Protein Glycosylation

Comprehensive Biotechnology, Second Edition

Volumn 3, Issue , 2011, Pages 467-486

  Kattla, J J ^a   Struwe, W B ^a   Doherty, M ^a   Adamczyk, B ^a   Saldova, R ^a   Rudd, P M ^a   Campbell, M P ^b  

^a NATIONAL INSTITUTE FOR BIOPROCESSING RESEARCH AND TRAINING   (Ireland)

^b MACQUARIE UNIVERSITY   (Australia)

Author keywords

Biopharmaceutical glycosylation; Glycan analysis; Glycoanalytics; Glycomics; Glycoprofiling

Indexed keywords

EID: 85012816388     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-08-088504-9.00230-0     Document Type: Chapter

References (87)

1. Apweiler R., Hermjakob H., Sharon N. On the frequency of protein glycosylation, as deduced from analysis of the SWISS-PROT database. Biochimica et Biophysica Acta 1999, 1473(1):4-8.
2. Varki A., Cummings R.D., Esko J.D., et al. Essentials of Glycobiology 2009, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
3. Brooks S.A., Dwek M.W., Schumacher U. Functional & Molecular Glycobiology P. Dines 2002, BIOS Scientific Publishers Limited, Oxford.
4. Kornfeld R., Kornfeld S. Assembly of asparagine-linked oligosaccharides. Annual Review of Biochemistry 1985, 54:631-664.
5. Yamashita K., Kamerling J.P., Kobata A. Structural study of the carbohydrate moiety of hen ovomucoid. Occurrence of a series of pentaantennary complex-type asparagine-linked sugar chains. The Journal of Biological Chemistry 1982, 257(21):12809-12814.
6. Mimura Y., Sondermann P., Ghirlando R., et al. Role of oligosaccharide residues of IgG1-Fc in Fc gamma RIIb binding. The Journal of Biological Chemistry 2001, 276(49):45539-45547.
7. Nimmerjahn F., Ravetch J.V. Fc[gamma] receptors as regulators of immune responses. Nature Reviews. Immunology 2008, 8(1):34-47.
8. Erbayraktar S., Grasso G., Sfacteria A., et al. Asialoerythropoietin is a nonerythropoietic cytokine with broad neuroprotective activity in vivo. Proceedings of the National Academy of Sciences of the United States of America 2003, 100(11):6741-6746.
9. Fukuda M., Sasaki H., Lopez L., Fukuda M. Survival of recombinant erythropoietin in the circulation: The role of carbohydrates. Blood 1989, 73(1):84-89.
10. Arnold J.N., Wormald M.R., Sim R.B., et al. The impact of glycosylation on the biological function and structure of human immunoglobulins. Annual Review of Immunology 2007, 25(1):21-50.
11. Chung C.H., Mirakhur B., Chan E., et al. Cetuximab-induced anaphylaxis and IgE specific for galactose-alpha-1,3-galactose. The New England Journal of Medicine 2008, 358(11):1109-1117.
12. Muchmore E.A., Milewski M., Varki A., Diaz S. Biosynthesis of N-glycolyneuraminic acid. The primary site of hydroxylation of N-acetylneuraminic acid is the cytosolic sugar nucleotide pool. The Journal of Biological Chemistry 1989, 264(34):20216-20223.
13. Martínez-Maza R., Poyatos I., López-Corcuera B., et al. The role of N-glycosylation in transport to the plasma membrane and sorting of the neuronal glycine transporter glyt2. Journal of Biological Chemistry 2001, 276(3):2168-2173.
14. Hossler P., Khattak S.F., Li Z.J. Optimal and consistent protein glycosylation in mammalian cell culture. Glycobiology 2009, 19(9):936-949.
15. Balaguer E., Neusüss C. Glycoprotein characterization combining intact protein and glycan analysis by capillary electrophoresis-electrospray ionization-mass spectrometry. Analytical Chemistry 2006, 78(15):5384-5393.
16. Bateman K.P., White R.L., Yaguchi M., Thibault P. Characterization of Protein Glycoforms by Capillary-Zone Electrophoresis-Nanoelectrospray Mass Spectrometry 1998, Elsevier, Amsterdam, PAYS-BAS, p. 442.
17. Amon S., Zamfir A.D., Rizzi A. Glycosylation analysis of glycoproteins and proteoglycans using capillary electrophoresis-mass spectrometry strategies. Electrophoresis 2008, 29(12):2485-2507.
18. Kakehi K., Kinoshita M., Nakano M. Analysis of glycoproteins and the oligosaccharides thereof by high-performance capillary electrophoresis - significance in regulatory studies on biopharmaceutical products. Biomedical Chromatography 2002, 16(2):103-115.
19. Pilobello K.T., Mahal L.K. Lectin microarrays for glycoprotein analysis. Methods in Molecular Biology 2007, 385:193-203.
