Glycomics and mass spectrometry

Current Pharmaceutical Design

Volumn 11, Issue 20, 2005, Pages 2615-2645

  Morelle, Willy ^a   Michalski, Jean Claude ^a  

^a UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GENE PRODUCT; GLYCAN; GLYCOPROTEIN; OLIGOSACCHARIDE;

CELL INTERACTION; EXTRACELLULAR MATRIX; GENE FUNCTION; GLYCOBIOLOGY; GLYCOSYLATION; MASS SPECTROMETRY; METHODOLOGY; MOLECULAR RECOGNITION; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN PROCESSING; PROTEOMICS; REVIEW; STRUCTURE ANALYSIS;

ANIMALS; GLYCOPROTEINS; GLYCOSYLATION; HUMANS; MASS SPECTROMETRY; POLYSACCHARIDES; PROTEOMICS; REPRODUCIBILITY OF RESULTS; TERMINOLOGY;

EID: 22944491144     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/1381612054546897     Document Type: Review

References (310)

1. Hirabayashi J, Kasai KI. Glycomics, coming of age! Trends Glycosci Glycotechnol 2000; 12: 1-5.
2. Feizi T, Mulloy B. Carbohydrates and glycoconjugates. Glycomics: the new era of carbohydrate biology. Curr Opin Struct Biol. 2003; 13: 602-4.
3. Perkel JM. Ribozymes: Hearkening Back to an RNA World. Scientist 2002; 16: 32.
4. Moens S, Vanderleyden J. Glycoproteins in prokaryotes. Arch Microbiol 1997; 168: 169-75.
5. Hounsell EF, Davies MJ, Renouf DV. O-linked protein glycosylation structure and function. Glycoconjugate J 1996; 13: 19-26.
6. Hart GW, Haltiwanger RS, Holt GDA, Kelly WG. Glycosylation in the nucleus and cytoplasm. Annu Rev Biochem 1989; 58: 841-74.
7. Lefebvre T, Caillet-Boudin ML, Buée L, Delacourte A, Michalski JC. O-GlcNAc glycosylation and neurological disorders. Adv Exp Med Biol 2003; 535: 189-202.
8. Chai W, Yuen CT, Kogelberg H, Carruthers RA, Margolis RU, Feizi T, et al. High prevalence of 2-mono- and 2, 6-di-substituted manol-terminating sequences among O-glycans released from brain glycopeptides by reductive alkaline hydrolysis. Eur J Biochem 1999; 263: 879-88.
9. Smalheiser NR, Haslam SM, Sutton-Smith M, Morris HR, Dell A. Structural analysis of sequences O-linked to mannose reveals a novel Lewis X structure in cranin (dystroglycan) purified from sheep brain. J Biol Chem 1998; 273: 23698-703.
10. Laine RA. Information capacity of the carbohydrate code. Pure Appl Chem (Washington DC) 1997; 69: 1867-73.
11. 12 Structures for a Reducing Hexasaccharide: The Isomer Barrier to Development of Single-Method Saccharide Sequencing or Synthesis Systems. Glycobiology 1994; 6: 759-67.
12. Reinhold VN, Reinhold BB, Costello CE. Carbohydrate molecular weight profiling, sequence, linkage, and branching data: ES-MS and CID. Anal Chem 1995; 67: 1772-84.
13. Weiskopf AS, Vouros P, Harvey DJ. Characterisation of oligosaccharide composition and structure by quadrupole ion trap mass spectrometry. Rapid Commun Mass Spectrom 1997; 11: 1493-504.
14. Weiskopf AS, Vouros P, Harvey DJ. Electrospray ionisation-ion trap mass spectrometry for structural analysis of complex N-linked glycoprotein oligosaccharides. Anal Chem 1998; 70: 4441-7.
15. Morelle W, Lemoine J, Strecker G. Structural analysis of O-linked oligosaccharide-alditols by electrospray-tandem mass spectrometry after mild periodate oxidation and derivatisation with 2-aminopyridine. Anal Biochem 1998; 259: 16-27.
16. Harvey DJ. Electrospray mass spectrometry and fragmentation of N-linked carbohydrates derivatised at the reducing terminus. J Am Soc Mass Spectrom 2000; 11: 900-15.
17. Li DT, Her GR. Structural analysis of chromophore-labelled disaccharides and oligosaccharides by electrospray ionisation mass spectrometry and high-performance liquid chromatography/electrospray ionisation mass spectrometry. J Mass Spectrom 1998; 33: 644-52.
18. Mo W, Takao T, Sakamoto H, Shimonishi Y. Structural analysis of oligosaccharides derivatised with 4-aminobenzoic acid 2-(diethylamino)ethyl ester by matrix-assisted laser desorption/ionisation mass spectrometry. Anal Chem 1998; 70: 4520-6.
19. Sutton CW, O'Neill JA, Cottrell JS. Site-specific characterisation of glycoprotein carbohydrates by exoglycosidase digestion and laser desorption mass spectrometry. Anal Biochem 1994; 218: 34-46.
20. Yang Y, Orlando R. Simplifying the exoglycosidase digestion/MALDI-MS procedures for sequencing N-linked carbohydrate side chains. Anal Chem 1996; 68: 570-2.
21. Harvey DJ. Identification of cleaved oligosaccharides by matrix-assisted laser desorption/ionisation. Methods Mol Biol 1996; 61: 243-53.
22. Geyer H, Schmitt S, Wuhrer M, Geyer R. Structural analysis of glycoconjugates by on-target enzymatic digestion and MALDI-TOF-MS. Anal Chem 1999; 71: 476-82.
23. Harvey DJ. Matrix-assisted laser desorption/ionisation mass spectrometry of oligosaccharides and glycoconjugates. J Chromatogr A 1996; 720: 429-46.
24. Harvey DJ. Matrix-assisted laser desorption/ionisation mass spectrometry of carbohydrates. Mass Spectrom Rev 1999; 18: 349-450.
