Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1981 Aug 1;197(2):293–299. doi: 10.1042/bj1970293

The release of N-acetyl- and N-glycolloyl-neuraminic acid from soluble complex carbohydrates and erythrocytes by bacterial, viral and mammalian sialidases.

A P Corfield, R W Veh, M Wember, J C Michalski, R Schauer
PMCID: PMC1163126  PMID: 7325957

Abstract

A series of substrates, sialyl(2 leads to 6)GalNAc and ganglioside GM3, containing either N-acetylneuraminic acid (AcNeu) or N-glycolloylneuraminic acid (GcNeu), has been prepared. The trisaccharide GcNeu(2 leads to 3)lactose was preapred by ozonolysis of GcNeu-GM3, and the disaccharides AcNeu(2 leads to 6)GalNAc and GcNeu(2 leads to 6)GalNAc were isolated from bovine submandibular-gland mucin by alkali elimination. Sialidases from Newcastle-disease virus, fowl-plague virus, influenza virus A2, Clostridium perfringens, Vibrio cholerae, Arthrobacter ureafaciens and human liver lysosomes were studied with the above substrates and all showed poorer cleavage of GcNeu-containing substrates when compared with the corresponding AcNeu-containing compounds. This was reflected in the Km and Vmax. values of these sialidases. Differences between viral and bacterial sialidases could be detected on the basis of their kinetic constants and time curves of sialic acid release. Preferred release of AcNeu relative to GcNeu was also observed with bovine submandibular gland mucin and a mixture of human and porcine erythrocytes, macromolecular substrates containing both AcNeu and GcNeu. The significance of differential cleavage of AcNeu and GcNeu by sialidases is considered together with examples of the role of GcNeu in physiologicaL systems.

