Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1978 Jun 1;171(3):549–557. doi: 10.1042/bj1710549

Isolation and structural characterization of alkali-labile oligosaccharides from bovine milk-fat-globule membrane.

G H Farrar, R Harrison
PMCID: PMC1183999  PMID: 580891

Abstract

Treatment of sialoglycopeptides derived from bovine milk-fat-globule membrane with alkaline borohydride released a reduced oligosaccharide fraction from which a tetrasaccharide and two trisaccharides were isolated. Periodate-oxidation studies coupled with methylation analysis and g.l.c.-mass spectrometry established their structures as: N-acetylneuraminyl-(2 leads to 3)-beta-D-galactopyranosyl-(1 leads to 3)-[N-acetylneuraminyl-(2 leads to 6)]-N-acetyl-D-galactosaminitol, N-acetylneuraminyl-(2 leads to 3)-D-glactopyranosyl-(1 leads to 3)-N-acetyl-D-galactosaminitol and beta-D-galactopyranosyl-(1 leads to 3)-[N-acteylneuraminyl-(2 leads to 6)]-N-acetyl-D-galactosaminitol respectively.

Full text

PDF
549

Selected References

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

  1. AMINOFF D. Methods for the quantitative estimation of N-acetylneuraminic acid and their application to hydrolysates of sialomucoids. Biochem J. 1961 Nov;81:384–392. doi: 10.1042/bj0810384. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Cuatrecasas P. Interaction of concanavalin A and wheat germ agglutinin with the insulin receptor of fat cells and liver. J Biol Chem. 1973 May 25;248(10):3528–3534. [PubMed] [Google Scholar]
  3. 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]
  4. Finne J. Structure of the O-glycosidically linked carbohydrate units of rat brain glycoproteins. Biochim Biophys Acta. 1975 Dec 15;412(2):317–325. doi: 10.1016/0005-2795(75)90046-x. [DOI] [PubMed] [Google Scholar]
  5. Glöckner W. M., Newman R. A., Dahr W., Uhlenbruck G. Alkali-labile oligosaccharides from glycoproteins of different erythrocyte and milk fat globule membranes. Biochim Biophys Acta. 1976 Sep 7;443(3):402–413. doi: 10.1016/0005-2736(76)90460-0. [DOI] [PubMed] [Google Scholar]
  6. 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]
  7. Harrison R., Higginbotham J. D., Newman R. Sialoglycopeptides from bovine milk fat globule membrane. Biochim Biophys Acta. 1975 May 21;389(3):449–463. doi: 10.1016/0005-2736(75)90156-x. [DOI] [PubMed] [Google Scholar]
  8. KLENK E., HENDRICKS U. W., GIELEN W. [beta-D-Galactosido-(1-3)-N-acetyl-D-galactosamine, a crystallized disaccharide from human brain gangliosides]. Hoppe Seylers Z Physiol Chem. 1962 Dec 15;330:140–144. doi: 10.1515/bchm2.1962.330.1.140. [DOI] [PubMed] [Google Scholar]
  9. Lisowska E., Duk M. Modification of amino groups of human-erythrocyte glycoproteins and the new concept on the structural basis of M and M blood-group specificity. Eur J Biochem. 1975 Jun;54(2):469–474. doi: 10.1111/j.1432-1033.1975.tb04158.x. [DOI] [PubMed] [Google Scholar]
  10. Newman R. A., Harrison R. Characterisation of the surface of bovine milk fat globule membrane using microelectrophoresis. Biochim Biophys Acta. 1973 Apr 16;298(4):798–809. doi: 10.1016/0005-2736(73)90384-2. [DOI] [PubMed] [Google Scholar]
  11. Newman R. A., Uhlenbruck G. G. Investigation into the occurrence and structure of lectin receptors on human and bovine erythrocytes milk fat globule and lymphocyte plasma-membrane glycoproteins. Eur J Biochem. 1977 Jun 1;76(1):149–155. doi: 10.1111/j.1432-1033.1977.tb11580.x. [DOI] [PubMed] [Google Scholar]
  12. Patton S., Keenan T. W. The milk fat globule membrane. Biochim Biophys Acta. 1975 Oct 31;415(3):273–309. doi: 10.1016/0304-4157(75)90011-8. [DOI] [PubMed] [Google Scholar]
  13. Powell J. T., Järlfors U., Brew K. Enzymic characteristics of fat globule membranes from bovine colostrum and bovine milk. J Cell Biol. 1977 Mar;72(3):617–627. doi: 10.1083/jcb.72.3.617. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Roseman S. The synthesis of complex carbohydrates by multiglycosyltransferase systems and their potential function in intercellular adhesion. Chem Phys Lipids. 1970 Oct;5(1):270–297. doi: 10.1016/0009-3084(70)90024-1. [DOI] [PubMed] [Google Scholar]
  15. Spiro R. G., Bhoyroo V. D. Structure of the O-glycosidically linked carbohydrate units of fetuin. J Biol Chem. 1974 Sep 25;249(18):5704–5717. [PubMed] [Google Scholar]
  16. Springer G. F., Desai P. R. Human blood-group MN and precursor specificities: structural and biological aspects. Carbohydr Res. 1975 Mar;40(1):183–192. doi: 10.1016/s0008-6215(00)82680-4. [DOI] [PubMed] [Google Scholar]
  17. Thomas D. B., Winzler R. J. Structural studies on human erythrocyte glycoproteins. Alkali-labile oligosaccharides. J Biol Chem. 1969 Nov 10;244(21):5943–5946. [PubMed] [Google Scholar]
  18. Thomas D. B., Winzler R. J. Structure of glycoproteins of human erythrocytes. Alkali-stable oligosaccharides. Biochem J. 1971 Aug;124(1):55–59. doi: 10.1042/bj1240055. [DOI] [PMC free article] [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. Woodruff J. J., Gesner B. M. The effect of neuraminidase on the fate of transfused lymphocytes. J Exp Med. 1969 Mar 1;129(3):551–567. doi: 10.1084/jem.129.3.551. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Yu R. K., Ledeen R. W. Gas--liquid chromatographic assay of lipid-bound sialic acids: measurement of gangliosides in brain of several species. J Lipid Res. 1970 Nov;11(6):506–516. [PubMed] [Google Scholar]
  22. Yu R. K., Ledeen R. Configuration of the ketosidic bond of sialic acid. J Biol Chem. 1969 Mar 10;244(5):1306–1313. [PubMed] [Google Scholar]

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

RESOURCES