In vitro glycosylation of proteins: An enzymatic approach

Journal of Biotechnology

Volumn 46, Issue 1, 1996, Pages 1-14

  Meynial Salles, Isabelle ^a   Combes, Didier ^a  

^a CNRS   (France)

Author keywords

Biological function of glycoprotein; Biosynthesis pathway; Glycoprotein; Glycosidase; Glycosylation engineering; Glycosyltransferase

Indexed keywords

BIOSYNTHESIS; CELL CULTURE; CELLS; CHARACTERIZATION; DRUG PRODUCTS; ENZYMES; MOLECULAR STRUCTURE; PHYSIOLOGY;

GALACTOSYLTRANSFERASE; GLYCOPROTEINS; GLYCOSIDASES; GLYCOSYLATION; GLYCOSYLTRANSFERASES; OLIGOSACCHARIDE;

PROTEINS;

GLYCOPROTEIN; GLYCOSIDASE; GLYCOSYLTRANSFERASE; RECOMBINANT PROTEIN;

ARTICLE; BIOENGINEERING; BIOSYNTHESIS; BIOTECHNOLOGY; GLYCOSYLATION; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROCESSING;

EID: 0342832972     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/0168-1656(95)00174-3     Document Type: Short Survey

References (89)

1. Abbadi, A., Mcharfi, M., Aubry, A., Premila, S., Boussard, G. and Marraud, M. (1991) Involvement of side functions in peptide structures: the Asx turn. Occurrence and conformational aspects. J. Am. Chem. Soc. 113, 2729-2735.
2. Abeijon, C. and Hirschberg, C. (1992) Topography of glycosylation reactions in the endoplasmic reticulum. Trends Biochem. Sci. 17, 33-36.
3. Ajisaka, K., Nishida, H. and Fujimoto, H. (1987a) The synthesis of oligosaccharides by the reversed hydrolysis reaction of β-glucosidase at high substrate concentration and at high temperature. Biotechnol. Lett. 9, 243-248.
4. Ajisaka, K., Nishida, H. and Fujimoto, H. (1987b) Use of an activated carbon column for the synthesis of disaccharides by use of a reversed hydrolysis activity of β-galactosidase. Biotechnol. Lett. 9, 387-392.
5. Alvarado, E., Nukada, T., Ogawa, T. and Ballou, C.E. (1991) Conformation of the glucotriose unit in the lipid linked oligosaccharide precursor for protein glycosylation. Biochemistry 30, 881-886.
6. Angel, A.S., Grönberg, G., Krotkiewski, H., Lisowska, E. and Nilsson, B. (1991) Structural analysis of the N-linked oligosaccharides from murine glycophorin. Arch. Biochem. Biophys. 291, 76-88.
7. Aubert, J.P., Biserte, G. and Loucheux-Levebvre, M.H. (1976) Carbohydrate-peptide linkage in glycoproteins. Arch. Biochem. Biophys. 175, 410-418.
8. Bause, E. (1984) Model studies on N-glycosylation of proteins. Biochem. Soc. Trans. 12, 514-517.
9. Bause, E. and Hettkamp, H. (1979) Primary structural requirements for N-glycosylation of peptides in rat liver. FEBS Lett. 108, 341-344.
10. Beyer, T.A., Sadler, J.E., Rearick, J.I., Paulson, J.C. and Hill, R.L. (1981) Glycosyltransferases and their use in assessing oligosaccharides structure and structure-function relationships. Adv. Enzymol. 52, 56-69.
11. Carlstedt, I., Sheehan, J.K., Corfield, A.P. and Gallagher, J.T. (1985) Mucous glycoproteins: a gel of a problem. Essays Biochem. 20, 40-76.
12. Carson, D.D., (1992) Proteoglycans in development. In: Fukuda, M. (Ed.), Cell Surface Carbohydrates and Cell Development. CRC Press, London, pp. 257-274.
13. Chou, C.F., Smith, A.J. and Omary, M.B. (1992) Characterization and dynamics of O-linked glycosylation of human cytokeratin 8 and 18. J. Biol. Chem. 267, 3901-3906.
14. Cumming, D.A. (1991) Glycosylation of recombinant protein therapeutics: control and functional implications. Glycobiology 1, 115-130.
15. Cumming, D.A. (1992) Physiological relevance of protein glycosylation. Dev. Biol. Stand. 76, 83-94.
16. Cummings, R.D., Merkle, R.K. and Stults, N.L. (1989) Separation and analysis of glycoprotein oligosaccharides. Methods Cell Biol. 32, 141-183.
17. Dahms, N.M. and Hart, G.W. (1986) Influence of quaternary structure on glycosylation. J. Biol. Chem. 261, 13186-13196.
