Enzymatic transfer of a β1,6-linked N-acetylglucosamine to the α-galactose of globo-N-tetraose: In vitro synthesis of a novel hybrid pentasaccharide of lacto-globo type

Glycobiology

Volumn 7, Issue 5, 1997, Pages 711-718

  Natunen, Jari ^a   Seppo, Antti ^a,c   Helin, Jari ^a,b   Reinhold, Bruce B ^b   Räbinä, Jarkko ^a   Costello, Catherine E ^b   Renkonen, Ossi ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

ESI CID mass spectrometry; Hog gastric; Hybrid glycan; IP antigen; N acetylglucosaminyltransferase

Indexed keywords

ANTIGEN; PENTASACCHARIDE; GLOBOSIDE; GLOBOTETRAOSE; N ACETYLGLUCOSAMINYLTRANSFERASE; OLIGOSACCHARIDE; TRITIUM; UDP GLCNAC GB(5)CER BETA1 6N ACETYLGLUCOSAMINYLTRANSFERASE; UDP-GLCNAC-GB(5)CER BETA1-6N-ACETYLGLUCOSAMINYLTRANSFERASE; URIDINE DIPHOSPHATE N ACETYLGLUCOSAMINE;

ANIMAL TISSUE; ARTICLE; CARBOHYDRATE SYNTHESIS; CELL ADHESION; CHROMATOGRAPHY; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SPECIFICITY; IN VITRO STUDY; ISOTOPE LABELING; MASS SPECTROMETRY; MICROSOME; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STOMACH MUCOSA; SWINE; ANIMAL; CARBOHYDRATE ANALYSIS; CATTLE; CHEMISTRY; CONFORMATION; ENZYMOLOGY; EPITHELIUM; METABOLISM; MILK; MOLECULAR GENETICS; SYNTHESIS; TRACHEA;

ANIMALIA; BOVINAE; SUS SCROFA;

ANIMALS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CATTLE; EPITHELIUM; GASTRIC MUCOSA; GLOBOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES; MILK; MOLECULAR SEQUENCE DATA; N-ACETYLGLUCOSAMINYLTRANSFERASES; OLIGOSACCHARIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SUBSTRATE SPECIFICITY; SWINE; TRACHEA; TRITIUM; URIDINE DIPHOSPHATE N-ACETYLGLUCOSAMINE;

EID: 0030610560     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/7.5.711     Document Type: Article

References (44)

