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. 1992 Oct 1;287(Pt 1):311–316. doi: 10.1042/bj2870311

Bovine colostrum CMP-NeuAc:Gal beta(1-->4)GlcNAc-R alpha(2-->6)-sialyltransferase is involved in the synthesis of the terminal NeuAc alpha(2-->6)GalNAc beta(1-->4)GlcNAc sequence occurring on N-linked glycans of bovine milk glycoproteins.

M Nemansky 1, D H Van den Eijnden 1
PMCID: PMC1133160  PMID: 1417784

Abstract

Bovine colostrum CMP-NeuAc:Gal beta(-->4)GlcNAc-R alpha(2-->6)-sialyltransferase (alpha 6-sialyltransferase) appears to be capable of catalysing alpha 6-sialylation of the disaccharide GalNAc beta(1-->4)GlcNAc to yield the trisaccharide NeuAc alpha(2-->6)GalNAc beta(1-->4)GlcNAc. This provides an enzymic basis for the occurrence of this sialylated structure on the N-linked glycans of a number of bovine milk glycoproteins. Competition experiments using Gal beta(1-->4)GlcNAc and GalNAc beta(-->4)GlcNAc as acceptors indicate that both substrates are recognized by a single active site on the alpha 6-sialyltransferase. Extrapolation of these results suggests that the NeuAc alpha(2-->6)GalNAc beta(1-->4)GlcNAc structural element occurring on the N-linked glycans of several human glycoproteins are similarly synthesized by the action of a Gal beta(1-->4)GlcNAc-R alpha(2-->6)-sialyltransferase.