25. Packer NH, Harrison MJ. Glycobiology and proteomics: is mass spectrometry the Holy Grail? Electrophoresis 1998; 19: 1872-82.
26. Dell A, Morris HR. Glycoprotein structure determination by mass spectrometry. Science 2001; 291: 2351-6.
27. Mechref Y, Novotny MV. Structural investigations of glycoconjugates at high sensitivity. Chem Rev 2002; 102: 321-69.
28. Dell A. F.A.B.-mass spectrometry of carbohydrates. Adv Carbohydr Chem Biochem 1987; 45: 19-72.
29. Stahl B, Steup M, Karas M, Hillenkamp F. Analysis of neutral oligosaccharides by matrix-assisted laser desorption ionisation mass spectrometry. Anal Chem 1991; 63: 1463-66.
30. Whittal RM, Palcic MM, Hindgaul O, Li L. Direct analysis of enzymic reactions of oligosaccharides in human serum using matrix-assisted laser desorption ionisation mass spectrometry. Anal Chem 1995; 67: 3509-14.
31. Yamashita M, Fenn JB. Electrospray Ion Source. Another Variation on the Free-Jet Theme. J Chem Phys 1984; 88; 4451-59.
32. Barber RS, Bordoli RD, Sedgwick RD, Tyler AN. A FAB gun described and introduced; no matrix; several types of small polar molecules analysed. J Chem Soc Chem Commun 1981; 325-27.
33. Dell A. Preparation and desorption mass spectrometry of permethyl and peracetyl derivatives of oligosaccharides. In: Methods in Enzymology, McCloskey, J.A., Ed., Academic Press, San Diego, 1990; 193: 647-60.
34. Oates JE, Dell A, Fukuda M, Fukuda MN. A rapid mass-spectrometric procedure for probing the non-reducing structures of lactosaminoglycan-containing glycoconjugates. Carbohydr Res 1985; 141: 149-52.
35. Karas M, Bahr U. Matrix-Assisted Laser Desorption- Ionisation (MALDI) Mass Spectrometry: Principles and Applications. Selected topics Mass spectrom Biomolecular Sciences, NATO ASI Series C, 1997, 504, 33.
36. Karas M, Hillenkamp F. Laser desorption ionisation of proteins with molecular masses exceeding 10, 000 daltons. Anal Chem 1988; 60: 2299-301.
37. Karas M, Bachmann D, Hillenkamp F. Influence of the wavelength in high-irradiance ultraviolet laser desorption mass spectrometry of organic molecules. Anal Chem 1985; 57: 2935-39.
38. Karas M, Bachmann D, Bahr U, Hillenkamp F. Matrix-assisted ultraviolet laser desorption of non-volatile compounds. Int J Mass Spectrom Ion Processes 1987; 78: 53-68.
39. Huberty M, C, Vath JE, Yu W, Martin SA. Site-specific carbohydrate identification in recombinant proteins using MALD-TOF MS. Anal. Chem. 1993; 65: 2791-800.
40. Shen X, Perreault H. Characterisation of carbohydrates using a combination of derivatisation, high-performance liquid chromatography and mass spectrometry. J Chromatogr A 1998; 811: 47-59.
41. Whittal RM, Li L. High-resolution matrix-assisted laser desorption/ionisation in a linear time-of-flight mass spectrometer. Anal Chem 1995; 67: 1950-4.
42. Shevehenko A, Loboda A, Shevehenko A, Ens W, Standing KG. MALDI quadrupole time-of-flight mass spectrometry: a powerful tool for proteomic research. Anal Chem 2000; 72: 2132-41.
43. Harvey DJ, Bateman RH, Bordoli RS, Tyldesley R. Ionisation and fragmentation of complex glycans with a quadrupole time-of-flight mass spectrometer fitted with a matrix-assisted laser desorption/ionisation ion source. Rapid Commun Mass Spectrom 2000; 14: 2135-42.
44. Tang L, Kebarle P. Effect of the conductivity of the electrosprayed solution on the electrospray current. Factors determining analyte sensitivity in electrospray mass spectrometry. Anal Chem 1991; 63: 2709-15.
45. Tang L, Kebarle P. Dependence of ion intensity in electrospray mass spectrometry on the concentration of the analytes in the electrosprayed solution. Anal Chem 1993; 65: 3654-68.
46. Kebarle P. A brief overview of the present status of the mechanisms involved in electrospray mass spectrometry. J Mass Spectrom 2000; 25: 804-17.
47. Hunt DF, Yates JR, Shabanowitz J, Winston S, Hauer CR. Protein sequencing by tandem mass spectrometry. Proc Natl Acad Sci USA 1986; 83: 6233-7.
48. Mo W, Sakamoto H, Nishikawa A, Kagi N, Langridge JI, Shimonishi Y, et al. Structural characterisation of chemically derivatised oligosaccharides by nanoflow electrospray ionisation mass spectrometry. Anal Chem 1999; 71: 4100-6.
49. Chait BT, Kent SBH. Weighing naked proteins: practical, high-accuracy mass measurement of peptides and proteins. Science 1992; 257: 1885-94.
50. Dai Y, Whittal RM, Li L, Weinberger SR. Accurate mass measurement of oligonucleotides using a time-lag focusing matrix-assisted laser desorption/ionisation time-of-flight mass spectrometer. Rapid Commun Mass Spectrom 1996; 10: 1792-6.
51. Fukai T, Kuroda J, Nomura T. Accurate mass measurement of low molecular weight compounds by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. J Am Soc Mass Spectrom 2000; 11: 458-63.
52. Wada Y, Gu JG, Okamoto N, Inui K. Diagnosis of carbohydrate-deficient giycoprotein syndrome by matrix-assisted laser desorption time-of-flight mass spectrometry. Biol Mass Spectrom 1994; 23: 108-9.
53. Chait BT, Wang R, Beavis RC, Kent SB. Protein ladder sequencing. Science 1993; 262: 89-92.
54. Nelson RW, Dogruel D, Williams P. Detection of human IgM at m/z approximately 1 MDa. Rapid Commun Mass Spectrom 1995; 9: 625.
