Protein Glycosylation: The Basic Science

Post-translational Modification of Protein Biopharmaceuticals

Volumn , Issue , 2009, Pages 15-49

  Brooks, Susan A ^a  

^a OXFORD BROOKES UNIVERSITY   (United Kingdom)

Author keywords

Core structures; Glycans; Glycosylation; Monosaccharides; Polysaccharides

Indexed keywords

EID: 84889326192     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527626601.ch2     Document Type: Chapter

References (143)

1. Dwek, R.A. (1996) Glycobiology: toward the understanding of the function of sugars. Chemical Reviews, 96, 683-720.
2. Rudd, P.M. and Dwek, R.A. (1991) Glycobiology: a coming of age. Chemistry & Industry, 2, 660-663.
3. Rudd, P.M. (1993) Oligosaccharides in human biology. Glyco News, 3, 1-8.
4. Fukuda, M. (1994) Cell surface carbohydrates: cell-type specific expression, in Molecular Glycobiology (eds M. Fukuda and O. Hindsgaul), IRL Press, Ch 1, pp. 1-52.
5. Taylor, M.E. and Drickamer, K. (2006) Glycosylation and disease, in Introduction to Glycobiology, 2nd edn, Oxford University Press, Ch 12, pp. 218-235.
6. Varki, A. et al. (1999) Historical background and overview, in Essentials of Glycobiology, Cold Harbor Laboratory Press, New York, Ch 1, pp. 1-16.
7. Brooks, S.A. (2004) Appropriate glycosylation of recombinant proteins for human use: implications of choice of expression system. Molecular Biotechnology, 28, 241-256.
8. Brooks, S.A. (2006) Protein glycosylation in diverse cell systems: implications for modification and analysis of recombinant proteins. Expert Review of Proteomics, 3, 345-359.
9. Brooks, S.A., Dwek, M.V. and Schumacher, U. (2002) Carbohydrate biotechnology, in Functional and Molecular Glycobiology, Bios Scientific Publishers, Ltd, Oxford, UK, Ch 18, pp. 329-345.
10. Apweiler, R., Hermjakob, H. and Sharon, N. (1999) On the frequency of protein glycosylation as deduced from analysis of the SWISS-PROT database. Biochimica et Biophysica Acta, 1473, 4-8.
11. Hagglund, P. et al. (2004) A new strategy for identification of I-glycosylated proteins and unambiguous assignment of their glycosylation sites using HILIC enrichment and partial deglycosylation. Journal of Proteome Research, 3, 556-566.
12. Kameyama, A. et al. (2006) Strategy for simulation of CID spectra of N-linked oligosaccharids towards glycomics. Journal of Proteome Research, 5, 808-814.
13. Rademacher, T.W., Parekh, R.B. and Dwek, R.A. (1998) Glycobiology. Annual Review of Biochemistry, 57, 785-838.
14. Delves, P.J. (1998) The role of glycosylation in autoimmune disease. Autoimmunity, 27, 239-253.
15. Haltiwanger, R.S. and Lowe, J.B. (2004) Role of glycosylation in development. Annual Review of Biochemistry, 73, 491-537.
16. Ohtsubo, K. and Marth, J.D. (2006) Glycosylation in cellular mechanisms of health and disease. Cell, 126, 855-867.
17. Rudd, P.M., Wormald, M.R. and Dwek, R.A. (2004) Sugar-mediated interactions in the immune system. Trends in Biotechnology, 22, 524-530.
18. Roseman, S. (2001) Reflections on glycobiology. The Journal of Biological Chemistry, 276, 41527-41542.
19. Brooks, S.A., Dwek, M.V. and Schumacher, U. (2002) Disease processes in which carbohydrates are involved, in Functional and Molecular Glycobiology, Bios Scientific Publishers, Ltd, Oxford, UK, Ch 16, pp. 287-312.
20. Dennis, J.W. (1992) Oligosaccharides in carcinogenesis and metastasis. Glyco News, 2, 1-4.
21. Dall'Olio, F. (1996) Protein glycosylation in cancer biology: an overview. Journal of Clinical Pathology, 49, M126-M135.