20. Pilobello K.T., Mahal L.K. Deciphering the glycocode: The complexity and analytical challenge of glycomics. Current Opinion in Chemical Biology 2007, 11(3):300-305.
21. Pilobello K.T., Slawek D.E., Mahal L.K. A ratiometric lectin microarray approach to analysis of the dynamic mammalian glycome. Proceedings of the National Academy of Sciences of the United States of America 2007, 104(28):11534-11539.
22. Rosenfeld R., Bangio H., Gerwig G.J., et al. A lectin array-based methodology for the analysis of protein glycosylation. Journal of Biochemical and Biophysical Methods 2007, 70(3):415-426.
23. La Belle J.T., Gerlach J.Q., Svarovsky S., Joshi L. Label-free impedimetric detection of glycan-lectin interactions. Analytical Chemistry 2007, 79(18):6959-6964.
24. Royle L., Dwek R.A., Rudd P.M. Determining the structure of oligosaccharides N- and O-linked to glycoproteins. Current Protocols in Protein Science 2006, Chapter 12: Unit 12.6.
25. Patel T., Bruce J., Merry A., et al. Use of hydrazine to release in intact and unreduced form both N- and O-linked oligosaccharides from glycoproteins. Biochemistry 1993, 32:679-693.
26. Merry A.H., Neville D.C.A., Royle L., et al. Recovery of intact 2-aminobenzamide-labeled O-glycans released from glycoproteins by hydrazinolysis. Analytical Biochemistry 2002, 304(1):91-99.
27. Deberire P., Montreuil J., Moczar E., et al. Primary structure of two major glycans of bovine fibrinogen. European Journal of Biochemistry 1985, 151(3):607-611.
28. Kuhn P., Tarentino A.L., Plummer T.H., Van Roey P. Crystal structure of peptide-N4-(N-acetyl-beta-d-glucosaminyl)asparagine amidase F at 2.2-A resolution. Biochemistry 1994, 33(39):11699-11706.
29. 4-(N-acetyl-β-glucosaminyl)asparagine amidase F cannot release glycans with fucose attached α1 → 3 to the asparagine-linked N-acetylglucosamine residue. European Journal of Biochemistry 1991, 199(3):647-652.
30. Zhao K.W., Faull K.F., Kakkis E.D., Neufeld E.F. Carbohydrate structures of recombinant human alpha-l-iduronidase secreted by Chinese hamster ovary cells. The Journal of Biological Chemistry 1997, 272(36):22758-22765.
31. Royle L., Radcliffe C.M., Dwek R.A., Rudd P.M. Detailed structural analysis of N-glycans released from glycoproteins in SDS-PAGE gel bands using HPLC combined with exoglycosidase array digestions. Methods in Molecular Biology 2006, Humana Press Inc., Totowa, NJ. I. Brockhausen (Ed.).
32. Trimble R.B., Maley F. Optimizing hydrolysis of N-linked high-mannose oligosaccharides by endo-beta-N-acetylglucosaminidase H. Analytical Biochemistry 1984, 141(2):515-522.
33. Royle L., Campbell M.P., Radcliffe C.M., et al. HPLC-based analysis of serum N-glycans on a 96-well plate platform with dedicated database software. Analytical Biochemistry 2008, 376(1):1-12.
34. Bigge J.C., Patel T.P., Bruce J.A., et al. Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Analytical Biochemistry 1995, 230(2):229-238.
35. Shilova N.V., Bovin N.V. Fluorescent labels for the analysis of mono- and oligosaccharides. Russian Journal of Bioorganic Chemistry 2002, 29(4):339-355.
36. Kamoda S., Nakano M., Ishikawa R., et al. Rapid and sensitive screening of N-glycans as 9-fluorenylmethyl derivatives by high-performance liquid chromatography: A method which can recover free oligosaccharides after analysis. Journal of Proteome Research 2005, 4(1):146-152.
37. Fernandes D. Biopharmaceutical sialylation. European Biopharmaceutical Review 2006, Spring:100-104.
38. Prater B.D., Anumula K.R., Hutchins J.T. Automated sample preparation facilitated by PhyNexus MEA purification system for oligosaccharide mapping of glycoproteins. Analytical Biochemistry 2007, 369(2):202-209.
39. Guile G.R., Rudd P.M., Wing D.R., et al. A rapid high-resolution high-performance liquid chromatographic method for separating glycan mixtures and analyzing oligosaccharide profiles. Analytical Biochemistry 1996, 240(2):210-226.
40. Campbell M.P., Royle L., Radcliffe C.M., et al. Glycobase and autogu: Tools for HPLC-based glycan analysis. Bioinformatics 2008, 24(9):1214-1216.
41. Anumula K.R. High-sensitivity and high-resolution methods for glycoprotein analysis. Analytical Biochemistry 2000, 283(1):17-26.
42. Anumula K.R. Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Analytical Biochemistry 2006, 350(1):1-23.