Full text

PDF
293

Selected References

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

  1. Brossmer R., Nebelin E. Synthesis of N-formyl- and N-succinyl-D-neuraminic acid on the specificity of neuraminidase. FEBS Lett. 1969 Aug;4(4):335–336. doi: 10.1016/0014-5793(69)80269-3. [DOI] [PubMed] [Google Scholar]
  2. Codington J. F., Klein G., Silber C., Linsley K. B., Jeanloz R. W. Variations in the sialic acid compositions in glycoproteins of mouse ascites tumor cell surfaces. Biochemistry. 1979 May 29;18(11):2145–2149. doi: 10.1021/bi00578a002. [DOI] [PubMed] [Google Scholar]
  3. Den H., Malinzak D. A., Rosenberg A. Cytotoxic contaminants in commercial Clostridium perfringens neuraminidase preparations purified by affinity chromatography. J Chromatogr. 1975 Aug 20;111(1):217–222. doi: 10.1016/s0021-9673(01)80167-9. [DOI] [PubMed] [Google Scholar]
  4. Drzeniek R. Substrate specificity of neuraminidases. Histochem J. 1973 May;5(3):271–290. doi: 10.1007/BF01004994. [DOI] [PubMed] [Google Scholar]
  5. Faillard H., Ferreira do Amaral C., Blohm M. Untersuchungen zur enzymatischen Spezifität der Neuraminidase und N-Acyl-neuraminat-Lyase in bezug auf die N-Substitution. Hoppe Seylers Z Physiol Chem. 1969 Jul;350(7):798–802. [PubMed] [Google Scholar]
  6. Hakomori S., Saito T. Isolation and characterization of a glycosphingolipid having a new sialic acid. Biochemistry. 1969 Dec;8(12):5082–5088. doi: 10.1021/bi00840a061. [DOI] [PubMed] [Google Scholar]
  7. Higashi H., Naiki M., Matuo S., Okouchi K. Antigen of "serum sickness" type of heterophile antibodies in human sera: indentification as gangliosides with N-glycolylneuraminic acid. Biochem Biophys Res Commun. 1977 Nov 21;79(2):388–395. doi: 10.1016/0006-291x(77)90169-3. [DOI] [PubMed] [Google Scholar]
  8. Iwamori M., Nagai Y. GM3 ganglioside in various tissues of rabbit. Tissue-specific distribution of N-glycolylneuraminic acid-containing GM31. J Biochem. 1978 Dec;84(6):1609–1615. doi: 10.1093/oxfordjournals.jbchem.a132287. [DOI] [PubMed] [Google Scholar]
  9. JAMESON P., LEVINE A. S. SUBSTRATE SPECIFICITY OF NEUROTROPIC INFLUENZA VIRUS NEURAMINIDASES. J Bacteriol. 1965 Aug;90:563–564. doi: 10.1128/jb.90.2.563-564.1965. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Kamerling J. P., Gerwig G. J., Vliegenthart J. F., Clamp J. R. Characterization by gas-liquid chromatography-mass spectrometry and proton-magnetic-resonance spectroscopy of pertrimethylsilyl methyl glycosides obtained in the methanolysis of glycoproteins and glycopeptides. Biochem J. 1975 Dec;151(3):491–495. doi: 10.1042/bj1510491. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Nees S., Veh R. W., Schauer R. Purification and characterization of neuraminidase from Clostridium perfringens. Hoppe Seylers Z Physiol Chem. 1975 Jun;356(6):1027–1042. doi: 10.1515/bchm2.1975.356.s1.1027. [DOI] [PubMed] [Google Scholar]
  12. Ohman R., Hygstedt O. The isolation of sialyllactosides with the aid of gel filtration. Anal Biochem. 1968 Jun;23(3):391–402. doi: 10.1016/0003-2697(68)90230-3. [DOI] [PubMed] [Google Scholar]
  13. SVENNERHOLM L. CHROMATOGRAPHIC SEPARATION OF HUMAN BRAIN GANGLIOSIDES. J Neurochem. 1963 Sep;10:613–623. doi: 10.1111/j.1471-4159.1963.tb08933.x. [DOI] [PubMed] [Google Scholar]
  14. Schauer R. Characterization of sialic acids. Methods Enzymol. 1978;50:64–89. doi: 10.1016/0076-6879(78)50008-6. [DOI] [PubMed] [Google Scholar]
  15. Schauer R., Faillard H. Zur Wirkungsspezifität der Neuraminidase. Das Verhalten isomerer N.O-Diacetylneuraminsäureglykoside im Submaxillarismucin von Pferd und Rind bei Einwirkung bakterieller Neuraminidase. Hoppe Seylers Z Physiol Chem. 1968 Aug;349(8):961–968. [PubMed] [Google Scholar]
  16. Seyfried T. N., Ando S., Yu R. K. Isolation and characterization of human liver hematoside. J Lipid Res. 1978 Jul;19(5):538–543. [PubMed] [Google Scholar]
  17. Tettamanti G., Pigman W. Purification and characterization of bovine and ovine submaxillary mucins. Arch Biochem Biophys. 1968 Mar 20;124(1):41–50. doi: 10.1016/0003-9861(68)90301-9. [DOI] [PubMed] [Google Scholar]
  18. Uchida Y., Tsukada Y., Sugimori T. Distribution of neuraminidase in Arthrobacter and its purification by affinity chromatography. J Biochem. 1977 Nov;82(5):1425–1433. doi: 10.1093/oxfordjournals.jbchem.a131830. [DOI] [PubMed] [Google Scholar]
  19. WARREN L. The thiobarbituric acid assay of sialic acids. J Biol Chem. 1959 Aug;234(8):1971–1975. [PubMed] [Google Scholar]
  20. Wiegandt H., Bücking H. W. Carbohydrate components of extraneuronal gangliosides from bovine and human spleen, and bovine kidney. Eur J Biochem. 1970 Aug;15(2):287–292. doi: 10.1111/j.1432-1033.1970.tb01006.x. [DOI] [PubMed] [Google Scholar]
  21. Yasue S., Handa S., Miyagawa S., Inoue J., Hasegawa A., Yamakawa T. Difference in form of sialic acid in red blood cell glycolipids of different breeds of dogs. J Biochem. 1978 Apr;83(4):1101–1107. doi: 10.1093/oxfordjournals.jbchem.a131999. [DOI] [PubMed] [Google Scholar]
  22. van Halbeek H., Dorland L., Vliegenthart J. F., Fiat A. M., Jolles P. A 360-MHz 1H-NMR study of three oligosaccharides isolated from cow kappa-casein. Biochim Biophys Acta. 1980 Jun 26;623(2):295–300. doi: 10.1016/0005-2795(80)90257-3. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES