Proton NMR study of triantennary complex type N-linked glycan chains: Assignment of proton chemical shifts of the β-Man residue in a basic unit of the triantennary glycan chain having a GlcNAcβ1→6Manα1→6Manβ→ sequence

Glycobiology

Volumn 7, Issue 1, 1997, Pages 31-36

  Taguchi, Tomohiko ^a   Muto, Yutaka ^a   Kitajima, Ken ^a   Yokoyama, Shigeyuki ^a   Inoue, Sadako ^b   Inoue, Yasuo ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

2D 1H NMR; Conformation of N Iinked glycan; GlcNAc transferase V; Triantennary N linked glycan

Indexed keywords

GLYCAN;

ARTICLE; CARBOHYDRATE ANALYSIS; IN VITRO STUDY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ACETYLGLUCOSAMINE; ANIMALS; CARBOHYDRATE SEQUENCE; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSE; MOLECULAR SEQUENCE DATA; POLYSACCHARIDES; PROTONS; TROUT;

EID: 0031058031     PISSN: 09596658     EISSN: None     Source Type: Journal    
DOI: 10.1093/glycob/7.1.31     Document Type: Article

References (51)

1. Bax, A. and Davis, D.G. (1985) MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson., 65, 355-360.
2. Bax, A. and Drobny, G.P. (1985) Optimization of two-dimensional homonuclear relayed coherence transfer NMR spectroscopy. J. Magn. Reson., 61, 306-320.
3. Berman, E. (1987) Conformational analysis and the fine structure of cross peaks in phase-sensitive homonuclear two-dimensional correlated NMR spectra of oligosaccharides. Eur. J. Biochem., 165, 385-391.
4. 13C-N.M.R. (125 MHz) study of N-linked glycopeptides derived from calf fetuin. Carbohydr. Res., 176, 1-15.
5. 1H-NMR spectroscopy. J. Carbohydr. Chem., 13, 513-543.
6. Bock, K., Arnarp, J. and Löngren, J. (1982) The preferred conformation of oligosaccharides derived from the complex-type carbohydrate portions of glycoproteins. Eur J. Biochem., 129, 171-178.
7. Bock, K., Duus, J.Ø., Hindsgaul, O. and Lindh, I. (1992) Analysis of conformationally restricted models for the (1→6)-branch of asparagine-linked oligosaccharides by n.m.r.-spectroscopy and HSEA calculation. Carbohydr. Res., 228, 1-20.
8. Bouwstra, J.B., Spoelstra, E.C., de Waard, P., Leeflang, B.R., Kamerling, J.P. and Vliegenthart, J.F.G. (1990) Conformational studies on the N-linked carbohydrate chain ot bromelain. Eur. J. Biochem., 190, 113-122.
9. Braunschweiler, L. and Ernst, R.R. (1983) Coherence transfer by isotropic mixing: application to proton correlation spectroscopy. J. Magn. Reson., 53, 521-528.
10. Brisson, J.-R. and Carver, J.P. (1983a) Solution conformation of αD(1-3)-and αD(1-6)-linked oligomannosides using proton nuclear magnetic resonance. Biochemistry, 22, 1362-1368.
11. Brisson, J.-R. and Carver, J.P. (1983b) Solution conformation of asparagine-linked oligosaccharides: α(1-2)-, α(1-3), β(1-2)-, and β(1-4)-linked units. Biochemistry, 22, 3671-3680.
12. Brisson, J.-R. and Carver, J.P. (1983c) Solution conformation of asparagine-linked oligosaccharides: α(1-6)-linked moiety. Biochemistry, 22, 3680-3686.
13. Cumming, D.A. and Carver, J.P. (1987a) Virtual and solution conformations of oligosaccharides. Biochemistry, 26, 6664-6676.
14. Cumming, D.A. and Carver, J.P. (1987b) Reevaluation of rotamer populations for 1,6 linkages: reconciliation with potential energy calculations. Biochemistry, 26, 6676-6683.
15. Cumming, D.A., Dime, D.S., Grey, A.A., Krepinsky, J.J. and Carver, J.P. (1986) Specific deuteration of a trimannoside confirms the existence of a disputed interresidue nuclear Overhauser enhancement. J. Biol. Chem., 261, 3208-3213.
16. Cumming, D.A., Shah, R.N., Krepinsky, J.J., Grey, A.A. and Carver, J.P. (1987) Solution conformation of the branch points of N-linked glycans: synthetic model compounds for tri-antennary and tetraantennary glycans. Biochemistry, 26, 6655-6663.
