Metabolic functionalization of recombinant glycoproteins

Biochemistry

Volumn 43, Issue 38, 2004, Pages 12358-12366

  Luchansky, Sarah J ^a   Argade, Sulabha ^c   Hayes, Bradley K ^c   Bertozzi, Carolyn R ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOHYDRATES; CHEMICAL MODIFICATION; MEMBRANES; METABOLISM;

GLYCOPROTEINS; OLIGOSACCHARIDE ENGINEERING;

PROTEINS;

AMINO ACID; AZIDE; CARBOHYDRATE; CARBOHYDRATE DERIVATIVE; FUNCTIONAL GROUP; GLYCAN; GLYCOPROTEIN; IMMUNOGLOBULIN G; MANNOSAMINE; N AZIDOACETYLMANNOSAMINE; N AZIDOACETYLSIALIC ACID; NITROGEN; OLIGOSACCHARIDE; OXYGEN; RECOMBINANT GAMMA INTERFERON; RECOMBINANT GLYCOPROTEIN; SIALIC ACID; SIALOSIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CARBOHYDRATE METABOLISM; CELL COMMUNICATION; CELL TYPE; CHEMICAL ENGINEERING; CHEMICAL MODIFICATION; CONTROLLED STUDY; DERIVATIZATION; DRUG EFFICACY; DRUG METABOLISM; HUMAN; HUMAN CELL; MEMBRANE BINDING; MOUSE; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; PROTEIN SECRETION; STAUDINGER REACTION;

ANIMALS; AZIDES; CELL LINE; CERCOPITHECUS AETHIOPS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; GENE EXPRESSION; GLYCOPROTEINS; HUMANS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; N-ACETYLNEURAMINIC ACID; OLIGOSACCHARIDES; RECOMBINANT PROTEINS;

ANIMALIA;

EID: 4644344901     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi049274f     Document Type: Article

References (54)