55. Siegel MM, et al. Matrix-assisted UV-laser desorption/ionisation mass spectrometric analysis of monoclonal antibodies for the determination of carbohydrate, conjugated chelator, and conjugated drug content. Anal Chem 1991; 63: 2470-81.
56. Hedrich HC, Isobe K, Stahl B, Nokihara K, Kordel M, Schmid RD, et al. Matrix-assisted ultraviolet laser desorption/ionisation mass spectrometry applied to multiple forms of lipases. Anal Biochem 1993; 211: 288-92.
57. Tsarbopoulos A, Karas M, Strupat K, Pramanik BN, Nagabbushan TL, Hillenkamp F. Comparative mapping of recombinant proteins and glycoproteins by plasma desorption and matrix-assisted laser desorption/ionisation mass spectrometry. Anal Chem 1994; 66: 2062-70.
58. Rajan N, Tsarbopoulos A, Kumarasamy R, O'Donnell R, Taremi SS, Baldwin SW, et al. Characterisation of recombinant human interleukin 4 receptor from CHO cells: role of N-linked oligosaccharides. Biochem Biophys Res Commun 1995; 206: 694-702.
59. Harmon BJ, Gu X, Wang DIC. Rapid monitoring of site-specific glycosylation microheterogeneity of recombinant human interferon-gamma. Anal Chem 1996; 68: 1465-73.
60. Chakel A, Pungor E, Hancock WS, Swedberg SA. Analysis of recombinant DNA-derived glycoproteins via high-performance capillary electrophoresis coupled with off-line matrix-assisted laser desorption ionisation time-of-flight mass spectrometry. J Chromatogr B 1997; 689: 215-20.
61. Apffel A, Chakel A, Udiavar S, Hancock WS, Souders C, Pungor E. Application of capillary electrophoresis, high-performance liquid chromatography, on-line electrospray mass spectrometry and matrix-assisted laser desorption ionisation - time of flight mass spectrometry to the characterisation of single-chain plasminogen activator. J Chromatogr A 1995; 717: 41-60.
62. Ashton DS, et al. Characterisation of Recombinant Human Interleukin 4 Receptor from CHO Cells: Role of N-Linked Oligosaccharides. Biochem Biophys Res Commun 1995; 206: 694-702.
63. Smith MA. Mass Spectrometry of the Humanized Monoclonal Antibody Campata 1H. Anal Chem 1995; 67: 835-42.
64. Zaia J, Boynton R, Heinegård D, Barry F. Posttranslational modifications to human bone sialoprotein determined by mass spectrometry. Biochemistry 2001; 40: 12983-91.
65. Bonfichi R, Sottani C, Colombo L, Coutant JE, Riva E, Zanette D. Preliminary investigation of glycosylated proteins by capillary electrophoresis and capillary electrophoresis/mass spectrometry using electrospray ionisation and by matrix-assisted laser desorption ionisation/time-to-flight mass spectrometry. Rapid Commun Mass Spectrom 1995; S95-S106.
66. Sottani C, Fiorentino M, Minoia C. Matrix performance in matrix-assisted laser desorption/ionisation for molecular weight determination in sialyl and non-sialyl oligosaccharide proteins. Rapid Commun Mass Spectrom 1997; 11: 907-13.
67. Beavis RC, Chait BT. Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins. Rapid Commun Mass Spectrom 1989; 3: 432-5.
68. Pitt JJ, Gorman JJ. Oligosaccharide Characterisation and Quantitation Using 1-Phenyl-3-methyl-5-pyrazolone Derivatisation and Matrix-Assisted Laser Desorption/Ionisation Time-of-Flight Mass Spectrometry. Anal Biochem 1997; 248: 63-75.
69. Juhasz P, Costello CE, Biemann K. Matrix-assisted laser desorption ionisation mass spectrometry with 2-(4-hydroxyphenylazo)benzoic acid matrix. J Am Soc Mass Spectrom 1993; 4: 399-409.
70. Bahr U, Stahl-Zeng J, Gleitsmann E, Karas M. Delayed extraction time-of-flight MALDI mass spectrometry of proteins above 25,000 Da. J Mass Spectrom 1997; 32: 1111-6.
71. Vestal ML, Juhasz P, Martin SA. Delayed extraction matrix-assisted laser desorption time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 1995; 9: 1044-50.
72. Kim YJ, Freas A, Fenselau C. Analysis of viral glycoproteins by MALDI-TOF mass spectrometry. Anal Chem 2001; 73: 1544-8.
73. Denzinger T, Diekmann H, Bruns K, Laessing U, Stuermer C, Przybyski M. Isolation, primary structure characterisation and identification of the glycosylation pattern of recombinant goldfish neurolin, a neuronal cell adhesion protein. J Mass Spectrom 1999; 34: 435-46.
74. Belgacem O, Buchacher A, Pock K, Josic D, Sutton C, Rizzi A, et al. Molecular mass determination of plasma-derived glycoproteins by ultraviolet matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry with internal calibration. J Mass Spectrom 2002; 27: 1118-30.
75. Wada Y, Gu J, Okamoto N, Inui K. Diagnosis of carbohydrate-deficient glycoprotein syndrome by matrix-assisted laser desorption time-of-flight mass spectrometry. Biol Mass Spectrom 1994; 23: 108-9.
76. Feng R, Konishi Y. Analysis of antibodies and other large glycoproteins in the mass range of 150,000-200,000 Da by electrospray ionisation mass spectrometry. Anal Chem 1992; 64: 2090-5.
77. Wilm M, Mann M. Analytical properties of the nanoelectrospray ion source. Anal Chem 1996; 68: 1-8.
78. Duffin KL, Welply JK, Huang E, Henion JD. Characterisation of N-linked oligosaccharides by electrospray and tandem mass spectrometry. Anal Chem 1992; 64: 1440-8.