18. Das, R.C. and Heath, E.C. (1980) Dolichyldiphosphoryloligosaccharide-protein oligosaccharyltransferase: solubilization, purification, and properties. Proc. Natl. Acad. Sci USA 77, 3811-3815.
19. David, S., Augé, C. and Gautheron, C. (1991) Enzymic methods in preparative carbohydrate chemistry. Adv. Carbohydr. Chem. Biochem. 49, 175-237.
20. Dwek, R.A., Edge, C.J., Harvey, D.J., Wormald, M.R. and Parekh, R.B. (1993) Analysis of glycoprotein associated oligosaccharides. Annu. Rev. Biochem. 62, 65-100.
21. Ebner, K.E. (1973) Lactose synthetase. In: Boyer, P.D. (Ed.), The Enzymes, third edition. Academic Press Inc., New York, pp. 363-377.
22. Gavel, Y. and von Heijne, G. (1990) Sequence differences between glycosylated and non-glycosylated Asn-X-Thr/Ser acceptor sites: implications for protein engineering. Protein Eng. 3, 433-442.
23. Gooche, C.F. and Monica, T. (1990) Environmental effects on protein glycosylation. Bio/Technology 8, 421-427.
24. Gyrax, D., Spies, P., Winkler, T. and Pfaar, U. (1991) Enzymatic synthesis of β-D-glucuronides with in situ regeneration of uridine-5′-diphosphoglucuronic acid. Tetrahedron 47, 5119-5122.
25. Harris, R.J., Leonard, C.K., Guzzeta, A.W. and Spellman, M.W. (1991) Tissue plasminogen activator has an O-linked fucose attached to threonine 61 in the epidermal growth factor domain. Biochemistry 30, 2311-2314.
26. Hart, G.W., Haltiwanger, R.S., Holt, G.D. and Kelly, W.G. (1989) Glycosylation in the nucleus and cytoplasm. Annu. Rev. Biochem. 58, 841-874.
27. Hill, R.L. and Brew, K. (1975) Lactose synthetase. Adv. Enzymol. 43, 411-484.
28. Holt, G.D., Haltiwanger, R.S., Torrest, C.R. and Hart, G.W. (1987a) Erythrocytes contain cytoplasmic glycoproteins. J. Biol. Chem. 262, 14847-14850.
29. Holt, G.D., Snow, C.M., Senior, A., Haltiwanger, R.S., Gerace, L. and Hart, G.W. (1987b) Nuclear pore complex glycoproteins contain cytoplasmically disposed O-linked N-acetylglucosamine. J. Cell Biol. 104, 1157-1164.
30. Hubbard, S.C. and Ivatt, R.J. (1981) Synthesis and processing of asparagine-linked oligosaccharides. Annu. Rev. Biochem. 50, 555-583.
31. Hughes, R.C. (1991) Processing and reprocessing of asparagine linked oligosaccharide. In: Conradt, H.S. (Ed.), Protein Glycosylation: Cellular, Biotechnological and Analytical Aspects. VCH Publishers, Weinheim, pp. 3-11.
32. Ichikawa, Y., Look, G.C. and Wong, C.H. (1992) Enzyme catalyzed oligosaccharide synthesis. Anal. Biochem. 202, 215-238.
33. Imperiali, B., Shannon, K.L., Unno, M. and Rickert, K.W. (1992) A mechanistic proposal for asparagine-linked glycosylation. J. Am. Chem. Soc. 114, 7944-7945.
34. Jenkins, N. and Curling, E.M.A. (1994) Glycosylation of recombinant proteins: problems and prospects. Enzyme Microb. Technol. 16, 354-364.
35. Jentoft, N. (1990) Why are proteins O-glycosyled? Trends Biochem. Sci. 15, 291-294.
36. Johansson, E., Hedbys, L. and Larsson, P.O. (1991) Enzymatic synthesis of monosaccharide-amino acid conjugates. Enzyme Microb. Technol. 13, 781-787.
37. Johansson, E., Hedbys, L., Mosbach, K. and Larsson, P.O. (1989) Studies of the reversed a-mannosidase reaction in high concentrations of mannose. Enzyme Microb. Technol. 11, 347-353.
38. Joziasse, D.H. (1992) Mammalian glycosyltransferases: genomic organization and protein structure. Glycobiology 2, 271-277.
39. Kadowaki, S., Yamamoto, K., Fujisaki, M. and Tochikura, T. (1991) Microbial endo-β-N-acetylglucosaminidases acting on complex type sugar chains of glycoproteins. J. Biochem. 110, 17-21.
40. Kaplan, H.A., Welply, J.K. and Lennarz, W.L. (1987) Oligosaccharyl transferase: the central enzyme in the pathway of glycoprotein asssembly. Biochem. Biophys. Acta 906, 161-173.
41. Kapoor, T.M. (1990) Purification and Characterization of the Oligosaccharyl Transferase. Master Report, Lawrence Livermore National Laboratory, Livermore, USA.