1. Lowe, J. B. (2003) Glycan-dependent leukocyte adhesion and recruitment in inflammation, Curr. Opin. Cell Biol. 15, 531-538.
2. Renauld, J. C. (2003) Class II cytokine receptors and their ligands: key antiviral and inflammatory modulators, Nat. Rev. Immunol. 3, 667-676.
3. Hollingsworth, M. A., and Swanson, B. J. (2004) Mucins in cancer: protection and control of the cell surface, Nat. Rev. Cancer 4, 45-60.
4. Vestweber, D., and Blanks, J. E. (1999) Mechanisms that regulate the function of the selectins and their ligands, Physiol. Rev. 79, 181-213.
5. Cracker, P. R., and Varki, A. (2001) Siglecs in the immune system, Immunology 103, 137-145.
6. Lowe, J. B. (2001) Glycosylation, immunity, and autoimmunity, Cell 104, 809-812.
7. Torchilin, V. P., and Lukyanov, A. N. (2003) Peptide and protein drug delivery to and into tumors: challenges and solutions, Drug Discov. Today 8, 259-266.
8. Davis, B. G. (2004) Mimicking posttranslational modifications of proteins, Science 303, 480-482.
9. Burke, P. A., and Putney, S. D. (2001) in Recombinant Protein Drugs (Buckel, P., Ed.) pp 151-168, Birkhauser Verlag, Boston.
10. Cumming, D. A. (1991) Glycosylation of recombinant protein therapeutics: control and functional implications, Glycobiology 1, 115-130.
11. Elliott, S., Lorenzini, T., Asher, S., Aoki, K., Brankow, D., Buck, L., Busse, L., Chang, D., Fuller, J., Grant, J., Hernday, N., Hokum, M., Hu, S., Knudten, A., Levin, N., Komorowski, R., Martin, F., Navarro, R., Osslund, T., Rogers, G., Rogers, N., Trail, G., and Egrie, J. (2003) Enhancement of therapeutic protein in vivo activities through glycoengineering, Nat. Biotechnol. 21, 414-421.
12. Koury, M. J. (2003) Sugar coating extends half-lives and improves effectiveness of cytokine hormones, Trends Biotechnol. 21, 462-464.
13. Kochendoerfer, G. G., Chen, S. Y., Mao, F., Cressman, S., Traviglia, S., Shao, H., Hunter, C. L., Low, D. W., Cagle, E. N., Carnevali, M., Gueriguian, V., Keogh, P. J., Porter, H., Stratton, S. M., Wiedeke, M. C., Wilken, J., Tang, J., Levy, J. J., Miranda, L. P., Crnogorac, M. M., Kalbag, S., Botti, P., Schindler-Horvat, J., Savatski, L., Adamson, J. W., Kung, A., Kent, S. B., and Bradburne, J. A. (2003) Design and chemical synthesis of a homogeneous polymer-modified erythropoiesis protein, Science 299, 884-887.
14. Monfardini, C., and Veronese, F. M. (1998) Stabilization of substances in circulation, Bioconjugate Chem. 9, 418-450.
15. Wilchek, M., Spiegel, S., and Spiegel, Y. (1980) Fluorescent reagents for the labeling of glycoconjugates in solution and on cell surfaces, Biochem. Biophys. Res. Commun. 92, 1215-1222.
16. Spiegel, S. (1987) Fluorescent gangliosides, Methods Enzymol. 138, 313-318.
17. Sytkowski, A. J., Lunn, E. D., Davis, K. L., Feldman, L., and Siekman, S. (1998) Human erythropoietin dimers with markedly enhanced in vivo activity, Proc. Natl. Acad. Sci. U.S.A. 95, 1184-1188.
18. Dalle, B., Henri, A., Rouyer-Fessard, P., Bettan, M., Scherman, D., Beuzard, Y., and Payen, E. (2001) Dimeric erythropoietin fusion protein with enhanced erythropoietic activity in vitro and in vivo, Blood 97, 3776-3782.
19. Sytkowski, A. J., Lunn, E. D., Risinger, M. A., and Davis, K. L. (1999) An erythropoietin fusion protein comprised of identical repeating domains exhibits enhanced biological properties, J. Biol. Chem. 274, 24773-24778.
20. Gillies, S. D. (2001) in Recombinant Protein Drugs (Buckel, P., Ed.) pp 129-147, Birkhauser Verlag, Boston.
21. Hang, H. C., and Bertozzi, C. R. (2001) Chemoselective approaches to glycoprotein assembly, Acc. Chem. Res. 34, 727-736.
22. Wang, L., Brock, A., Herberich, B., and Schultz, P. G. (2001) Expanding the genetic code of Escherichia coli, Science 292, 498-500.
23. Nowak, M. W., Kearney, P. C., Sampson, J. R., Saks, M. E., Labarca, C. G., Silverman, S. K., Zhong, W., Thorson, J., Abelson, J. N., Davidson, N., et al. (1995) Nicotinic receptor binding site probed with unnatural amino acid incorporation in intact cells, Science 268, 439-442.
24. Kiick, K. L., and Tirrell, D. A. (2000) Protein engineering by in vivo incorporation of non-natural amino acids: control by incorporation of methionine analogues by methionyl-tRNA synthetase, Tetrahedron 56, 9487-9493.
25. Kiick, K. L., Saxon, E., Tirrell, D. A., and Bertozzi, C. R. (2002) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation, Proc. Natl. Acad. Sci. U.S.A. 99, 19-24.
26. Chin, J. W., Cropp, T. A., Anderson, J. C., Mukherji, M., Zhang, Z., and Schultz, P. G. (2003) An expanded eukaryotic genetic code, Science 301, 964-967.
27. Datta, D., Wang, P., Carrico, I. S., Mayo, S. L., and Tirrell, D. A. (2002) A designed phenylalanyl-tRNA synthetase variant allows efficient in vivo incorporation of aryl ketone functionality into proteins, J. Am. Chem. Soc. 124, 5652-5653.
28. Kayser, H., Zeitler, R., Kannicht, C., Grunow, D., Nuck, R., and Reutter, W. (1992) Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-D-hexosamines as precursors, J. Biol. Chem. 267, 16934-16938.
29. Mahal, L. K., Yarema, K. J., and Bertozzi, C. R. (1997) Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis, Science 276, 1125-1128.
30. Saxon, E., and Bertozzi, C. R. (2000) Cell surface engineering by a modified Staudinger reaction, Science 287, 2007-2010.
31. Hang, H. C., and Bertozzi, C. R. (2001) Ketone isosteres of 2-N-acetamidosugars as substrates for metabolic cell surface engineering, J. Am. Chem. Soc. 123, 1242-1243.
32. Oetke, C., Brossmer, R., Mantey, L. R., Hinderlich, S., Isecke, R., Reutter, W., Keppler, O. T., and Pawlita, M. (2002) Versatile biosynthetic engineering of sialic acid in living cells using synthetic sialic acid analogues, J. Biol. Chem. 277, 6688-6695.
33. Hang, H. C., Yu, C., Kato, D. L., and Bertozzi, C. R. (2003) A metabolic labeling approach towards proteomic analysis of mucin-type O-linked glycosylation, Proc. Natl. Acad. Sci. U.S.A. 100, 14846-14851.
34. Dube, D. H., and Bertozzi, C. R. (2003) Metabolic oligosaccharide engineering as a tool for glycobiology, Curr. Opin. Chem. Biol. 7, 616-625.
35. Keppler, O. T., Horstkorte, R., Pawlita, M., Schmidt, C., and Reutter, W. (2001) Biochemical engineering of the N-acyl side chain of sialic acid: biological implications, Glycobiology 11, 11R-18R.
36. Luchansky, S. J., Hang, H. C., Saxon, E., Grunwell, J. R., Yu, C., Dube, D. H., and Bertozzi, C. R. (2003) Constructing azide-labeled cell surfaces using polysaccharide biosynthetic pathways, Methods Enzymol. 362, 249-272.
37. Luchansky, S. J., Goon, S., and Bertozzi, C. R. (2004) Expanding the diversity of unnatural cell-surface sialic acids, ChemBioChem 5, 371-374.
38. Bistrup, A., Bhakta, S., Lee, J. K., Belov, Y. Y., Gunn, M. D., Zuo, F. R., Huang, C. C., Kannagi, R., Rosen, S. D., and Hemmerich, S. (1999) Sulfotransferases of two specificities function in the reconstitution of high endothelial cell ligands for L-selectin, J. Cell Biol. 145, 899-910.
39. Kuster, B., Wheeler, S. F., Hunter, A. P., Dwek, R. A., and Harvey, D. J. (1997) Sequencing of N-linked oligosaccharides directly from protein gels: in-gel deglycosylation followed by matrix-assisted laser desorption/ionization mass spectrometry and normal-phase high-performance liquid chromatography, Anal. Biochem. 250, 82-101.
40. Ausubel, F. M., Brent, R., Kingston, R. E., Moore, D. D., Seidman, J. G., Smith, J. A., Strahl, K., Albright, L. M., Coen, D. M., and Varki, A. (1993) Preparation and Analysis of Glycoconjugates, in Current Protocols in Molecular Biology (Chanda, V. B., Ed.) John Wiley & Sons, New York.
41. Saxon, E., Luchansky, S. J., Hang, H. C., Yu, C, Lee, S. C., and Bertozzi, C. R. (2002) Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation, J. Am. Chem. Soc. 124, 14893-14902.
42. Luchansky, S. J., Yarema, K. J., Takahashi, S., and Bertozzi, C. R. (2003) GlcNAc 2-epimerase can serve a catabolic role in sialic acid metabolism, J. Biol. Chem. 278, 8035-8042.
43. Mahal, L. K., Charter, N. W., Angata, K., Fukuda, M., Koshland, D. E., Jr., and Bertozzi, C. R. (2001) A small-molecule modulator of poly-α 2,8-sialic acid expression on cultured neurons and tumor cells, Science 294, 380-382.
44. Yong, V. W., Chabot, S., Stuve, O., and Williams, O. (1998) Interferon β in the treatment of multiple sclerosis: mechanisms of action, Neurology 51, 682-689.
45. Conradt, H. S., Egge, H., Peter-Katalinic, J., Reiser, W., Siklosi, T., and Schaper, K. (1987) Structure of the carbohydrate moiety of human interferon-β secreted by a recombinant Chinese hamster ovary cell line, J. Biol. Chem. 262, 14600-14605.
46. Kagawa, Y., Takasaki, S., Utsumi, J., Hosoi, K., Shimizu, H., Kochibe, N., and Kobata, A. (1988) Comparative study of the asparagine-linked sugar chains of natural human interferon-β 1 and recombinant human interferon-β 1 produced by three different mammalian cells, J. Biol. Chem. 263, 17508-17515.
47. Imai, Y., Singer, M. S., Fennie, C., Lasky, L. A., and Rosen, S. D. (1991) Identification of a carbohydrate-based endothelial ligand for a lymphocyte homing receptor, J. Cell Biol. 113, 1213-1221.
48. Hemmerich, S., Leffler, H., and Rosen, S. D. (1995) Structure of the O-glycans in GlyCAM-1, an endothelial-derived ligand for L-selectin, J. Biol. Chem. 270, 12035-12047.
49. Lasky, L. A., Singer, M. S., Dowbenko, D., Imai, Y., Henzel, W. J., Grimley, C., Fennie, C., Gillett, N., Watson, S. R., and Rosen, S. D. (1992) An endothelial ligand for L-selectin is a novel mucin-like molecule, Cell 69, 927-938.
50. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew. Chem., Int. Ed. 41, 2596-2599.
51. Hong, Y., and Stanley, P. (2003) Lec3 Chinese hamster ovary mutants lack UDP-N-acetylglucosamine 2-epimerase activity because of mutations in the epimerase domain of the One gene, J. Biol. Chem. 278, 53045-53054.
52. Keppler, O. T., Hinderlich, S., Langner, J., Schwartz-Albiez, R., Reutter, W., and Pawlita, M. (1999) UDP-GlcNAc 2-epimerase: A regulator of cell surface sialylation, Science 284, 1372-1376.
53. Jacobs, C. L., Yarema, K. Y., Mahal, L. K., Nauman, D. A., Charters, N. W., and Bertozzi, C. R. (2000) Metabolic labeling of glycoproteins with chemical tags through unnatural sialic acid biosynthesis, Methods Enzymol. 327, 260-275.
54. Sarkar, A. K., Fritz, T. A., Taylor, W. H., and Esko, J. D. (1995) Disaccharide uptake and priming in animal cells: inhibition of sialyl Lewis X by acetylated Gal β 1→4GlcNAc β-O-naphthalenemethanol, Proc. Natl. Acad. Sci. U.S.A. 92, 3323-3327.