NMR investigations of the role of the sugar moiety in glycosylated recombinant human granulocyte-colony-stimulating factor

European Journal of Biochemistry

Volumn 247, Issue 1, 1997, Pages 386-395

  Gervais, Virginie ^a   Zerial, Aurelio ^b   Oschkinat, Hartmut ^a,c,d  

^a EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^b SANOFI   (France)

^c LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^d Europ Molec Biology Organization   (Germany)

Author keywords

Carbohydrate structure analysis; Glycoproteins; NMR; O linked oligosaccharides

Indexed keywords

GLYCOPROTEIN; RECOMBINANT GRANULOCYTE COLONY STIMULATING FACTOR;

ANIMAL CELL; ARTICLE; CARBOHYDRATE ANALYSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

ANIMALIA;

EID: 0030745180     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00386.x     Document Type: Article

References (60)

1. Abeygunawardana, C. & Bush, C. A. (1991) Complete structure of the cell surface polysaccharide of Streptococcus oralis C104: a 600-MHz NMR study, Biochemistry 30, 8568-8577.
2. Asano, S. (1991) Human granulocyte colony-stimulating factor: its basic aspects and clinical applications, Am. J. Pediatr. Hematol. Oncol. 13, 4, 400-413.
3. Baudys, M., Uchio, T., Mix, D., Wilson, D. & Kim, S. W. (1995) Physical stabilization of insulin by glycosylation, J. Pharm. Sci. 84, 28-33.
4. Bergwerff, A. A., Van Oostrum, J., Asselbergs, F. A. M., Urgi, R., Hokke, C. H., Kamerling, J. P. & Vliegenthart, J. F. G. (1993) Primary Structure of N-linked carbohydrates chains of a human chimeric plasminogen activator K2tu-PA expressed in Chinese hamster ovary cells, Eur. J. Biochem. 212, 639-656.
5. Berman, E., Allerhand, A. & DeVries, A. L. (1980) Natural abundance carbon 13 nuclear magnetic resonance spectroscopy of antifreeze glycoproteins, J. Biol. Chem. 255, 4407-4410.
6. Clark, S. C. & Kamen, R. (1987) The human hematopoietic colony-stimulating factors, Science 236, 1229-1237.
7. 1H NMR studies of an Asn-linked glycopeptide, J. Biol. Chem. 269, 3331-3338.
8. 13C HSQC and HSQC-TOCSY to the α subunit of human chorionic gonadotropin, FEBS Lett. 348, 1-6.
9. De Laureto, P. P., Toma, S., Tonon, G. & Fontana, A. (1995) Probing the structure of human growth hormone by limited proteolysis, Int. J. Pept. Protein Res. 45, 200-208.
10. Demchuk, E., Mueller, T., Oschkinat, H., Sebald, W. & Wade, R. C. (1994) Receptor binding properties of four-helix-bundle growth factors deduced from electrostatic analysis, Protein Sci. 3, 920-935.
11. 1H-NMR assignments and folding topology of human CD59, Protein Sci. 2, 2015-2027.
12. Fu, G., Cunningham, B. C., Fukunaga, R., Nagata, S., Goeddel, D. V. & Wells, J. A. (1992) Rational design of potent antagonists to the human growth hormone receptor, Science 256, 1677-1680.
13. 2Hs-glycoprotein, J. Biol. Chem. 258, 4966-4971.
14. Gerken, T. A., Butenhof, K. J. & Shogren, R. (1989) Effects of glycosylation on the conformation and dynamics of O-linked glycoproteins: carbon-13 NMR studies of ovine submaxillary mucin, Biochemistry 28, 5536-5543.
15. Gerken, T. A. & Dearborn, D. G. (1984) Carbon-13 NMR studies of native and modified ovine submaxillary mucin, Biochemistry 23, 1485-1497.
16. Haniu, M., Horan, T., Arakawa, T., Le, J., Katta, V., Hara, S. & Rohde, M. (1996) Disulfide structure and N-glycosylation sites of an extra-cellular domain of granulocyte-colony stimulating factor receptor, Biochemistry 35, 13 040-13 046.
17. Harris, R. J., Van Halbeek, H., Glushka, J., Basa, L. J., Ling, V. T., Smith, K. J. & Spellman, M. W. (1993) Identification and structural analysis of the tetrasaccharide NeuAc(α2-6)Galβ(1-4)GlcNacβ(1-3)Fucα1-O-linked to serine 61 of human factor IX, Biochemistry 32, 6539-6547.
18. Hasegawa, M. (1993) A thermodynamic model for denaturation of granulocyte-colony-stimulating factor: O-linked sugar chain suppresses not the triggering deprotonation but the succeeding denaturation, Biochim. Biophys. Acta 1203, 295-297.
19. Hill, C. P., Osslung, T. D. & Eisenberg, D. (1993) The structure of granulocyte-colony-stimulating factor and its relationship to other growth factors, Proc. Natl Acad. Sci. USA 90, 5167-5171.
20. Hiraoka, O., Anaguchi, H., Yamasaki, K., Fukunaga, R., Nagata, S. & Ota, Y. (1994) ligand binding domain of granulocyte colony-stimulating factor receptor, J. Biol. Chem. 269, 22 412-22 419.
21. Hoglund, M., Bengtsson, M., Cour-Chabernaud, V., Dabouz-Harrouche, F., Simonsson, B., Smedmyr, B. & Totterman, T. (1995) Glycosylated rHuG-CSF is more potent than non-glycosylated rHuG-CSF in mobilisation of peripheral blood progenitor cells (PBPC) in healthy volunteers, Blood 86, Suppl. 1, 464.
22. Hokke, C. H., Damm, J. B. L., Penninkhof, B., Aitken, R. J., Kamerling, J. P. & Vliegenthart, J. F. G. (1994) Structure of the O-Linked carbohydrate chains of porcine zona pellucida glycoprotein, Eur. J. Biochem. 221, 491-512.
23. Horan, T., Wen, J., Narhi, L., Parker, V., Garcia, A., Arakawa, T. & Philo, J. (1996) Dimerization of the extracellular domain of granulocyte-colony stimulating factor receptor by ligand binding: a monovalent ligand induces 2:2 complexes, Biochemistry 35, 4886-4896.
24. Ishikawa, M., Iijima, H., Satake-Ishikawa, R., Tsumura-H, H., Iwamatsu, A., Kadoya, T., Shirnada, Y., Fukamachi, H., Kobayashi, K. & Matsuki, S. (1992) The substitution of cysteine 17 of recombinant human G-CSF with alanine greatly enhanced its stability, Cell Struct. Funct. 17, 61-65.
25. Joao, H. C. & Dwek, R. A. (1993) Effects of glycosylation on protein structure and dynamics in ribonuclease B and some of its individual glycoforms, Eur. J. Biochem. 218, 239-244.
26. Kadkhodaei, M., Hwang, T.-L., Tang, J. & Shaka, A. J. (1993) A simple windowless mixing sequence to supress cross relaxation in TOCSY experiments, J. Magn. Reson. 105, 104-107.
27. Kihlberg, J., Ahman, J., Walse, B., Drackenberg, T., Nilsson, A., Soderberg-alhm, C., Bengtsson, B. & Olsson, H. (1995) Glycosylated peptide hormones: pharmacological properties and conformational studies of analogues of (1 desamino,8-D-arginine) vasopressin, J. Med. Chem. 38, 161-169.
28. Kishita, M., Motojima, M. & Oh-eda, M. (1992) Stability of granulocyte-colony-stimulating factor (rHuG-CSF) in serum. Clin. Rep. 26, 221-224.