43. Domann P.J., Pardos-Pardos A.C., Fernandes D.L., et al. Separation-based glycoprofiling approaches using fluorescent labels. Proteomics 2007, 7(Suppl. 1):70-76.
44. Knezević A., Polasek O., Gornik O., et al. Variability, heritability and environmental determinants of human plasma N-glycome. Journal of Proteome Research 2008, 8(2):694-701.
45. Guillarme D., Grata E., Glauser G., et al. Some solutions to obtain very efficient separations in isocratic and gradient modes using small particles size and ultra-high pressure. Journal of Chromatography A 2009, 1216(15):3232-3243.
46. th Jan 2011. http://www. Chromatographyonline.com.
47. Guile G.R., Harvey D.J., O'Donnell N., et al. Identification of highly fucosylated N-linked oligosaccharides from the human parotid gland. European Journal of Biochemistry 1998, 258(2):623-656.
48. Pabst M., Bondili J.S., Stadlmann J., et al. Mass+retention time=structure: A strategy for the analysis of N-glycans by carbon LC-ESI-MS and its application to fibrin N-glycans. Analytical Chemistry 2007, 79(13):5051-5057.
49. Koizumi K. High-performance liquid chromatographic separation of carbohydrates on graphitized carbon columns. Journal of Chromatography A 1996, 720:119-126.
50. Gennaro L.A., Harvey D.J., Vouros P. Reversed-phase ion-pairing liquid chromatography/ion trap mass spectrometry for the analysis of negatively charged, derivatized glycans. Rapid Communications in Mass Spectrometry 2003, 17(14):1528-1534.
51. Chen L., Yet M., Shao M. New methods for rapid separation and detection of oligosaccharides from glycoproteins. The FASEB Journal 1988, 2(12):2819-2824.
52. Townsend R.R., Hardy M.R. Analysis of glycoprotein oligosaccharides using high-pH anion exchange chromatography. Glycobiology 1991, 1(2):139-147.
53. Kotani N., Takasaki S. Analysis of 2-aminobenzamide-labeled oligosaccharides by high-pH anion-exchange chromatography with fluorometric detection. Analytical Biochemistry 1998, 264(1):66-73.
54. Okazaki A., Shoji-Hosaka E., Nakamura K., et al. Fucose depletion from human IgG1 oligosaccharide enhances binding enthalpy and association rate between IgG1 and Fc[gamma]RIIIa. Journal of Molecular Biology 2004, 336(5):1239-1249.
55. Walsh G., Jefferis R. Post-translational modifications in the context of therapeutic proteins. Nature Biotechnology 2006, 24(10):1241-1252.
56. van de Geijn F.E., Wuhrer M., Selman M.H., et al. Immunoglobulin G galactosylation and sialylation are associated with pregnancy-induced improvement of rheumatoid arthritis and the postpartum flare: Results from a large prospective cohort study. Arthritis Research & Therapy 2009, 11(6):R193.
57. Haeuptle M.A., Hennet T. Congenital disorders of glycosylation: An update on defects affecting the biosynthesis of dolichol-linked oligosaccharides. Human Mutation 2009, 30(12):1628-1641.
58. Blow N. Glycobiology: A spoonful of sugar. Nature 2009, 457(7229):617-620.
59. Kawasaki N., Itoh S., Hashii N., et al. The significance of glycosylation analysis in development of biopharmaceuticals. Biological & Pharmaceutical Bulletin 2009, 32(5):796-800.
60. Artemenko N.V., Campbell M.P., Rudd P.M. GlycoExtractor - a web-based interface for high throughput processing of HPLC-glycan data. Journal of Proteome Research 2010, 9:2037-2041.
61. Goldberg D., Sutton-Smith M., Paulson J., Dell A. Automatic annotation of matrix-assisted laser desorption/ionization N-glycan spectra. Proteomics 2005, 5(4):865-875.
62. Ceroni A., Maass K., Geyer H., et al. GlycoWorkbench: A tool for the computer-assisted annotation of mass spectra of glycans. Journal of Proteome Research 2008, 7(4):1650-1659.
63. Maass K., Ranzinger R., Geyer H., et al. 'Glyco-peakfinder' - de novo composition analysis of glycoconjugates. Proteomics 2007, 7(24):4435-4444.
64. Loss A., Stenutz R., Schwarzer E., von der Lieth C.W. GlyNest and CASPER: Two independent approaches to estimate 1H and 13C NMR shifts of glycans available through a common web-interface. Nucleic Acids Research 2006, 34(Web Server issue):W733-W737.
65. Harvey D.J., Merry A.H., Royle L., et al. Proposal for a standard system for drawing structural diagrams of N- and O-linked carbohydrates and related compounds. Proteomics 2009, 9(15):3796-3801.