22. Fukuda, M. (1996) Possible roles of tumour associated carbohydrate antigens. Cancer Research, 56, 2237-2244.
23. Ho, S.B. and Kim, Y.S. (1997) Glycoproteins and glycosylation changes in cancer, in Encyclopaedia of Cancer, Vol II, Academic Press, pp. 744-759.
24. Kannagi, R. (1997) Carbohydratemediated cell adhesion involved in hematogenous metastasis of cancer. Glycoconjugate Journal, 14, 577-584.
25. Kim, Y.J. andVarki, A. (1997) Perspectives on the significance of altered glycosylation of glycoproteins in cancer. Glycoconjugate Journal, 14, 569-576.
26. Price, J.T., Bonovich, M.T. and Kohn, E.C. (1997) The biochemistry of cancer dissemination. Critical Reviews in Biochemistry and Molecular Biology, 32, 175-253.
27. Dube, D.H. and Bertozzi, C.R. (2005) Glycans in cancer and inflammation - potential for therapeutics and diagnostics. Nature Reviews. Drug Discovery, 4, 477-488.
28. Varki, A. et al. (1999) Saccharide structure and nomenclature, in Essentials of Glycobiology, Cold Harbor Laboratory Press, New York, Ch 2, pp. 17-30.
29. Brooks, S.A., Dwek, M.V. and Schumacher, U. (2002) An introduction to carbohydrate chemistry, in Functional and Molecular Glycobiology, Bios Scientific Publishers, Ltd, Oxford, UK, Ch 1, pp. 1-30.
30. Van den Eijnden, D.H. and Joziasse, D.H. (1993) Enzymes associated with glycosylation. Current Opinion in Structural Biology, 3, 711-721.
31. Ten Hagen, K.G., Fritz, T.A. and Tabak, L.A. (2003) All the family: the UDP:GalNAc:polypeptide N-acetylgalactosaminyltransferases. Glycobiology, 13, 1R-16.
32. Kleene, R. and Berger, E.G. (1993) The molecular and cell biology of glycosyltransferases. Biochimica et Biophysica Acta, 1154, 283-325.
33. Brockhausen, I. and Schachter, H. (1997) Glycosyltransferases involved in N- and O-glycan synthesis, in Glycosciences - Status and Perspectives (eds H.-J. Gabius and S. Gabius), Chapman and Hall, Weinheim, Ch 5, pp. 79-111.
34. Joziasse, D.H. (1992) Mammalian glycosyltranferases: genomic organisation and protein structure. Glycobiology, 9, 271-277.
35. Drickamer, K. and Taylor, M.E. (1998) Evolving views of protein glycosylation. Trends in Biochemical Sciences, 23, 321-324.
36. Cornelli, E.M. et al. (2006) A focussed microarray approach to functional glycomics: transcriptional regulation for the glycome. Glycobiology, 16, 117-131.
37. Bretscher, M.S. and Munro, S. (1993) Cholesterol and the Golgi apparatus. Science, 261, 1280-1281.
38. Masibay, A.S. et al. (1993) Mutational analysis of the Golgi retention signal of bovine β-1,4-galactosyltransferase. The Journal of Biological Chemistry, 268, 9908-9916.
39. Machamer, C.E. (1991) Golgi retention signals: do membranes hold the key? Trends in Cell Biology, 1, 141-144.
40. Nilsson, I.M. and von Heijne, G. (1993) Determination of the distance between the oligosaccharyltransferase active site and the endoplasmic reticulum membrane. The Journal of Biological Chemistry, 268, 5798-5801.
41. Schachter, H. (2000) The joys of HexNAc. The synthesis and function of N- and O-glycan branches. Glycoconjugate Journal, 17, 465-483.
42. Varki, A. et al. (1999) N-glycans, in Essentials of Glycobiology, Cold Harbor Laboratory Press, New York, Ch 7, pp. 85-100.