79. Karas M, Bahr U, Dülcks Fresenius J. Nano-electrospray ionisation mass spectrometry: addressing analytical problems beyond routine. Anal Chem 2000; 366: 669-76.
80. Hui JPM, White TC, Thibault P. Identification of glycan structure and glycosylation sites in cellobiohydrolase II and endoglucanases I and II from Trichoderma reesei. Glycobiology 2002; 12: 837-49.
81. Carr SA, Barr JR, Roberts GD, Anumula KR, Taylor PB. Identification of attachment sites and structural classes of asparagine-linked carbohydrates in glycoproteins. Methods Enzymol 1990; 193: 501-18.
82. Carr SA, Huddleston MJ, Bean MF. Selective identification and differentiation of N- and O-linked oligosaccharides in glycoproteins by liquid chromatography-mass spectrometry. Protein Sci 1993; 2: 183-96.
83. Huberty MC, Vath JE, Yu W, Martin SA. Site-specific carbohydrate identification in recombinant proteins using MALD-TOF MS. Anal Chem 1993; 65: 2791-800.
84. Huddleston MJ, Bean MF, Carr SA. Collisional fragmentation of glycopeptides by electrospray ionisation LC/MS and LC/MS/MS: methods for selective detection of glycopeptides in protein digests. Anal Chem 1993; 65: 877-84.
85. Hunter AP, Games DE. Evaluation of glycosylation site heterogeneity and selective identification of glycopeptides in proteolytic digests of bovine alpha 1-acid glycoprotein by mass spectrometry. Rapid Commun Mass Spectrom 1995; 9: 42-56.
86. Yang Y, Orlando R. Identifying the Glycosylation Sites and Site-specific Carbohydrate Heterogeneity of Glycoproteins by Matrix-assisted Laser Desorption/Ionisation Mass Spectrometry. Rapid Commun Mass Spectrom 1996; 10: 932-6.
87. 18O-labeling of N-glycosylation sites to improve the identification of gel-separated glycoproteins using peptide mass mapping and database searching. Anal Chem 1999; 71: 1431-40.
88. Mills K, Johnson AW, Diettrich O, Clayton PT, Winchester BG. A strategy for the identification of site-specific glycosylation in glycoproteins using MALDI TOF MS. Tetrahedron Asym 2000; 11: 75-93.
89. Mills K, Mills PB, Clayton PT, Johnson AW, Whitehouse DB, Winchester BG. Identification of alpha(1)-antitrypsin variants in plasma with the use of proteomic technology. Clin Chem 2001; 47: 2012-22.
90. 1-antitrypsin in congenital disorders of glycosylation type I is not random. Glycobiology 2003; 13: 73-85.
91. Wolf SM, Ferrari RP, Traversa S, Biemann K. Determination of the carbohydrate composition and the disulfide bond linkages of bovine lactoperoxidase by mass spectrometry. J Mass Spectrom 2000; 35: 210-7.
92. Sutton CW, Cottrell JS. In: Newer Methods in Glycoprotein and glycolipids characterisation, Cumming D, Reinhold VN, Ed., Academic Press, London, 1994.
93. Sutton CW, O'Neil JA, Cottrell JS. Site-specific characterisation of glycoprotein carbohydrates by exoglycosidase digestion and laser desorption mass spectrometry. Anal Biochem 1994; 218: 34-46.
94. Stahl B, Klabunde T, Witzel H, Krebs B, Steup M, Karas M, et al. The oligosaccharides of the Fe(III)-Zn(II) purple acid phosphatase of the red kidney bean. Determination of the structure by a combination of matrix-assisted laser desorption/ionisation mass spectrometry and selective enzymic degradation. Eur J Biochem 1994; 220: 321-330.
95. Yang Y, Bergmann C, Benen J, Orlando R. Identification of the glycosylation site and glycan structures of recombinant endopolygalacturonase II by mass spectrometry. Rapid Commun Mass Spectrom 1997; 11: 1257-62.
96. Zeng C, Biemann K. Determination of N-linked glycosylation of yeast external invertase by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. J Mass Spectrom 1999; 34: 311-29.
97. Mehlert A, Bond CS, Ferguson MAJ. The glycoforms of a Trypanosoma brucei variant surface glycoprotein and molecular modeling of a glycosylated surface coat. Glycobiology 2002; 12: 607-12.
98. Wang F, Nakouzi A, Angeletti RH, Casadevall A. Site-specific characterisation of the N-linked oligosaccharides of a murine immunoglobulin M by high-performance liquid chromatography/electrospray mass spectrometry. Anal Biochem 2003; 314: 266-80.
99. Zhen Y, Caprioli RM, Staros JV. Characterisation of glycosylation sites of the epidermal growth factor receptor. Biochemistry 2003; 42: 5478-92.
100. Ma S, Hill KE, Burk RF, Caprioli RM. Mass spectrometric identification of N- and O-glycosylation sites of full-length rat selenoprotein P and determination of selenide-sulfide and disulfide linkages in the shortest isoform. Biochemistry 2003; 42: 9703-11.
101. Rouse JC, Vath JE. On-the-probe sample cleanup strategies for glycoprotein-released carbohydrates prior to matrix-assisted laser desorption-ionisation time-of-flight mass spectrometry. Anal. Biochem 1996; 238: 82-92.
102. Küster B, Naven TJP, Harvey DJ. Rapid approach for sequencing neutral oligosaccharides by exoglycosidase digestion and matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. J Mass Spectrom 1996; 31: 1131-40.
103. Yang Y, Orlando R. Simplifying the Exoglycosidase Digestion/MALDI-MS Procedures for Sequencing N-Linked Carbohydrate Side Chains. Anal Chem 1996; 68: 570-2.
104. Colangelo J, Orlando R. On-target exoglycosidase digestions/MALDI-MS for determining the primary structures of carbohydrate chains. Anal Chem 1999; 71: 1479-82.