66. Ashline D.J., Lapadula A.J., Liu Y.H., et al. Carbohydrate structural isomers analyzed by sequential mass spectrometry. Analytical Chemistry 2007, 79(10):3830-3842.
67. Ashline D., Singh S., Hanneman A., Reinhold V. Congruent strategies for carbohydrate sequencing. 1. Mining structural details by MSn. Analytical Chemistry 2005, 77(19):6250-6262.
68. Sheeley D.M., Reinhold V.N. Structural characterization of carbohydrate sequence, linkage, and branching in a quadrupole ion trap mass spectrometer: Neutral oligosaccharides and N-linked glycans. Analytical Chemistry 1998, 70(14):3053-3059.
69. Prien J.M., Huysentruyt L.C., Ashline D.J., et al. Differentiating N-linked glycan structural isomers in metastatic and nonmetastatic tumor cells using sequential mass spectrometry. Glycobiology 2008, 18(5):353-366.
70. Hanneman A.J., Rosa J.C., Ashline D., Reinhold V.N. Isomer and glycomer complexities of core GlcNAcs in Caenorhabditis elegans. Glycobiology 2006, 16(9):874-890.
71. Prien J.M., Ashline D.J., Lapadula A.J., et al. The high mannose glycans from bovine ribonuclease B isomer characterization by ion trap MS. Journal of the American Society for Mass Spectrometry 2009, 20(4):539-556.
72. Zaia J. Mass spectrometry and the emerging field of glycomics. Chemistry & Biology 2008, 15(9):881-892.
73. Harvey D.J. Fragmentation of negative ions from carbohydrates: Part 2, fragmentation of high-mannose N-linked glycans. Journal of the American Society for Mass Spectrometry 2005, 16:631-646.
74. Harvey D.J. Fragmentation of negative ions from carbohydrates: Part 1. Use of nitrate and other anionic adducts for the production of negative ion electrospray spectra from N-linked carbohydrates. Journal of the American Society for Mass Spectrometry 2005, 16:622-630.
75. Harvey D.J. Fragmentation of negative ions from carbohydrates: Part 3. Fragmentation of hybrid and complex N-linked glycans. Journal of the American Society for Mass Spectrometry 2005, 16:647-659.
76. Domon B., Costello C.E. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate Journal 1988, 5:397-409.
77. Guttman A. High-resolution carbohydrate profiling by capillary gel electrophoresis. Nature 1996, 380(6573):461-462.
78. Callewaert N., Contreras R., Mitnik-Gankin L., et al. Total serum protein N-glycome profiling on a capillary electrophoresis-microfluidics platform. Electrophoresis 2004, 25(18-19):3128-3131.
79. Khandurina J., Anderson A.A., Olson N.A., et al. Large-scale carbohydrate analysis by capillary array electrophoresis: Part 2. Data normalization and quantification. Electrophoresis 2004, 25(18-19):3122-3127.
80. Khandurina J., Blum D.L., Stege J.T., Guttman A. Automated carbohydrate profiling by capillary electrophoresis: A bioindustrial approach. Electrophoresis 2004, 25(14):2326-2331.
81. Olajos M., Hajăłs P., Bonn G.K., Guttman A. Sample preparation for the analysis of complex carbohydrates by multicapillary gel electrophoresis with light-emitting diode induced fluorescence detection. Analytical Chemistry 2008, 80(11):4241-4246.
82. Edge C.J., Rademacher T.W., Wormald M.R., et al. Fast sequencing of oligosaccharides: The reagent-array analysis method. Proceedings of the National Academy of Sciences of the United States of America 1992, 89(14):6338-6342.
83. Guttman A., Ulfelder K.W. Exoglycosidase matrix-mediated sequencing of a complex glycan pool by capillary electrophoresis. Journal of Chromatography A 1997, 781(1-2):547-554.
84. Fan J.Q., Namiki Y., Matsuoka K., Lee Y.C. Comparison of acid hydrolytic conditions for Asn-linked oligosaccharides. Analytical Biochemistry 1994, 219(2):375-378.
85. Hardy M.R., Townsend R.R., Lee Y.C. Monosaccharide analysis of glycoconjugates by anion exchange chromatography with pulsed amperometric detection. Analytical Biochemistry 1988, 170(1):54-62.
86. Higa H.H., Paulson J.C. Sialylation of glycoprotein oligosaccharides with N-acetyl-, N-glycolyl-, and N-O-diacetylneuraminic acids. Journal of Biological Chemistry 1985, 260(15):8838-8849.
87. Baker K.N., Rendall M.H., Hills A.E., et al. Metabolic control of recombinant protein N-glycan processing in NS0 and CHO cells. Biotechnology and Bioengineering 2001, 73(3):188-202.