43. Varki, A. et al. (1999) O-glycans, in Essentials of Glycobiology, Cold Harbor Laboratory Press, New York, Ch 8, pp. 101-114.
44. Brooks, S.A., Dwek, M.V. and Schumacher, U. (2002) N-linked glycoproteins, in Functional and Molecular Glycobiology, Bios Scientific Publishers, Ltd, Oxford, UK, Ch 4, pp. 73-88.
45. Brooks, S.A., Dwek, M.V. and Schumacher, U. (2002) O-linked (mucintype) glycoproteins, in Functional and Molecular Glycobiology, Bios Scientific Publishers, Ltd, Oxford, UK, Ch 5, pp. 89-115.
46. Brooks, S.A. et al. (2008) Altered glycosylation of proteins in cancer: what is the potential for new anti-tumour strategies? Anti-Cancer Agents in Medicinal Chemistry, 8, 2-21.
47. Yan, A. and Lennarz, W.J. (2005) Unraveling the mechanism of protein N-glycosylation. The Journal of Biological Chemistry, 280, 3121-3124.
48. Hirschberg, C.B. and Snider, M.D. (1987) Topology of glycosylation in the rough endoplasmic reticulum and Golgi apparatus. Annual Review of Biochemistry, 56, 63-87.
49. Helenius, J. and Aebi, M. (2002) Transmembrane movement of dolichol linked carbohydrates during N-glycoprotein biosynthesis in the endoplasmic reticulum. Cell & Developmental Biology, 13, 171-178.
50. Sears, P. and Wong, C.H. (1998) Enzyme action in glycoprotein synthesis. Cellular and Molecular Life Sciences, 54, 223-252.
51. Dempski, R.E. Jr, and Imperiali, B. (2002) Oligosaccharyl transferase: gatekeeper to the secretory pathway. Current Opinion in Chemical Biology, 6, 844-850.
52. Parodi, A.J. (2000) Protein glucosylation and its role in protein folding. Annual Review of Biochemistry, 69, 69-93.
53. Ito, Y. et al. (2005) Structural approaches to the study of oligosaccharides in glycoprotein quality control. Current Opinion in Structural Biology, 15, 481-489.
54. Petrescu, A.J. et al. (2004) Statistical analysis of the protein environment of N-glycosylation sites: implications for occupancy, structure and folding. Glycobiology, 14, 103-114.
55. Hanisch, F.-G. (2001) O-glycosylation of the mucin type. Biological Chemistry, 382, 143-149.
56. Haltiwanger, R.S. et al. (1992) Glycosylation of nuclear and cytoplasmic proteins is ubiquitous and dynamic. Biochemical Society Transactions, 20, 264-269.
57. Hart, G.W. (1997) Dynamic O-linked glycosylation of nuclear and cytoskeletal proteins. Annual Review of Biochemistry, 66, 315-335.
58. Nishimura, H. et al. (1992) Human factor IX has a tetrasaccharide O-glycosidically linked to serine 61 through the fucose residue. The Journal of Biological Chemistry, 267, 17520-17525.
59. Harris, R.J. et al. (1991) Tissue plasminogen activator has an O-linked fucose attached to threonine-61 in the epidermal growth factor domain. Biochemistry, 30, 2311-2314.
60. Kieliszewski, M.J. et al. (1995) Tandem mass spectrometry and structural elucidation of glycopeptides from a hydroxyproline-rich plant cell wall glycoprotein indicate that contiguous hydroxyproline residues are the major sites of hydoxyproline O-arabinosylation. The Journal of Biological Chemistry, 270, 2541-2549.
61. Duman,J.G. et al. (1998) O-Mannosylation of Pichia pastoris cellular and recombinant proteins. Biotechnology and Applied Biochemistry, 28, 39-45.
62. Brockhausen, I. (1995) Biosynthesis of O-glycans of the N-acetylgalactosaminea-Ser/Thr linkage type, in Glycoproteins (eds J. Montreuil, H. Schacter and J.F.G. Vliegenthart), Elsevier Science BV, Amsterdam, Ch 5, pp. 201-259.