105. Mechref Y, Novotny MV. Mass spectrometric mapping and sequencing of N-linked oligosaccharides derived from submicrogram amounts of glycoproteins. Anal Chem 1998; 70: 455-63.
106. Colangelo J, Orlando R. On-target endoglycosidase digestion matrix-assisted laser desorption/ionisation mass spectrometry of glycopeptides. Rapid Commun Mass Spectrom 2001; 15: 2284-9.
107. Goletz S, Thiede B, Hanisch FG, Schultz M, Peter-Katalinic J, Müller S, et al. A sequencing strategy for the localization of O-glycosylation sites of MUC1 tandem repeats by PSD-MALDI mass spectrometry. Glycobiology 1997; 7: 881-96.
108. Müller S, Goletz S, Packer N, Gooley A, Lawson AM, Hanisch FG. Localization of O-glycosylation sites on glycopeptide fragments from lactation-associated MUC1. All putative sites within the tandem repeat are glycosylation targets in vivo. J Biol Chem 1997; 272: 24780-93.
109. Goletz S, Leuck M, Franke P, Karsten U. Structure analysis of acetylated and non-acetylated O-linked MUC1-glycopeptides by post-source decay matrix-assisted laser desorption/ionisation mass spectrometry. Rapid Commun Mass Spectrom 1997; 11: 1287-98.
110. Alving K, Körner R, Paulsen H, Peter-Katalinic J. Nanospray-ESI low-energy CID and MALDI post-source decay for determination of O-glycosylation sites in MUC4 peptides. J Mass Spectrom 1998; 33: 1124-33.
111. Greis KD, Hayes BK, Comer FI, Kirk M, Barnes S, Lowary TL, et al. Selective detection and site-analysis of O-GlcNAc-modified glycopeptides by beta-elimination and tandem electrospray mass spectrometry. Anal Biochem 1996; 234: 38-49.
112. Rademaker GJ, Pergantis SA, Bloktip L, Langridge JI, Kleen A, Thomas-Oates JE. Mass spectrometric determination of the sites of O-glycan attachment with low picomolar sensitivity. Anal Biochem 1998; 257: 149-60.
113. Hanisch FG, Jovanovic M, Peter-Katalinic J. Glycoprotein identification and localization of O-glycosylation sites by mass spectrometric analysis of deglycosylated/alkylaminylated peptide fragments. Anal Biochem 2001; 290: 47-59.
114. Mirgorodskaya E, Hassan H, Wandall HH, Clausen H, Roepstorff P. Partial vapor-phase hydrolysis of peptide bonds: A method for mass spectrometric determination of O-glycosylated sites in glycopeptides. Anal Biochem 1999; 269: 54-65.
115. Mirgorodskaya E, Hassan H, Clausen H, Roepstorff P. Mass spectrometric determination of O-glycosylation sites using beta-elimination and partial acid hydrolysis. Anal Chem 2001: 73: 1263-9.
116. Andersen JS, Svensson B, Roepstorff P. Electrospray ionisation and matrix assisted laser desorption/ionisation mass spectrometry: powerful analytical tools in recombinant protein chemistry. Nature Biotechnol 1996; 14: 449-57.
117. Flahaut C, Capon C, Balduyck M, Ricart G, Sautière P, Mizon J. Glycosylation pattern of human inter-alpha-inhibitor heavy chains. Biochem J 1998; 333: 749-56.
118. Iwase H, Tanaka A, Hiki Y, Kokubo T, Ishii-Karakasa I, Kobayashi Y, et al. Estimation of the number of O-linked oligosaccharides per heavy chain of human serum IgA1 by matrix-assisted laser desorption ionisation time-of-flight mass spectrometry (MALDI-TOFMS) analysis of the hinge glycopeptide. J Biochem 1996; 120: 393-7.
119. Udiavar S, Apffel A, Chakel J, Swedberg S, Hancock WS, Pungor E. The Use of Multidimensional Liquid-Phase Separations and Mass Spectrometry for the Detailed Characterisation of Posttranslational Modifications in Glycoproteins. Anal Che 1998; 70: 3572-8.
120. Geng M, Zhang X, Bina M, Regnier F. Proteomics of glycoproteins based on affinity selection of glycopeptides from tryptic digests. J Chromatogr B 2001; 752: 293-306.
121. Zhang H, Li XJ, Martin DB, Aebersold R. Identification and quantification of N-linked glycoproteins using hydrazide chemistry, stable isotope labeling and mass spectrometry. Nat Biotechnol 2003; 21: 660-6.
122. Zhu X, Borchers C, Bienstock RJ, Tomer KB. Mass spectrometric characterisation of the glycosylation pattern of HIV-gp120 expressed in CHO cells. Biochemistry 2000; 39: 11194-204.
123. Nemeth JF, Hochensang GP, Marnett LJ, Caprioli RM. Characterisation of the glycosylation sites in cyclooxygenase-2 using mass spectrometry. Biochemistry 2001; 40: 3109-16.
124. Schuette CG, Weisgerber J, Sandhoff K. Complete analysis of the glycosylation and disulfide bond pattern of human beta-hexosaminidase B by MALDI-MS. Glycobiology 2001; 11: 549-56.
125. Chong JM, Speicher DW. Determination of disulfide bond assignments and N-glycosylation sites of the human gastrointestinal carcinoma antigen GA733-2 (CO17-1A, EGP, KS1-4, KSA, and Ep-CAM). J Biol Chem 2001; 276: 5804-13.
126. Xiong L, Regnier FE. Use of a lectin affinity selector in the search for unusual glycosylation in proteomics. J Chromatogr B 2002; 782: 405-18.
127. Ling V, Guzzetta AW, Canova-Davis E, Stults JT, Hancock WS, Covey TR, et al. Characterisation of the tryptic map of recombinant DNA derived tissue plasminogen activator by high-performance liquid chromatography-electrospray ionisation mass spectrometry. Anal Chem 1991; 63: 2909-15.