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Selected References

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  1. Baenziger J. U., Green E. D. Pituitary glycoprotein hormone oligosaccharides: structure, synthesis and function of the asparagine-linked oligosaccharides on lutropin, follitropin and thyrotropin. Biochim Biophys Acta. 1988 Jun 9;947(2):287–306. doi: 10.1016/0304-4157(88)90012-3. [DOI] [PubMed] [Google Scholar]
  2. Bergh M. L., Koppen P. L., Van den Eijnden D. H. Specificity of ovine submaxillary-gland sialyltransferases. Application of high-pressure liquid chromatography in the identification of sialo-oligosaccharide products. Biochem J. 1982 Feb 1;201(2):411–415. doi: 10.1042/bj2010411. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Carlson D. M., McGuire E. J., Jourdian G. W., Roseman S. The sialic acids. XVI. Isolation of a mucin sialyltransferase from sheep submaxillary gland. J Biol Chem. 1973 Aug 25;248(16):5763–5773. [PubMed] [Google Scholar]
  4. Chan A. L., Morris H. R., Panico M., Etienne A. T., Rogers M. E., Gaffney P., Creighton-Kempsford L., Dell A. A novel sialylated N-acetylgalactosamine-containing oligosaccharide is the major complex-type structure present in Bowes melanoma tissue plasminogen activator. Glycobiology. 1991 Mar;1(2):173–185. doi: 10.1093/glycob/1.2.173. [DOI] [PubMed] [Google Scholar]
  5. Joziasse D. H., Schiphorst W. E., Van den Eijnden D. H., Van Kuik J. A., Van Halbeek H., Vliegenthart J. F. Branch specificity of bovine colostrum CMP-sialic acid: Gal beta 1----4GlcNAc-R alpha 2----6-sialyltransferase. Sialylation of bi-, tri-, and tetraantennary oligosaccharides and glycopeptides of the N-acetyllactosamine type. J Biol Chem. 1987 Feb 15;262(5):2025–2033. [PubMed] [Google Scholar]
  6. Joziasse D. H., Schiphorst W. E., van den Eijnden D. H., van Kuik J. A., van Halbeek H., Vliegenthart J. F. Branch specificity of bovine colostrum CMP-sialic acid: N-acetyllactosaminide alpha 2----6-sialyltransferase. Interaction with biantennary oligosaccharides and glycopeptides of N-glycosylproteins. J Biol Chem. 1985 Jan 25;260(2):714–719. [PubMed] [Google Scholar]
  7. Joziasse D. H., Shaper N. L., Kim D., Van den Eijnden D. H., Shaper J. H. Murine alpha 1,3-galactosyltransferase. A single gene locus specifies four isoforms of the enzyme by alternative splicing. J Biol Chem. 1992 Mar 15;267(8):5534–5541. [PubMed] [Google Scholar]
  8. Kato Y., Spiro R. G. Characterization of a thyroid sulfotransferase responsible for the 3-O-sulfation of terminal beta-D-galactosyl residues in N-linked carbohydrate units. J Biol Chem. 1989 Feb 25;264(6):3364–3371. [PubMed] [Google Scholar]
  9. Montreuil J. Primary structure of glycoprotein glycans: basis for the molecular biology of glycoproteins. Adv Carbohydr Chem Biochem. 1980;37:157–223. doi: 10.1016/s0065-2318(08)60021-9. [DOI] [PubMed] [Google Scholar]
  10. O'Hanlon T. P., Lau K. M., Wang X. C., Lau J. T. Tissue-specific expression of beta-galactoside alpha-2,6-sialyltransferase. Transcript heterogeneity predicts a divergent polypeptide. J Biol Chem. 1989 Oct 15;264(29):17389–17394. [PubMed] [Google Scholar]
  11. Paulson J. C., Beranek W. E., Hill R. L. Purification of a sialyltransferase from bovine colostrum by affinity chromatography on CDP-agarose. J Biol Chem. 1977 Apr 10;252(7):2356–2362. [PubMed] [Google Scholar]
  12. Paulson J. C., Rearick J. I., Hill R. L. Enzymatic properties of beta-D-galactoside alpha2 leads to 6 sialytransferase from bovine colostrum. J Biol Chem. 1977 Apr 10;252(7):2363–2371. [PubMed] [Google Scholar]
  13. Pfeiffer G., Dabrowski U., Dabrowski J., Stirm S., Strube K. H., Geyer R. Carbohydrate structure of a thrombin-like serine protease from Agkistrodon rhodostoma. Structure elucidation of oligosaccharides by methylation analysis, liquid secondary-ion mass spectrometry and proton magnetic resonance. Eur J Biochem. 1992 May 1;205(3):961–978. doi: 10.1111/j.1432-1033.1992.tb16863.x. [DOI] [PubMed] [Google Scholar]
  14. Rearick J. I., Sadler J. E., Paulson J. C., Hill R. L. Enzymatic characterization of beta D-galactoside alpha2 leads to 3 sialyltransferase from porcine submaxillary gland. J Biol Chem. 1979 Jun 10;254(11):4444–4451. [PubMed] [Google Scholar]
  15. Skelton T. P., Hooper L. V., Srivastava V., Hindsgaul O., Baenziger J. U. Characterization of a sulfotransferase responsible for the 4-O-sulfation of terminal beta-N-acetyl-D-galactosamine on asparagine-linked oligosaccharides of glycoprotein hormones. J Biol Chem. 1991 Sep 15;266(26):17142–17150. [PubMed] [Google Scholar]
  16. Spiro R. G., Bhoyroo V. D. Occurrence of sulfate in the asparagine-linked complex carbohydrate units of thyroglobulin. Identification and localization of galactose 3-sulfate and N-acetylglucosamine 6-sulfate residues in the human and calf proteins. J Biol Chem. 1988 Oct 5;263(28):14351–14358. [PubMed] [Google Scholar]
  17. Van den Eijnden D. H., Schiphorst W. E. Detection of beta-galactosyl(1 leads to 4)N-acetylglucosaminide alpha(2 leads to 3)-sialyltransferase activity in fetal calf liver and other tissues. J Biol Chem. 1981 Apr 10;256(7):3159–3162. [PubMed] [Google Scholar]
  18. Wang X., O'Hanlon T. P., Young R. F., Lau J. T. Rat beta-galactoside alpha 2,6-sialyltransferase genomic organization: alternate promoters direct the synthesis of liver and kidney transcripts. Glycobiology. 1990 Sep;1(1):25–31. doi: 10.1093/glycob/1.1.25. [DOI] [PubMed] [Google Scholar]
  19. Weinstein J., de Souza-e-Silva U., Paulson J. C. Sialylation of glycoprotein oligosaccharides N-linked to asparagine. Enzymatic characterization of a Gal beta 1 to 3(4)GlcNAc alpha 2 to 3 sialyltransferase and a Gal beta 1 to 4GlcNAc alpha 2 to 6 sialyltransferase from rat liver. J Biol Chem. 1982 Nov 25;257(22):13845–13853. [PubMed] [Google Scholar]
  20. Weisshaar G., Hiyama J., Renwick A. G., Nimtz M. NMR investigations of the N-linked oligosaccharides at individual glycosylation sites of human lutropin. Eur J Biochem. 1991 Jan 1;195(1):257–268. doi: 10.1111/j.1432-1033.1991.tb15702.x. [DOI] [PubMed] [Google Scholar]
  21. de Waard P., Koorevaar A., Kamerling J. P., Vliegenthart J. F. Structure determination by 1H NMR spectroscopy of (sulfated) sialylated N-linked carbohydrate chains released from porcine thyroglobulin by peptide-N4-(N-acetyl-beta-glucosaminyl)asparagine amidase-F. J Biol Chem. 1991 Mar 5;266(7):4237–4243. [PubMed] [Google Scholar]
  22. van den Eijnden D. H., Joziasse D. H., Dorland L., van Halbeek H., Vliegenthart J. F., Schmid K. Specificity in the enzymic transfer of sialic acid to the oligosaccharide branches of b1- and triantennary glycopeptides of alpha 1-acid glycoprotein. Biochem Biophys Res Commun. 1980 Feb 12;92(3):839–845. doi: 10.1016/0006-291x(80)90779-2. [DOI] [PubMed] [Google Scholar]
  23. van den Eijnden D. H., Koenderman A. H., Schiphorst W. E. Biosynthesis of blood group i-active polylactosaminoglycans. Partial purification and properties of an UDP-GlcNAc:N-acetyllactosaminide beta 1----3-N-acetylglucosaminyltransferase from Novikoff tumor cell ascites fluid. J Biol Chem. 1988 Sep 5;263(25):12461–12471. [PubMed] [Google Scholar]
  24. van den Eijnden D. H., van Dijk W. A convenient method for the preparation of cytidine 5'-monophospho-N-acetylneuraminic acid. Hoppe Seylers Z Physiol Chem. 1972 Dec;353(12):1817–1820. doi: 10.1515/bchm2.1972.353.2.1817. [DOI] [PubMed] [Google Scholar]

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