63. Dekker, J. et al. (2002) Review: the MUC family - an obituary. Trends in Biochemical Sciences, 27, 126-131.
64. Van den Steen, P. et al. (1998) Concepts and principles of O-linked glycosylation. Critical Reviews in Biochemistry and Molecular Biology, 33, 151-208.
65. Brockhausen, I. et al. (1996) Specificity of O-glycosylation by bovine colostrums UDP-GalNAc: polypeptide alpha-N-acetylgalactosaminyltransferase using synthetic glycopeptide substrates. Glycoconjugate Journal, 13, 849-856.
66. Hansen, J.E. et al. (1995) Prediction of O-glycosylation of mammalian proteins: specificity patterns of UDPGalNAc: poly- peptide Nacetylgalactosaminyltransferase. The Biochemical Journal, 308, 801-813.
67. Hansen, J.E. et al. (1998) NetOglyc: prediction of mucin type O-glycosylation sites based on sequence context and surface accessibility. Glycoconjugate Journal, 15, 115-130.
68. Gupta, R. et al. (1999) O-GLYCBASE version 4.0: a revised database of O-glycosylated proteins. Nucleic Acids Research, 27, 370-372.
69. Thanka Christlet, T.H. and Veluraja, K. (2001) Database analysis of O-glycosylation sites in proteins. Biophysical Journal, 80, 952-960.
70. Julienus, K. et al. (2005) Prediction, conservation analysis, and structural characterisation of mammalian mucintype O-glycosylation sites. Glycobiology, 15, 153-164.
71. Pavelka, M. (1997) Topology of glycosylation - a histochemist's view, in Glycosciences - Status and Perspectives, (eds H-.J. Gabius and S. Gabius), Chapman and Hall, Weinheim, Ch 6, pp. 115-120.
72. Springer, G.F. (1984) T and Tn, general carcinoma auto-antigens. Science, 224, 1198-1206.
73. Springer, G.F. (1989) Tn epitope (N-acetylgalactosamine a-O-serine/threonine) density in primary breast carcinoma: a functional predictor of aggressiveness. Molecular Immunology, 26, 1-5.
74. Ibrahim, N.K. and Murray, J.L. (2003) Clinical development of the STn-KLH vaccine (Theratope). Clinical Breast Cancer, 3 (Suppl. 4), S139-S143.
75. Holmberg, L.A. and Sandmaier, B.M. (2004) Vaccination with Theratope (STn-KLH) as treatment for breast cancer. Expert Review of Vaccines, 3, 655-663.
76. Hakomori, S. (2002) Glycosylation defining malignancy: new wine in an old bottle. Proceedings of the National Academy of Sciences of the United States of America, 99, 10231-10233.
77. Kobata, A. and Amano, J. (2005) Latered glycosylation of proteins produced by malignant cells, and applications in the diagnosis and immunotherapy of tumors. Immunology and Cell Biology, 83, 429-439.
78. Brooks, S.A., Dwek, M.V. and Schumacher, U. (2002) Glycan chain extension and some common and important glycan structures, in Functional and Molecular Glycobiology, Bios Scientific Publishers, Ltd, Oxford, UK, Ch 10, pp. 187-202.
79. Dwek, R.A. et al. (1993) Analysis of glycoprotein-associated oligosaccharides. Annual Review of Biochemistry, 62, 65-100.
80. Rudd, P.M. et al. (1997) Oligosaccharide sequencing technology. Nature, 388, 205-207.
81. Rudd, P.M. and Dwek, R.A. (1997) Rapid, sensitive sequencing of oligosaccharides from glycoproteins. Current Opinion in Biotechnology, 8, 488-497.
82. Anumula, K.R. (2000) High-sensitivity and high-resolution methods for glycoprotein analysis. Analytical Biochemistry, 283, 17-26.
83. Wuhrer, M., Deelder, A.M. and Hokke, C.H. (2005) Protein glycosylation analysis by liquid chromatography - mass spectrometry. Journal of Chromatography B, 825, 124-133.