128. Guzzetta AW, Basa LJ, Hancock WS, Keyt BA, Bennett WF. Identification of carbohydrate structures in glycoprotein peptide maps by the use of LC/MS with selected ion extraction with special reference to tissue plasminogen activator and a glycosylation variant produced by site directed mutagenesis. Anal Chem 1993; 65: 2953-62.
129. Vu-Hai M-T, Huet JC, Echasserieau K, Bidart JM, Floiras C, Pernollet JC, et al. Posttranslational modifications of the lutropin receptor: mass spectrometric analysis. Biochemistry 2000; 39; 5509-17.
130. Hirayama K, Yuji R, Yamada N, Kato K, Arata Y, Shimada I. Complete and rapid peptide and glycopeptide mapping of mouse monoclonal antibody by LC/MS/MS using ion trap mass spectrometry. Anal Chem 1998; 70: 2718-25.
131. Neumann GM, Marinaro JA, Bach LA. Identification of O-glycosylation sites and partial characterisation of carbohydrate structure and disulfide linkages of human insulin-like growth factor binding protein 6. Biochemistry 1998; 37: 6572-85.
132. Shimizu T, Miyairi K, Okuno T. Determination of glycosylation sites, disulfide bridges, and the C-terminus of Stereum purpureum mature endopolygalacturonase I by electrospray ionisation mass spectrometry. Eur J Biochem 2000; 267: 2330-9.
133. Medzihradszky KF, Maltby DA, Hall SC, Settineri CA, Burlingame AL. Characterisation of protein N-glycosylation by reversed-phase microbore liquid chromatography/electrospray mass spectrometry, complementary mobile phases, and sequential exoglycosidase digestion. J Am Soc Mass Spectrom 1994; 5: 350-8.
134. Rush RS, Derby PL, Smith DM, Merry C, Rogers G, Rohde MF, et al. Microheterogeneity of erythropoietin carbohydrate structure. Anal Chem 1995; 67: 1442-52.
135. Bloom JW, Madanat MS, Ray MK. Cell line and site specific comparative analysis of the N-linked oligosaccharides on human ICAM-1des454-532 by electrospray ionisation mass spectrometry. Biochemistry 1996; 35: 1856-64.
136. Colangelo J, Licon V, Benen J, Visser J, Bergmann C, Orlando R. Rapid Commun. Mass Spectrom 1999; 13: 1448.
137. Colangelo J, Licon V, Benen J, Visser J, Bergmann C, Orlando R. Characterisation of the N-linked glycosylation site of recombinant pectate lyase. Rapid Commun Mass Spectrom 1999; 13: 2382-7.
138. Kawasaki N, Ohta M, Hyuga S, Hayakawa T. Application of liquid chromatography/mass spectrometry and liquid chromatography with tandem mass spectrometry to the analysis of the site-specific carbohydrate heterogeneity in erythropoietin. Anal Biochem 2000; 285: 82-91.
139. Burlingame AL. Characterisation of protein glycosylation by mass spectrometry. Curr Opin Biotechnol 1996; 7: 4-10.
140. Strub JM, Sorokine O, Van Dorsselaer A, Aunis D, Metz-Boutigue MH. Phosphorylation and O-glycosylation sites of bovine chromogranin A from adrenal medullary chromatin granules and their relationship with biological activities. J Biol Chem 1997; 272: 11928-36.
141. Medzihradszky KF, Besman MJ, Burlingame AL. Structural characterisation of site-specific N-glycosylation of recombinant human factor VIII by reversed-phase high-performance liquid chromatography-electrospray ionisation mass spectrometry. Anal Chem 1997; 69: 3986-94.
142. Dage JL, Ackermann BL, Halsall HB. Site localization of sialyl Lewis(x) antigen on alpha1-acid glycoprotein by high performance liquid chromatography-electrospray mass spectrometry. Glycobiology 1998; 8: 755-60.
143. Stimson E, Hope J, Chong A, Burlingame AL. Site-specific characterisation of the N-linked glycans of murine prion protein by high-performance liquid chromatography/electrospray mass spectrometry and exoglycosidase digestions. Biochemistry 1999; 38: 4885-95.
144. Itoh S, Kawasaki N, Ohta M, Hayakawa T. Structural analysis of a glycoprotein by liquid chromatography-mass spectrometry and liquid chromatography with tandem mass spectrometry. Applications to recombinant human thrombomodulin. J Chromatogr A 2002; 978: 141-52.
145. Ritchie MA, Gil AC, Deery MJ, Lilley K. Precursor ion scanning for detection and structural characterisation of heterogeneous glycopeptide mixtures. J Am Soc Mass Spectrom 2002; 13: 1065-77.
146. Rudd PM, et al. Glycosylation differences between the normal and pathogenic prior protein isoforms. Proc Natl Acad Sci USA 1999; 96: 13044-9.
147. Haltiwanger RS, Busby S, Grove K, Li S, Mason D, Medina L, et al. O-glycosylation of nuclear and cytoplasmic proteins: regulation analogous to phosphorylation? Biochem Biophys Res Commun 1997; 231: 237-42.
148. Hart GW. Dynamic O-linked glycosylation of nuclear and cytoskeletal proteins. Annu Rev Biochem 1997; 66: 315-35.
149. Carr SA, Huddleston MJ, Annan RS. Selective detection and sequencing of phosphopeptides at the femtomole level by mass spectrometry. Anal Biochem 1996; 239: 180-92.
150. Haynes PA, Aebersold R. Simultaneous detection and identification of O-GlcNAc-modified glycoproteins using liquid chromatography-tandem mass spectrometry. Anal Chem 2000; 72: 5402-10.
151. Morris HR, Paxton T, Panico M, McDowell R, Dell A. A novel geometry mass spectrometer, the Q-TOF, for low-femtomole/attomole-range biopolymer sequencing. J Protein Chem 1997; 16: 469-79.
152. Chalkley RJ, Burlingame AL. Identification of GlcNAcylation sites of peptides and α-crystallin using Q-TOF mass spectrometry. J Am Soc Mass Spectrom 2001; 12: 1106-13.