17. 1H-NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy. J. Am. Chem. Soc., 107, 2820-2821.
18. 1H NMR studies on an Asn-linked glycopeptide. J. Biol. Chem., 269, 3331-3338.
19. Dennis, J.W., Laferté, S., Waghorne, C., Breitman, M. and Kerbel, R.S. (1987) β1-6 Branching of Asn-linked oligosaccharides is directly associated with metastasis. Science, 236, 582-585.
20. Dennis, J.W. and Laferté, S. (1989) Oncodevelopmental expression of -GlcNAcβ1→6Manα1→6Manβ1-branched asparagine-linked oligosaccharides in murine tissues and human breast carcinomas. Cancer Res., 49, 945-950.
21. de Waard, P., Leeflang, B.R., Vliegenthart, J.F.G., Boelens, R., Vuister, G.W. and Kaptein, R. (1992) Application of 2D and 3D NMR experiments to the conformational study of a diantennary oligosaccharide. J. Biomol. NMR, 2, 211-226.
22. Fukuda, M. (1994) Cell surface carbohydrates: cell-type specific expression. In Fukuda, M., Hindsgaul, O. (eds), Molecular Glycobiology. IRL Press, Oxford, pp. 1-52.
23. Hokke, C.H., Bergwerff, A.A., van Dedem, G.W.K., Kamerling, J.P. and Vliegenthart, J.F.G. (1995) Structural analysis of the sialylated N-and O-linked carbohydrate chains of recombinant human erythropoietin expressed in Chinese hamster ovary cells. Sialylation patterns and branch location of dimeric N-acetyllactosamine units. Eur. J. Biochem., 228, 981-1088.
24. Homans, S.W. (1990) A molecular mechanical force field for the conformational analysis of oligosaccharides: comparison of theoretical and crystal structures of Manα1-3Manβ1-4GlcNAc. Biochemistry, 29, 9110-9118.
25. 1H NMR nuclear Overhauser effect measurements. FEBS Lett., 150, 503-506.
26. Homans, S.W., Dwek, R.A., Fernandes, D.L. and Rademacher, T.W. (1983) Solution conformation of biantennary complex type oligosaccharides. FEBS Lett., 164, 231-235.
27. Homans, S.W., Dwek, R.A., Boyd, J., Mahmoudian, M., Richards, W.G. and Rademacher, T.W. (1986) Conformational transitions in N-linked oligosaccharides. Biochemistry, 25, 6342-6350.
28. Homans, S.W., Dwek, R.A. and Rademacher, T.W. (1987a) Tertiary structure in N-linked oligosaccharides. Biochemistry, 26, 6553-6560.
29. Homans, S.W., Dwek, R.A. and Rademacher, T.W. (1987b) Solution conformations of N-linked oligosaccharides. Biochemistry, 26, 6571-6578.
30. Hori, H., Nishida, Y., Ohrui, H., Meguro, H. and Uzawa, J. (1988) Conformational analyses of α and β(1-6) mannodisaccharides by deuterium substitution effect on relaxation rate and NOE. Tetrahedron Lett., 29, 4457-4460.
31. Hubbard, S.C. (1987) Differential effects of oncogenic transformation on N-linked oligosaccharide processing at individual glycosylation sites of viral glycoproteins. J. Biol. Chem., 262, 16403-16411.
32. Imberty, A., Gerber, S., Tran, V. and Pérez, S. (1990) Data bank of three-dimensional structures of disaccharides, a tool to build 3-D structures of oligosaccharides. Glycoconjugate J., 7, 27-54.
33. Imberty, A., Delage, M.-M., Bourne, Y., Cambillau, C. and Pérez, S. (1991) Data bank of three-dimensional structures of dissacharides. II. N-Acetyllactosaminic type N-glycans. Comparison with the crystal structure of a biantennary octasaccharide. Glycoconjugate J., 8, 456-483.
34. Ishii, K., Iwasaki, M., Inoue, S., Kenny, P.T.M., Komura, H. and Inoue, Y. (1989) Free sialooligosaccharides found in the unfertilized eggs of a freshwater trout, Plecoglossus altivelis. J Biol. Chem., 264, 1623-1630.
35. Lindh, I. and Hindsgaul, O. (1991) Synthesis and enzymatic evaluation of two conformationally restricted trisaccharide analogues as substrates for N-acetylglucosaminyltransferase V. J. Am. Chem. Soc., 113, 216-223.