84. Geyer, H. and Geyer, R. (2006) Strategies for analysis of glycosylation. Biochim Biophys Acta - Proteins and Proteomics, 1764, 1853-1869.
85. Mechref, Y. and Novotny, M.V. (2006) Miniturized separation techniques in glycomic investigations. Journal of Chromatography B, 841, 65-78.
86. Pilobello, K.T. and Mahal, L.K. (2007) Deciphering the glycocode: the complexity and analytical challenge of glycomics. Current Opinion in Chemical Biology, 11, 300-305.
87. Raman, R. et al. (2005) Glycomics: an integrated systems approach to structurefunction relationships of glycans. Nature Methods, 2, 817-824.
88. Mamitsuka, H. (2007) Informatic innovations in glycobiology: relevance to drug discovery. Drug Discovery Today, 13, 118-123.
89. Patton, W.F. (2002) Fluorescence detection of glycoproteins in gels and on electroblots. Current Protocols in Cell Biology, John Wiley & Sons, Chapter 6, Unit 6.8.
90. Rudiger, H. and Gabius, H.J. (2001) Plant lectins: occurrence, biochemistry, functions and applications. Glycoconjugate Journal, 18, 589-613.
91. Sharon, N. and Lis, H. (2004) History of lectins: from hemagglutinins to biological recognition molecules. Glycobiology, 14, 53-62.
92. Schumacher, U., Brooks, S.A. and Leathem, A.J. (1991) Lectins as tools in histochemical techniques: a review of methodological aspects, in Lectin Reviews, Vol 1 (eds D.C. Kilpatrick, E. Van Driessche and T.C. Bog-Hansen), Sigma Chemical Company, St Louis, MO, USA, pp. 195-201.
93. Brooks, S.A., Leathem, A.J.C. and Schumacher, U. (1997) Lectin Histochemistry - A Concise Practical Handbook, Bios Scientific Publishers, Oxford, UK.
94. Brooks, S.A. and Hall, D.M.S. (2001) Lectin histochemistry to detect altered glycosylation in cells and tissues, in Metastasis Research Protocols, Vol I: Analysis of Cells and Tissues (eds S.A. Brooks and U. Schumacher), Humana Press, Ch 4, pp. 49-66.
95. Carter, T.M. and Brooks, S.A. (2006) Detection of aberrant glycosylation in breast cancer using lectin histochemistry, in Breast Cancer Research Protocols (eds S.A. Brooks and A. Harris), Humana Press, Ch 16, pp. 201-216.
96. Cataldi, T.R., Campa, C. and De Benedetto, G.E. (2000) Carbohydrate analysis by high-performance anionexchange chromatography with pulsed amperometric detection: the potential is still growing. Fresenius? Journal of Analytical Chemistry, 368, 739-758.
97. Rohrer, J.S. (2000) Analyzing sialic acids using high-performance anion-exchange chromatography with pulsed amperometric detection. Analytical Biochemistry, 283, 3-9.
98. Bigge, J.C. et al. (1995) Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Analytical Biochemistry, 230, 229-238.
99. Zhuang, Z. et al. (2007) Electrophoretic analysis of N-glycans on microfluidic devices. Analytical Chemistry, 79, 7170-7175.
100. Anumula, K.R. (2008) Unique anthranilic acid chemistry facilitates profiling and characterization of Ser/Thr-linked sugar chains following hydrazinolysis. Analytical Biochemistry, 373, 104-111.
101. Xia, B. et al. (2005) Versatile fluorescent derivatization of glycans for glycomic analysis. Nature Methods, 2, 845-850.
102. Hirabayshi, J. (2004) Lectin-based structural glycomics: glycoproteomics and glycan profiling. Glycoconjugate Journal, 21, 35-40.
103. Pilobello, K.T. et al. (2005) Development of a lectin microarray for the rapid analysis of protein glycopatterns. ChemBioChem, 6, 985-989.
104. Hsu, K.L., Pilobello, K.T. and Mahal, L.K. (2006) Analyzing the dynamic bacterial glycome with a lectin microarray approach. Nature Chemical Biology, 2, 153-157.