153. Wells L, Vosseler K, Cole RN, Cronshaw JM, Matunis MJ, Hart GW. Mapping sites of O-GlcNAc modification using affinity tags for serine and threonine post-translational modifications. Mol Cell Proteomics 2002; 1: 791-804.
154. Czeszak X, Ricart G, Tetaert D, Michalski JC, Lemoine J. Identification of substituted sites on MUC5AC mucin motif peptides after enzymatic O-glycosylation combining beta-elimination and fixed-charge derivatisation. Rapid Commun Mass Spectrom 2002; 16: 27-34.
155. Hanisch FG, Green BN, Bateman R, Peter-Katalinic J. Localization of O-glycosylation sites of MUC1 tandem repeats by QTOF ESI mass spectrometry. J Mass Spectrom 1998; 33: 358-62.
156. Alving K, Paulsen H, Peter-Katalinic J. Characterisation of O-glycosylation sites in MUC2 glycopeptides by nanoelectrospray QTOF mass spectrometry. J Mass Spectrom 1999; 34: 395-407.
157. Macek B, Hofsteenge J, Peter-Katalinic J. Direct determination of glycosylation sites in O-fucosylated glycopeptides using nano-electrospray quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 2001; 15: 771-7.
158. Müller S, Alving K, Peter-Katalinic J, Zachara N, Gooley AA, Hanisch FG. High density O-glycosylation on tandem repeat peptide from secretory MUC1 of T47D breast cancer cells. J Biol Chem 1999; 274: 18165-72.
159. Schmitt S, Glebe D, Alving K, Tolle TK, Linder M, Geyer H, et al. Analysis of the pre-S2 N- and O-linked glycans of the M surface protein from human hepatitis B virus. J Biol Chem 1999; 274: 11945-57.
160. Boja ES, Hoodbhoy T, Fales HM, Dean J. Structural characterisation of native mouse zona pellucida proteins using mass spectrometry. J Biol Chem 2003; 278: 34189-202.
161. Emmett MR. Determination of post-translational modifications of proteins by high-sensitivity, high-resolution Fourier transform ion cyclotron resonance mass spectrometry. J Chromatogr A 2003; 1013: 203-13.
162. Loo JA, Quinn JP, Ryu SI, Henry KD, Senko MW, McLafferty MW. High-resolution tandem mass spectrometry of large biomolecules. Proc Natl
163. Jensen PK, Pasa-Tolic I, Anderson GA, Horner JA, Lipton MS, Bruce JE, et al. Probing proteomes using capillary isoelectric focusing-electrospray ionisation Fourier transform ion cyclotron resonance mass spectrometry. Anal Chem 1999; 71: 2076-84.
164. Senko MW, Speir JP, McLAfferty FW. Collisional activation of large multiply charged ions using Fourier transform mass spectrometry. Anal Chem 1994; 66: 2801-8.
165. Jockusch RA, Schnier PD, Price WD, Strittmatter EF, Demirev PA, Williams ER. Effects of charge state on fragmentation pathways, dynamics, and activation energies of ubiquitin ions measured by blackbody infrared radiative dissociation. Anal Chem 1997; 69: 1119-26.
166. Kruger NA, Zubarev RA, Carpenter BK, Kelleher NL, Horn DM, McLafferty FW. Electron capture versus energetic dissociation of protein ions. Int J Mass Spectrom 1999; 183: 1-5.
167. Zubarev RA, Kelleher NL, McLafferty FW. Electron Capture Dissociation of Multiply Charged Protein Cations. A Nonergodic Process. J Am Chem Soc 1998; 120: 3265-6.
168. McLuckey SA, van Berkel GJ, Glish GL. Tandem mass spectrometry of small, multiply charged oligonucleotides. J Am Soc Mass Spectrom 1992; 3: 60-70.
169. Little DP, Speir JP, Senko MW, O'Connor PB, McLafferty FW. Infrared multiphoton dissociation of large multiply charged ions for biomolecule sequencing. Anal Chem 1994; 66: 2809-15.
170. Zubarev RA, Horn DM, Fridriksson EK, Kelleher NL, Kruger NA, Lewis MA, et al. Electron Capture Dissociation for Structural Characterisation of Multiply Charged Protein Cations. Anal Chem 2000; 72: 563-73.
171. McLafferty FW, Horn DM, Breuker K, Ge Y, Lewis MA, Cerda B, et al. Electron capture dissociation of gaseous multiply charged ions by fourier-transform ion cyclotron resonance. J Am Soc Mass Spectrom 2001; 12: 245-9.
172. Roepstorff P, Fohlman J. Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed Mass Spectrom 1984; 11: 601.
173. Zubarev RA, Kruger NA, Fridriksson EK, Lewis MA, Horn DM, Carpenter BK, et al. Electron Capture Dissociation of Gaseous Multiply-Charged Proteins Is Favored at Disulfide Bonds and Other Sites of High Hydrogen Atom Affinity. J Am Chem Soc 1999; 121: 2857-62.
174. Mirgorodskaya E, Roepstorff P, Zubarev RA. Localization of O-glycosylation sites in peptides by electron capture dissociation in a Fourier transform mass spectrometer. Anal Chem 1999; 71: 4431-6.
175. Haselmann KF, Budnik BA, Olsen JV, Nielsen ML, Reis CA, Clausen H, et al. Advantages of external accumulation for electron capture dissociation in Fourier transform mass spectrometry. Anal Chem 2001; 73: 2998-3005.
176. Håkansson K, Cooper HJ, Emmett MR, Costello CE, Marshall AG. Nilsson CL. Electron capture dissociation and infrared multiphoton dissociation MS/MS of an N-glycosylated tryptic peptic to yield complementary sequence information. Anal Chem 2001; 73: 4530-6.
177. Fridriksson EK, Beavil A, Holowka D, Gould HJ, Baird B, McLafferty FW. Heterogeneous glycosylation of immunoglobulin E constructs characterized by top-down high-resolution 2-D mass spectrometry. Biochemistry 2000; 39: 3369-76.