29. Krauss, J. H., Himmelspach, K., Reuter, G., Schauer, R. & Mayer, H. (1992) Structural analysis of a novel sialic-acid-containing trisaccharide from Rhodobacter capsulatux 37b4 lipopolysaccharide, Eur. J. Biochem. 204, 217-223.
30. Kubota, N., Orita, T., Hattori, K., Oh-eda, M., Ochi, N. & Yamasaki, T. (1990) Structural characterization of natural and recombinant granulocyte-colony-stimulating factor. J. Biochem. (Tokyo) 107, 486-492.
31. Kwon, K. S., Song, M. & Yu, M. H. (1995) Purification and characterization of alpha 1-antitrypsin secreted by recombinant yeast Saccharomycies diastaticus, J. Biotechnol. 42, 191-195.
32. Lu, H. S., Boone, T. C., Souza, L. M. & Lai, P.-H. (1989) Disulfide and secondary structures of recombinant human granulocyte-colony stimulating factor, Arch. Biochem. Biophys. 268, 81-92.
33. Mendoza, J. & Campo, G. (1996) Ligand-induced conformational changes of GroEl are dependent on the bound substrate polypeptide, J. Biol. Chem. 271, 16 344-16 349.
34. Mer, G., Hietter, H. & Lefevre, J.-F. (1995) Stabilization of proteins by glycosylation examined by NMR analysis of a fucosylated proteinase inhibitor, Nat. Struct. Biol. 3, 45-53.
35. Metcalf, D. (1985) The granulocyte-macrophage colony stimulating factors, Science 229, 16-22.
36. Mire-Sluis, A. R., Tivmamm, H. A., Gaines-Das, R. & Thorpe, R. (1995) The role of glycosylation in the biological activity of Granulocyte-Colony Stimulating Factor, Int. Soc. Exp. Haemat. A461.
37. Mott, H. R. & Campbell, I. D. (1995) Four-helix bundle growth factors and their receptors: protein-protein interactions, Curr. Opin. Struct. Biol. 5, 114-121.
38. Nagata, S. (1989) Gene structure and function of Granulocyte Colony-Stimulating Factor, Bioessays 10, 113-117.
39. Nicholson, S. E., Oates, A. C., Harpur, A. G., Ziemiecki, A., Wills, A. F. & Layton, J. E. (1994) Tyrosine kinase JAK1 is associated with the granulocyte-colony-stimulating factor receptor and both become tyrosine-phosphorylated after receptor activation, Proc. Natl Acad. Sci. USA 91, 2985-2988.
40. Nicola, N. A. (1989) Hemopoietic cell growth factors and their receptors, Annu. Rev. Biochem. 58, 45-77.
41. Nissen, C., Carbonare, V. D. & Moser, Y. (1994) In vitro comparison of the biological potency of glycosylated versus non glycosylated rG-CSF, Drug Invest. 7, 346-352.
42. Nomura, H., Imazeki, I., Oheda, M., Kubota, N., Tamura, M., Ono, M., Ueyama, Y. & Asano, S. (1986) Purification and characterization of human granulocyte-colony-stimulating factor (G-CSF), EMBO J. 5, 871-876.
43. Oh-eda, M., Hase, S., Ono, M. & Ikenaka, T. (1988) Structures of the sugar chains of recombinant human granulocyte-colony-stimulating factor produced by chinese hamster ovary cells, J. Biochem. (Tokyo) 103, 544-546.
44. Oh-eda, M., Hasegawa, M., Hattori, K., Kuboniwa, H., Kojima, T., Orita, T., Tomonou, K., Yamasaki, T. & Ochi, N. (1990) O-Linked sugar chain of human granulocyte-colony stimulating factor protects it against polymerization and denaturation allowing it to retain its biological activity, J. Biol. Chem. 265, 11 432-11 436.
45. Piotto, M., Saudek, V. & Sklenar, V. (1992) Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions, J. Biomol. NMR. 2, 661-665.