105. Hsu, K.L. and Mahal, L.K. (2006) A lectin microarray approach for the rapid analysis of bacterial glycans. Nature Protocols, 1, 543-549.
106. Manimala, J.C. et al. (2005) Carbohydrate array analysis of anti-Tn antibodies and lectins reveals unexpected specificities: implications for diagnostic and vaccine development. Chem Bio Chem, 6, 2229-2241.
107. Osborne, C. and Brooks, S.A. (2006) SDS-PAGE andWestern blotting to detect proteins and glycoproteins of interest in breast cancer research, in Breast Cancer Research Protocols (eds S.A. Brooks and A. Harris), Humana Press, Ch 17, pp. 217-230.
108. Wilson, N.L. et al. (2002) Sequential analysis of N- and O-linked glycosylation of 2D-PAGE separated glycoproteins. Journal of Proteome Research, 1, 521-529.
109. Dwek, M.V. and Rawlings, S.L. (2002) Current perspectives in cancer proteomics. Molecular Biotechnology, 22, 139-152.
110. Dwek, M.V. and Rawlings, S.L. (2006) Breast cancer proteomics using twodimensional electrophoresis: studying the breast cancer proteome, in Breast Cancer Research Protocols (eds S.A. Brooks and A. Harris), Humana Press, Ch 18, pp. 231-244.
111. Dwek, M.V. and Alaiya, A.A. (2003) Proteome analysis enables separate clustering of normal breast, benign breast and breast cancer tissues. British Journal of Cancer, 89, 305-307.
112. Block, T.M. et al. (2005) Use of targeted glycoproteomics to identify serum glycoproteins that correlate with liver cancer in woodchucks and humans. Proceedings of the National Academy of Sciences of the United States of America, 102, 779-784.
113. Rudd, P.M. et al. (2001) A highperformance liquid chromatography based strategy for rapid, sensitive sequencing of N-linked oligosaccharide modifications to proteins in sodium dodecyl sulphate polyacrylamide electrophoresis gel bands. Proteomics, 1, 285-294.
114. Royle, L. et al. (2006) 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 (Clifton, NJ), 347, 125-143.
115. Manzi, A.E. (2001) Total compositional analysis by high-performance liquid chromatography or gas-liquid chromatography. Current Protocols in Molecular Biology, John Wiley & Sons, Chapter 17, Unit17, 19A.
116. Patel, T.P. and Parekh, R.B. (1994) Release of oligosaccharides from glycoproteins by hydrazinolysis. Methods in Enzymology, 230, 57-66.
117. Freeze, H.H., Varki, A. and Endoglycosidase, F. (1986) peptide N-glycosidase F release the great majority of total cellular N-linked oligosaccharides: use in demonstrating that sulfated N-linked oligosaccharides are frequently found in cultured cells. Biochemical and Biophysical Research Communications, 140, 967-973.
118. Kuster, B. et al. (1998) Structural determination of N-linked carbohydrates by matrix-assisted laser desorption/ionization-mass spectrometry following enzymatic release within sodium dodecyl sulphate-polyacrylamide electrophoresis gels: application to species-specific glycosylation of alpha1-acid glycoprotein. Electrophoresis, 19, 1950-1959.
119. Royle, L. et al. (2008) HPLC-based analysis of serum N-glycans on a 96-well plate platformwith dedicated database software. Analytical Biochemistry, 376, 1-12.
120. Guile, G.R.,Wong, S.Y.C. and Dwek, R.A. (1994) Analytical and preparative separation of anionic oligosaccharides by weak anion exchange high performance liquid chromatography on an inert polymer column. Analytical Biochemistry, 222, 231-235.
121. Lee, Y.C. (1990) Review: high performance anion-exchange chromatography for carbohydrate analysis. Analytical Biochemistry, 189, 151-162.
122. Lee, Y.C. (1996) Review: carbohydrate analyses with high performance anionexchange chromatography. Journal of Chromatography. A, 720, 137-149.