1. Bierhuizen, M.F.A. and Fukuda, M. (1992) Expression cloning of a cDNA encoding UDP-GlcNAc:Galβ1-3GalNAc-R (GlcNAc to GalNAc) β1-6GlcNAc transferase by gene transfer into CHO cells expressing polyoma large tumor antigen. Proc. Natl. Acad. Sci. USA, 89, 9326-9330.
2. Bierhuizen, M.F.A., Maemura, K., Kudo, S. and Fukuda, M. (1995) Genomic organization of core 2 and I branching β-1,6-N-acetylglucosaminyltransferases. Implication for evolution of the β-1,6-N-acetylglucosaminyltransferase gene family. Glycobiology, 5, 417-425.
3. Bouchon, B., Levery, S.B., Clausen, H. and Hakomori, S.-I. (1992) Production and characterization of a monoclonal antibody (BBH5) directed to ganglioside lactone. Glycoconjugate J., 9, 27-38.
4. Brew, K., Vanaman, T.C. and Hill, R.L. (1968) The role of α-lactalbumin and the a protein lactose synthetase: a unique mechanism for the control of a biological reaction. Proc. Natl. Acad. Sci. USA. 59, 491-497.
5. Brockhausen, I., Williams, D., Matta, K.L., Orr, J. and Schachter, H. (1983) Mucin synthesis. III. UDP-GlcNAc:Galβ1-3(GlcNAcβ1-6)GalNAc-R (GlcNAc to Gal) β3-N-acetylglucosaminyltransferase, an enzyme in porcine gastric mucosa involved in the elongation of mucin-type oligosaccharides. Can. J. Biochem. Cell Biol., 61, 1322-1333.
6. 2 by a β6-N-acetylglucosaminyltransferase in pig gastric mucosa. Eur. J. Biochem., 157, 463-174.
7. Ciucanu, I. and Kerek, F. (1984) A simple and rapid method for the permethylation of carbohydrates. Carbohydr. Res., 131, 209-217.
8. DeGasperi, R., Koerner, T.A.W., Quarles, R.H., Ilyas, A.A., Ishikawa, Y., Li, S.-C. and Li, Y.-T. (1987) Isolation and characterization of gangliosides with hybrid neolacto-ganglio-type sugar chains. J. Biol. Chem., 262, 17149-17155.
9. 3-ganglioside. Glycoconjugate J., 9, 303-306.
10. Domon, B. and Costello, C.E. (1988) A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J., 5, 397-409.
11. Gillard, B.K., Jones, M.A., Turner, A.A., Lewis, D.E. and Marcus, D.M. (1990) Interferon-γ alters expression of endothelial cell-surface glycosphingolipids. Arch. Biochem. Biophys., 279, 122-129.
12. Gu, J., Nishikawa, A., Fujii, S., Gasa, S. and Taniguchi, N. (1992) Biosynthesis of blood group I and i antigens in rat tissues. Identification of a novel β1-6-N-acetylglucosaminyltransferase. J. Biol. Chem., 267, 2994-2999.
13. Hakomori, S. (1981) Glycosphingolipids in cellular interaction, differentiation, and oncogenesis. Annu. Rev. Biochem., 50, 733-64.
14. Kannagi, R., Levery, S.B. and Hakori, S. (1983) Sequential change of carbohydrate antigen associated with differentiation of murine leukemia cells: i-I antigenic conversion and shifting of glycolipid synthesis. Proc. Natl. Acad. Sci. USA, 80, 2844-2848.
15. Kannagi, R., Levery, S.B. and Hakomori, S. (1984) Hybrid type glycolipids (lacto-ganglio series) with a novel branched structure. J. Biol. Chem., 259, 8444-8451.
16. Kijimoto-Ochiai, S., Tashiro, A., Katagiri, Y.U., Hatae, T., Kobayashi, S. and Okuyama, H. (1990) Forssman antigen expressed on lymph node cells of MRL/MpJ-lpr/lpr mice is of a glycoprotein nature. Microbiol. Immunol., 34, 299-309.
17. Koenderman, A.H.L., Koppen, P.L. and van den Eijnden, D.H. (1987) Biosynthesis of polylactosaminoglycans. Novikoff ascites tumor cells contain two UDP-GlcNAc:β-galactoside β1-6-N-acetylglucosaminyltransferase activities. Eur. J. Biochem., 166, 199-208.
18. Lanne, B., Olsson, B.-M., Jovall, P.-Å., Ångstrom, J., Linder, H., Marklund, B.-I., Bergström, J. and Karlsson, K.-A. (1995) Glycoconjugate receptors for P-fimbriated Escherichia coli in the mouse. J. Biol. Chem., 270, 9017-9025.
19. Larson, G. (1986) Globoseries glycosphingolipids of human meconium. Arch. Biochem. Biophys., 246, 531-545.
20. Leppanen, A., Penttilä, L., Niemelä, R., Helin, J., Seppo, A., Lusa, S. and Renkonen, O. (1991) Human serum contains a novel β1-6-N-acetylglucosaminyltransferase activity that is involved in midchain branching of oligo(N-acetyllactosaminoglycans). Biochemistry, 30, 9287-9296.
21. Linsley, K.B., Chan, S.-Y., Chan, S., Reinhold, B.B., Lisi, P.J. and Reinhold, V.N. (1994) Applications of electrospray mass spectrometry to erythropoietin N-and O-linked glycans. Anal. Biochem., 219, 207-217.
22. Maaheimo, H., Renkonen, R., Turunen, J.P., Penttilä, L. and Renkonen, O. (1995) Synthesis of a divalent sialyl Lewis x O-glycan, a potent inhibitor of lymphocyte-endothelium adhesion. Evidence that multivalency enhances the saccharide binding to L-selectin. Eur. J. Biochem., 234, 616-625.
23. Marcus, D.M., Kundu, S.K. and Suzuki, A. (1981) The P blood group system: recent progress in immunochemistry and genetics. Semin. Hematol., 18, 63-71.