36. 1H spin-spin coupling constants in proteins. Biochem. Biophys. Res. Commun., 113, 967-974.
37. Mazurier, J., Dauchez, M., Vergoten, G., Montreuil, J. and Spik, G. (1991) Molecular modeling of a disialylated monofucosylated biantennary glycan of the N-acetyllactosamine type. Glycoconjugate J., 8, 390-399.
38. Nimtz, M., Martin, W., Wray, V., Klöppel, K.-D., Augustin, J. and Conradt, H.S. (1993) Structures of sialylated oligosaccharides of human erythropoietin expressed in recombinant BHK-21 cells. Eur. J. Biochem., 213, 39-56.
39. 1H-NMR studies on (6R)-and (6S)-deuterated (1-6)-linked disaccharides: assignment of the preferred rotamers about C5-C6 bond of (1-6)-disaccharides in solution. Tetrahedron Lett., 26, 3251-3254.
40. Palcic, M.M., Ripka, J., Kaur, K.J., Shoreibah, M., Hindsgaul, O. and Pierce, M. (1990) Regulation of N-acetylglucosaminyltransferase V activity. Kinetic comparisons of parental, rous sarcoma virus-transformed BHK, and L-phytohemagglutinin-resistant BHK cells using synthetic substrates and an inhibitory substrate analog. J. Biol. Chem., 265, 6759-6769.
41. Pierce, M. and Arango, J. (1986) Rous sarcoma virus-transformed baby hamster kidney cells express higher levels of asparagine-linked tri-and tetraantennary glycopeptides containing [GlcNAc-β(1,6)Man-α(1,6)Man] and poly-N-acetyllactosamine sequences than baby hamster kidney cells. J. Biol. Chem., 261, 10772-10777.
42. 1H NMR spectra proteins via double quantum filtering. Biochem. Biophys. Res. Commun., 117, 479-485.
43. Santer, U.V., Gilbert, F. and Glick, M.C. (1984) Change in glycosylation of membrane glycoproteins after transfection of NIH 3T3 with human tumor DNA. Cancer Res., 44, 3730-3735.
44. Shaka, A.J. and Freeman, R. (1983) Simplification of NMR spectra by filtration through multiple-quantum coherence. J. Magn. Reson., 51, 169-173.
45. Taguchi, T., Seko, A., Kitajima, K., Inoue, S., Iwamatsu, T., Khoo, K.-H., Morris, H.R., Dell, A. and Inoue, Y. (1993) Structural studies of a novel type of tetraantennary sialoglycan unit in a carbohydrate-rich glycopeptide isolated from the fertilized eggs of Indian Medaka fish, Oryzias melastigma. J. Biol. Chem., 268, 2353-2362.
46. Taguchi, T., Kitajima, K., Muto, Y., Yokoyama, S., Inoue, S. and Inoue, Y. (1995a) Proton NMR study of the trimannosyl unit in a pentaantennary N-linked decasaccharide structure. Complete assignment of the proton resonances and conformational characterization. Eur. J. Biochem., 228, 822-829.
47. 13C NMR resonances to all the carbon atoms of the trimannosido-di-N-acetylchitobiosyl structure in a pentaantennary decasacharide glycopeptide. Carbohydr. Res., 275, 185-191.
48. van den Eijnden, D.H., Koenderman, A.H.L. and Schiphorst, W.E.C.M. (1988) Biosynthesis of blood group i-active polylactosaminoglycans. Partial purification and properties of an UDP-GlcNAc:N-acetyllactosaminide β1→3-N-acetylglucosaminyltransferase from Novikoff tumor cell ascites fluid. J. Biol. Chem., 263, 12461-12471.
49. 13C resonance assignments for an octa-and decasaccharide of the N-acetyllactosamine type by multiple-step relayed correlation and hetero-nuclear correlation nuclear magnetic resonance. Glycoconjugate J., 6, 183-194.
50. Yamashita, K., Ohkura, T., Tachibana, Y., Takasaki, S. and Kobata, A. (1984) Comparative study of the oligosaccharides released from baby hamster kidney cells and their polyoma transformant by hydrazinolysis. J. Biol. Chem., 259, 10834-10840.
51. Yamashita, K., Tachibana, Y., Ohkura, T. and Kobata, A. (1985) Enzymatic basis for the structural changes of asparagine-linked sugar chains of membrane glycoproteins of baby hamster kidney cells induced by polyoma transformation. J. Biol. Chem., 260, 3963-3969.