micromethod for the colorimetric determination of N-acetyl groups in acid mucopolysaccharides. Biochim Biophys Acta. 1960 Feb 26;38:212–218. doi: 10.1016/0006-3002(60)91233-6. [DOI] [PubMed] [Google Scholar]
  14. O'BRIEN P. J., ZILLIKEN F. Nucleotide-linked polyneuraminic acid peptides from Escherichia coli. Biochim Biophys Acta. 1959 Feb;31(2):543–545. doi: 10.1016/0006-3002(59)90032-0. [DOI] [PubMed] [Google Scholar]
  15. SCHRAMM G., MOHR E. Purification of neuraminidase from Vibrio cholerae. Nature. 1959 Jun 13;183(4676):1677–1678. doi: 10.1038/1831677a0. [DOI] [PubMed] [Google Scholar]
  16. STADTMAN E. R., BARKER H. A. Fatty acid synthesis by enzyme preparations of Clostridium kluyveri. VI. Reactions of acyl phosphates. J Biol Chem. 1950 Jun;184(2):769–793. [PubMed] [Google Scholar]
  17. SVENNERHOLM E., SVENNERHOLM L. Quantitative paper partition chromatography of sialic acids. Nature. 1958 Apr 19;181(4616):1154–1155. doi: 10.1038/1811154a0. [DOI] [PubMed] [Google Scholar]
  18. WARREN L. The thiobarbituric acid assay of sialic acids. J Biol Chem. 1959 Aug;234(8):1971–1975. [PubMed] [Google Scholar]
  19. WATSON R. G., MARINETTI G. V., SCHERP H. W. The specific hapten of group C (group II alpha) meningococcus. II. Chemical nature. J Immunol. 1958 Oct;81(4):337–344. [PubMed] [Google Scholar]
  20. ZILLIKEN F., WHITEHOUSE M. W. The nonulosaminic acids; neuraminic acids and related compounds (sialic acids). Adv Carbohydr Chem. 1958;13:237–263. [PubMed] [Google Scholar]

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

RESOURCES