42. Kearse, K.P. and Hart, G.W. (1991) Topology of O-linked N-acetylglucosamine in murine lymphocytes. Arch. Biochem. Biophys. 290, 543-548.
43. Kelleher, D.J., Kreibich, G. and Gilmore, R. (1992) Oligosaccharyltransferase activity is associated with a protein complex composed of Ribophorins I and II and a 48 KD protein. Cell 69, 55-65.
44. Kimura, Y., Nakagawa, Y., Tokuda, T., Yamai, M., Nakajima, S., Higashide, E. and Takagi, S. (1992) Structures of N-linked oligosaccharides of microsomal glycoproteins from developing castor bean endosperms. Biosci. Biotech. Biochem. 56, 215-222.
45. Kobata, A. and Takasaki, S. (1992) Structure and biosynthesis of cell surface carbohydrates. In: Fukuda, M. (Ed.), Cell Surface Carbohydrates and Cell Development. CRC Press, London, pp. 1-24.
46. Korf, U. and Thiem, J. (1992) Chemoenzymatic approaches in carbohydrate synthesis. Kontakte (Darmstadt) 1, 3-10.
47. Kornfeld, R. and Kornfeld, S. (1976) Comparative aspects of glycoprotein structure. Annu. Rev. Biochem. 45, 217-237.
48. Kornfeld, R. and Kornfeld, S. (1985) Assembly of asparagine-linked oligosaccharides. Annu. Rev. Biochem. 54, 631-664.
49. Lechner, J. and Wieland, F. (1989) Structure and biosynthesis of prokaryotic glycoproteins. Annu. Rev. Biochem. 58, 173-194.
50. Lehle, L. and Tanner, W. (1976) The specific site of tunicamycin inhibition of dolichol-bound N-acetylglucosamine derivatives. FEBS Lett. 71, 167-170.
51. Lehle, L. and Tanner, W. (1983) Polyprenol-linked sugars and glycoprotein synthesis in plants. Biochem. Soc. Trans. 11, 568-574.
52. Lennarz, W.J. (1975) Lipid linked sugars in glycoprotein synthesis. Science 188, 986-991.
53. Liu, D.T.Y. (1992) Glycoprotein pharmaceuticals: scientific and regulatory considerations, and the US Orphan Drug Act. Trends Biotechnol. 10, 114-119.
54. Lowe, J.B. (1991) Molecular cloning, expression, and uses of mammalian glycosyltransferases. Cell Biol. 2, 289-307.
55. Marshall, R.D. (1974) The nature and metabolism of the carbohydrate-peptide linkages of glycoproteins. In: Smellie, R.M.S. and Beeley, J.G. (Eds.), The Metabolism and Function of Glycoproteins. Biochemical Society, London, pp. 17-26.
56. Merkle, R.K., Heiland, D.E., Welles, J.L., Shilatifard, A., Haseltine, W.A. and Cummings, R.D. (1991) Gp 160 of HIV synthesized by persistently infected molt-3 cells is terminally glycosylated: evidence that cleavage of gp 160 occurs subsequent to oligosaccharide processing. Arch. Biochem. Biophys. 290, 248-257.
57. Montreuil, J. (1980) Primary structure of glycoprotein glycans: basis for the molecular biology of glycoproteins. Adv. Carbohydr. Chem. Biochem. 37, 157-223.
58. Montreuil, J. (1993) Naissance de la glycobiologie. Biofutur 125, 8-11.
59. Montreuil, J., Bouquelet, S., Debray, H., Fournet, B., Spik, G. and Strecker, G. (1986) Glycoproteins. In: Chaplin, M.F. and Kennedy, J.F. (Eds.), Carbohydrate Analysis. IRL Press, Oxford, pp. 143-204.
60. Morosoli, R., Lecher, P. and Durand, S. (1991) A newly described role for protein glycosylation: starved yeast cells absorb their under-glycosylated secreted xylanase faster than the glycosylated enzyme. FEMS Microbiol. Lett. 82, 153-156.
61. Nilsson, K.G.I. (1988) Enzymatic synthesis of oligosaccharides. Trends Biotechnol. 6, 256-264.
62. Nishida, Y., Wiemann, T. and Thiem, J. (1992) Transfer of galactose to the anomeric position of N-acetyl gentosamine by galactosyltransferase from bovine milk. Tetrahedron Lett. 33, 8043-8046.
63. Nishida, Y., Wiemann, T. and Thiem, J. (1993a) Extension of the bGa11,1transfer to N-acetyl-5-thiogentosamine by galactosyltransferase. Tetrahedron Lett. 34, 2905-2906.