24. 1 glycosphingolipid. Biochemistry, 14, 4831-4837.
25. Natsuka, S. and Lowe, J.B. (1994) Enzymes involved in mammalian oligosaccharide biosynthesis. Curr. Opin. Struct. Biol., 4, 683-691.
26. Nilsson, U., Ray, A.K. and Magnusson, G. (1994) Synthesis of the globotetraose tetrasaccharide and terminal tri- and disaccharide fragments. Carbohydr. Res., 252, 117-136.
27. Osanai, T., Feizi, T., Chai, W., Lawson, A.M., Gustavsson, M.L., Sudo, K., Araki, M. and Yuen, C.-T. (1996) Two families of murine carbohydrate ligands for E-selectin. Biochem. Biophys. Res. Commun., 218, 610-615.
28. Ostrander, G.K., Levery, S.B., Eaton, H.L., Salyan, M.E.K., Hakomori, S. and Holmes, E.H. (1988) Isolation and characterization of four major neutral glycosphingolipids from the liver of the english sole (Parophyrus vetulus). J. Biol. Chem., 263, 18716-18725.
29. Filler, F., Cartron, J.-P., Maranduba, A., Veyrieres, A., Leroy, Y. and Fournet, B. (1984) Biosynthesis of blood group I antigens. Identification of a UDP-GlcNAc:GlcNAcβ1-3Gal(-R)β1-6(GlcNAc to Gal) N-acetylglucosaminyltransferase in hog gasric mucosa. J. Biol. Chem., 259, 13385-13390.
30. Poppe, L., Von der Lieth, C.-W. and Dabrowski, J. (1990) Conformation of the glycolipid globoside head group in various solvents and in the micellebound state. J. Am. Chem. Soc., 112, 7762-7771.
31. TP. Transfusion, 34, 427-431.
32. Reinhold, V.N., Reinhold, B.B. and Costello, C.E. (1995) Carbohydrate molecular weight profiling, sequence, linkage, and branching data: ES-MS and CID. Anal. Chem., 62, 1772-1784.
33. Renkonen, O., Penttilä, L., Makkonen, A., Niemelä, R., Leppänen, A., Helin, J. and Vainio, A. (1989) The linear tetrasaccharide, Galβ1-4GlcNAcβ1-6Galβ1-4GlcNAc, isolated from radiolabeled teratocarcinoma poly-N-acetyllactosaminoglycan resists the action of E.freundii endo-β-galactosidase. Glycoconjugate J., 6, 129-140.
34. Ropp, P., Little, M.R. and Cheng, P.-W. (1991) Mucin biosynthesis: Purification and characterization of a mucin β6N-acetylglucosaminyltransferase. J. Biol. Chem., 266, 23863-23871.
35. 4Cer β-1,6-GlcNAc transferase from mouse kidney. J. Biol. Chem., 269, 31143-31148.
36. Seko, A., Kitajima, K., Iwasaki, M., Inoue, S. and Inoue, Y. (1989) Structural studies of fertilization -associated carbohydrate-rich glycoproteins (Hyosophorin) isolated from the fertilized an unfertilized eggs of flounder, Paralichthys olivaceus. J. Biol. Chem., 264, 15922-15929.
37. Seppo, A., Penttilä, L., Makkonen, A., Leppänen, A., Niemelä, R., Jäntti, J., Helin, J. and Renkonen, O. (1990) Wheat germ agglutinin chromatography of GlcNAcβ1-3(GlcNAcβ1-6)Gal and GlcNAcβ1-3(GlcNAcβ1-6)Galβ1-4GlcNAc, obtained by in vitro synthesis and by partial cleavage of teratocarcinoma poly-N-acetyllactosaminoglycans. Biochem. Cell Biol., 68, 44-53.
38. Seppo, A., Penttilä, L., Niemelä, R., Maaheimo, H., Renkonen, O. and Keane, A. (1995) Enzymatic synthesis of octadecameric saccharides of multiply branched blood group I-type, carrying four distal α1,3-galactose or β1,3-GlcNAc residues. Biochemistry, 34, 4655-4661.
39. Shevinsky, L.H., Knowles, B.B., Damjanov, I. and Solter, T. (1982) Monoclonal antibody to murine embryos defines a stage-specific embryonic antigen expressed on mouse embryos and human teratocarcinoma cells. Cell, 30, 697-705.
40. Shigeta, K., Ito, Y., Ogawa, T., Kirihata, Y., Hakomori, S. and Kannagi, R. (1987) Monoclonal antibodies directed to chemically synthesized lactogangliotetraosylceramide, a leukemia-associated antigen having a novel branching structure. J. Biol. Chem., 262, 1358-1362.
41. Slomiany, B.L., Banas-Gruszka, Z., Zdebska, E. and Slomiany, A. (1982) Characterization of the Forssman active oligosaccharides from dog gastric mucus glycoprotein isolated with the use of a monoclonal antibody. J. Biol. Chem., 257, 9561-9565.
42. Tonegawa, Y. and Hakomori, S. (1977) "Ganglioprotein and globoprotein": the glycoproteins reacting with anti-ganglioside and anti-globoside antibodies and the ganglioprotein change associated with transformation. Biochem. Biophys. Res. Commun., 76, 9-17.
43. Whitfield, D.M., Pang, H., Carver, J.P. and Krepinsky, J.J. (1990) Synthesis of model oligosaccharides of biological significance. X. Synthesis and NMR and mass spectral analysis of trideuteriomethyl di-3,6-O-(4-O-β-D-galactopyranosyl-2-acetamido-2-deoxy-β-D- glucopyranosyl)-β-D-galactopyranoside: the I antigen branchpoint penta- and tetrasaccharides and a related trisaccharide. Can. J. Chem., 68, 942-952.
44. Yamamoto, F., Clausen, H., White, T., Marken, J. and Hakomori, S. (1990) Molecular genetic basis of the histo-blood group ABO system. Nature, 345, 229-233.