46. Plard, J. P., Nohymek, G. J., Wells, M. Y. & Roquet, F. (1995) The biological potency of glycosylated and non glycosylated recombinant granulocyte colony-stimulating factors (rG-CSF) in Sprague-Dawley rats, Int. Soc. Exp. Haemat. A510.
47. Prohaska, R., Koerner, T. A. W., Armitage, I. M. & Furthmayr, H. (1981) Chemical and carbon-13 nuclear magnetic resonance studies of the blood group M and N active sialoglycopeptides from human glycophorin A, J. Biol. Chem. 256, 5781-5791.
48. Reidhaar-Olson, J. F., Zouza-Hart, J. A. D. & Selick, H. E. (1996) Identification of residues critical to the activity of human granulocytecolony stimulating factor, Biochemistry 35, 9034-9041.
49. Rudd, P. M., Joao, H. C., Coghill, E., Fiten, P., Saunders, R., Opdenakker, M. G. & Dwek, R. A. (1994) Glycoforms modify the dynamic stability and functional activity of an enzyme, Biochemistry 33, 17-22.
50. Van Berkel, P. H. C., Geerts, M. E. J., Van Veen, H. A., Kooiman, P. M., Pieper, F. R., De Boer, H. A. & Nuijens, J. H. (1995) Glycosylated and unglycosylated human lactoferrins both bind iron and show identical affinities towards human lysozyme and bacterial lipopolysaccharide, but differ in their susceptibilities toward tryptic proteolysis, Biochem. J. 312, 107-114.
51. 1H-NMR spectroscopy, Eur. J. Biochem. 127, 7-20.
52. 1H-nuclear magnetic resonance spectroscopy as a tool in the structural analysis of carbohydrates related to glycoproteins, Adv. Carbohydr. Chem. Biochem. 41, 209-374.
53. Wade, R. C. & Oschkinat, H. (1996) Influence of glycosylation on the activity of rG-CSFs: in vitro studies: molecular structure and modeling, Int. J. Hematol. 64, Suppl. 2, S7-S8.
54. Wang, C., Eufemi, M., Turano, C. & Giartasio, A. (1996) Influence of the carbohydrate moiety on the stability of glycoproteins, Biochemistry 35, 7299-7307.
55. Werner, J. M., Breeze, A. L., Kara, B., Rosenbrock, G., Boyd, J., Soffe, N. & Campbell, I. D. (1994) Secondary structure and backbone dynamics of human granulocyte colony-stimulating factor, Biochemistry 33, 7184-7192.
56. Worldmann, M. R., Wooten, E. W., Bazzo, R., Edge, C. J., Feinstein, A., Rademacher, T. W. & Swek, R. A. (1991) The conformational effects of N-glycosylation on the tailpiece from serum IgM, Eur. J. Biochem. 198, 131-139.
57. Wyss, D. F., Choi, J. S., Li, J., Knoppers, M. H., Willis, K. J., Arulanandam, A. R. N., Smolyar, A., Reinherz, E. L. & Wagner, G. (1995a) Conformation and function of the N-linked glycan in the adhesion domain of human CD2, Science 269, 1273-1278.
58. Wyss, D. F., Choi, J. S. & Wagner, G. (1995b) Composition and sequence specific resonance assignments of the heterogeneous N-linked glycan in the 13.6 kDa adhesion domain of human CD2 as determined by NMR on the intact glycoprotein, Biochemistry 34, 1622-1634.
59. Zink, T., Ross, A., Ambrosius, D., Rudolph, R. & Holak, T. A. (1992) Secondary structure of human granulocyte colony-stimulating factor from NMR spectroscopy, FEBS Lett. 314, 435-439.
60. Zink, T., Ross, A., Luers, K., Cieslar, C., Rudolph, R. & Holak, T. A. (1994) Structure and dynamics of the human granulocyte colony-stimulating factor determined by NMR spectroscopy loop mobility in a four-helix-bundle protein, Biochemistry 33, 8453-8463.