64. Nishida, Y., Wiemann, T., Sinnwell, V. and Thiem, J. (1993b) A new type of galactosyltransferase reaction: transfer of galactose to the anomeric position of N-acetylkanosamine. J. Am. Chem. Soc. 115, 2536-2537.
65. O'Connell, B., Tabak, L.A. and Ramasubbu, N. (1991) The influence of flanking sequences on O-glycosylation. Biochem. Biophys. Res. Commun. 180, 1024-1030.
66. O'Connell, B., Hagen, F.K. and Tabak, L. (1992) The influence of flanking sequence on the O-glycosylation of threonine in vitro. J. Biol. Chem. 267, 25010-25018.
67. Ohrlein, R., Ernst, B. and Berger, E.G. (1992) Galactosylation of non natural glycosides with human β-D-galactosyltransferase on a preparative scale. Carbohydr. Res. 236, 335-338.
68. Olden, K.,. Parent, J.B. and White, S.L. (1982) Carbohydrate moieties of glycoproteins a re-evaluation of their function. Biochim. Biophys. Acta 650, 209-232.
69. Palcic, M.M. and Hindsgaul, O. (1991) Flexibility in the donor substrate specificity of β-1,4-galactosyltransferase: application in the synthesis of complex carbohydrates. Glycobiology 1, 205-209.
70. Parekh, R.B. (1991) Mairmalian cell gene expression: protein glycosylation. Curr. Opin. Biotechnol. 2, 730-734.
71. Parodi, A.J. and Leloir, L.L., (1979) The role of lipid intermediates in the glycosylation of proteins in the eukaryotic cell. Biochim. Biophys. Acta. 559, 1-37.
72. Paulson, J.C. and Colley, K.J. (1989) Glycosyltransferases: structure, localization, and control of cell type-specific glycosylation. J. Biol. Chem. 264, 17615-17618.
73. Rademacher, T.W., Parekh, R.B. and Dwek, R.A. (1988) Glycobiology. Annu. Rev. Biochem. 57, 785-838.
74. Rose, G.D., Gierasch, L.M. and Smith, J.A. (1985) Turns in peptides and proteins. Adv. Protein Chem. 37, 85-87.
75. Sharon, N. (1984) Glycoproteins. Trends Biochem. Sci., April, 198-202.
76. Spiro, R.G. (1973) Glycoproteins. Adv. Protein Chem. 27, 349-454.
77. Stanley, P. (1992) Glycosylation engineering. Glycobiology 2, 99-107.
78. Sturgeon, R.J. (1988) The glycoproteins and glycogen. In: Kennedy, J.F. (ed.), Carbohydrate Chemistry. Oxford Science Publication, Oxford, pp. 263-302.
79. Tanner, W. and Lehle, L. (1987) Protein glycosylation in yeast. Biochim. Biophys. Acta 906, 81-89.
80. Thiem, J. and Wiemann, T. (1991) Galactosyltransferase catalyzed synthesis of 2′-deoxy-N-acetyllactosamine. Angew Chem. Int. Ed. Eng. 30, 1163-1164.
81. Toone, E.J., Simon, E.S., Bednarski, M.D. and Whitesides, G.M. (1989) Enzyme catalyzed synthesis of carbohydrates. Tetrahedron 45, 5365-5422.
82. Turco, S.J., Stetson, B., Robbins, P.W. (1977) Comparative rates of transfer of lipid linked oligosaccharides to endogenous glycoprotein acceptors in vitro. Proc. Natl. Acad. Sci. USA 74, 4411-4414.
83. Verbert, A. (1993) La glycosylation des protéines recombinantes. Biofutur 125, 40-44.
84. Waechter, C.J. and Lennarz, W.J. (1976) The role of polyprenol-linked sugars in glycoprotein synthesis? Annu. Rev. Biochem. 45, 95-113.
85. Wang, Y., Abernethy, J.L., Eckhardt, A.E. and Hill, R.L. (1992) Purification and characterization of a UDP-galNac: polypeptide N-acetylgalactosaminyltransferase specific for glycosylation of threonine residues. J. Biol. Chem. 267, 12709-12716.
86. Whitaker, J.R. (1977) Enzymatic modification of proteins applicable to foods. In: Food Proteins. Adv. Chem. Series 160, 126-134.
87. Whiteheart, S.W., Passaniti, A., Reichner, J.S., Holt, G.D., Haltiwanger, R.S. and Hart, G.W. (1989) Glycosyltransferase probes. Methods Enzymol. 179, 83-95.
88. Wong, C.H. (1992) Engineering enzymes for chemoenzymatic synthesis. Trends Biotechnol. 10, 337-341.
89. Wong, C.H., Ichikawa, Y., Krach, T., Gautheron-Le-Narvor, C., Dumas, D.P. and Look, G.C. (1991) Probing the acceptor specificity of β-1,4-galactosyltransferase for the development of enzymatic synthesis of novel oligosaccharides. J. Am. Chem. Soc. 113, 8137-8145.