123. Nakano, M., Kakehi, K. and Lee, Y.C. (2003) Sample clean-up method for analysis of complex N-glycans released from glycopeptides. Journal of Chromatography A, 1005, 13-21.
124. Jackson, P. (1991) Polyacrylamide gel electrophoresis of reducing saccharides labelled with the fluorophore 2-aminoacridone: subpicomolar detection using an imaging system based on a cooled charge-coupled device. Analytical Biochemistry, 196, 238-244.
125. Nakajima, K. et al. (2003) Capillary affinity electrophoresis for the screening of posttranslational modification of protein with carbohydrates. Journal of Proteome Research, 2, 81-88.
126. Shimaoka, H. et al. (2007) One-pot solidphase glycoblotting and probing by transoximization for high-throuput glycomics and glycoproteomics. Chemistry (Weinheim an der Bergstrasse, Germany), 13, 1664-1673.
127. Lohse, A. et al. (2006) Solid phase oligosaccharide tagginf (SPOT): validation on glycolipid-derived structures. Angewandte Chemie, International Edition, 45, 4167-4172.
128. Uematsu, R. et al. (2005)High throughput quantitative glycomics and glycoformfocused proteomics of murine dermis and epidenrmis. Molecular & Cellular Proteomics, 4, 1977-1989.
129. Budnik, B.A., Lee, R.S. and Steen, J.A.J. (2006) Global methods for protein glycosylation analysis by mass spectrometry. Biochim Biophys Acta - Proteins and Proteomics, 1764, 1870-1880.
130. Jang-Jee, J. et al. (2006) Glycomic profiling of cells and tissues by mass spectrometry: fingerprinting and sequencing methodologies. Methods in Enzymology, 415, 59-86.
131. Morelle, W. and Michalski, J.C. (2005) Glycomics and mass spectrometry. Current Pharmaceutical Design, 11, 2615-2645.
132. Morelle, W. and Michalski, J.C. (2007) Analysis of protein glycosylation by mass spectrometry. Nature Protocols, 2, 1585-1602.
133. Joshi, H.J. et al. (2004) Development of a mass fingerprinting tool for automated interpretation of oligosaccharide fragmentation data. Proteomics, 4, 1640-1664.
134. Lohmann, K.K. and von der Leith, C.W. (2004) GlycoFragment and GlycoSearchMS: two tools to support the interpretation of mass spectra of complex carbohydrates. Nucleic Acids Research, 32, W261-W266.
135. Goldberg, D. et al. (2005) Automatic determination of O-glycan structure form fragmentation spectra. Journal of Proteome Research, 5, 1429-1434.
136. von der Leith, C.W., Lutteke, T. and Frank, M. (2006) The role of informatics in glycobiology research with special emphasis on automatic interpretation of MS spectra. Biochimica et Biophysica Acta, 1760, 568-577.
137. Karas, M. and Hillenkamp, F. (1988) Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons. Analytical Chemistry, 60, 2299-2301.
138. Wada, Y. et al. (1994) Diagnosis of carbohydrate-deficient glycoprotein syndrome by matrix-assisted laser desorption time-of-flight mass spectrometry. Biological Mass Spectrometry, 23, 108-109.
139. Fenn, J.B. et al. (1989) Electrospray ionization for mass spectrometry of large biomolecules. Science, 246, 64-71.
140. Harvey, D.J. (1999) Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. Mass Spectrometry Reviews, 18, 349-450.
141. Dell, A. and Morris, H.R. (2001) Glycoprotein structure determination by massspectrometry. Science, 291, 2351-2356.
142. Park, Y. and Lebrilla, C.B. (2005) Application of Fourier transform ion cyclotron resonance mass spectrometry to oligosaccharides. Mass Spectrometry Reviews, 24, 232-264.
143. Harvey, D.J. et al. (2008) Structural and quantitative analysis of N-linked glycans by matrix-assisted laser desorption ionization and negative ion nanospray mass spectrometry. Analytical Biochemistry, 376, 44-60.