178. Kjeldsen F, Haselmann KF, Budnik BA, Sørensen ES, Zubarev RA. Complete characterisation of posttranslational modification sites in the bovine milk protein PP3 by tandem mass spectrometry with electron capture dissociation as the last stage. Anal Chem 2003; 75: 2355-61.
179. Jorgenson JW, Lukacs KD. Zone electrophoresis in open-tubular glass capillaries. Anal Chem 1981; 53: 1298-302.
180. Lauer HH, McManigill D. Capillary zone electrophoresis of proteins in untreated fused silica tubing. Anal Chem 1986; 58: 166-70.
181. Green JS, Jorgenson JW. Variable-wavelength on-column fluorescence detector for open-tubular zone electrophoresis. J Chromatogr A 1986; 352: 337-43.
182. Smith RD, Barinaga CJ, Udseth HR. Improved electrospray ionisation interface for capillary zone electrophoresis-mass spectrometry. Anal Chem 1988; 60: 1948-52.
183. Wahl JH, Gale DC, Smith RD. Sheathless capillary electrophoresis-electrospray ionisation mass spectrometry using 10 mu m I.D. capillaries: analyses of tryptic digests of cytochrome c. J Chromatogr A 1994; 659: 217-22.
184. Kelly JF, Ramaley L, Thibault P. Capillary Zone Electrophoresis Electrospray Mass Spectrometry at Submicroliter Flow Rates: Practical Considerations and Analytical Performance. Anal Chem 1997; 69: 51-60.
185. Bateman KP, White RL, Yaguchi M, Thibault P. Characterisation of protein glycoforms by capillary-zone electrophoresis-nanoelectrospray mass spectrometry. J Chromatogr A 1998; 794: 327-44.
186. Bateman KP, White RL, Thibault P. Disposable Emitters for On-line Capillary Zone Electrophoresis/Nanoelectrospray Mass Spectrometry. Rapid Commun Mass Spectrom 1997; 11: 307-15.
187. Lai CC, Her GR. Analysis of phospholipase A2 glycosylation patterns from venom of individual bees by capillary electrophoresis/electrospray ionisation mass spectrometry using an ion trap mass spectrometer. Rapid Commun Mass Spectrom 2000; 14: 2012-8.
188. Liu T, Li JD, Zeng R, Shao XX, Wang KY, Xia QC. Capillary Electrophoresis-Electrospray Mass Spectrometry for the Characterisation of High-Mannose-Type N-Glycosylation and Differential Oxidation in Glycoproteins by Charge Reversal and Protease/Glycosidase Digestion. Anal Chem 2001; 73: 5875-85.
189. Boss HJ, Watson DB, Rush RS. Peptide capillary zone electrophoresis mass spectrometry of recombinant human erythropoietin: an evaluation of the analytical method. Electrophoresis 1998; 19: 2654-64.
190. Takasaki S, Misuochi T, Kobata A. Hydrazinolysis of asparagine-linked sugar chains to produce free oligosaccharides. Methods Enzymol 1982; 83: 263-8.
191. Patel T, Bruce J, Merry A, Bigge C, Wormald M, Jaques A, et al. Use of hydrazine to release in intact and unreduced form both N- and O-linked oligosaccharides from glycoproteins. Biochemistry 1993; 32: 679-93.
192. Costa J, Ashford DA, Nimtz M, Bento I, Frazao C, Esteves CL, et al. The glycosylation of the aspartic proteinases from barley (Hordeum vulgare L.) and cardoon (Cynara cardunculus L.). Eur J Biochem 1997; 243: 695-700.
193. Haslam SM, Coles GC, Munn EA, Smith TS, Smith HF, Morris HR, et al. Haemonchus contortus glycoproteins contain N-linked oligosaccharides with novel highly fucosylated core structures. J Biol Chem 1996; 271: 30561.
194. Takahashi N, Nishibe H. Some characteristics of a new glycopeptidase acting on aspartylglycosylamine linkages. J Biochem 1978; 84: 1467-73.
195. Tretter V, Altmann F, März L. Peptide-N4-(N-acetyl-beta-glucosaminyl)asparagine amidase F cannot release glycans with fucose attached alpha 1 ---- 3 to the asparagine-linked N-acetylglucosamine residue. Eur J Biochem. 1991; 199: 647-52.
196. Tarentino AL, Maley F. A comparison of the substrate specificities of endo-beta-N-acetylglucosaminidases from Streptomyces griseus and Diplococcus Pneumoniae. Biochem Biophys Res Commun 1975; 67: 455-62.
197. Tai T, Yamashita K, Ito S, Kobata A. Structures of the carbohydrate moiety of ovalbumin glycopeptide III and the difference in specificity of endo-beta-N-acetylglucosaminidases CII and H. J Biol Chem 1977; 252: 6687-94.
198. Trimble RB, Tarentino AL. Identification of distinct endoglycosidase (endo) activities in Flavobacterium meningosepticum: endo F1, endo F2, and endo F3. Endo F1 and endo H hydrolyze only high mannose and hybrid glycans. J Biol Chem 1991; 266: 1646-51.
199. Arakawa M, Muramatsu T. Endo-beta-N-acetylglucosaminidases acting on the carbohydrate moieties of glycoproteins. The differential specificities of the enzymes from Streptomyces griseus and Diplococcus pneumoniae. J Biochem 1974; 76: 307-17.
200. Maley F, Trimble RB, Tarentino AL, Plummer TH. Characterisation of glycoproteins and their associated oligosaccharides through the use of endoglycosidases. Anal Biochem 1989; 180: 195-204.
201. Tarentino AL, Plumer TH. Enzymatic deglycosylation of asparagine-linked glycans: purification, properties, and specificity of oligosaccharide-cleaving enzymes from Flavobacterium meningosepticum. Meth Enzymol 1994; 230: 44-57.
202. O'Neill RA. Enzymatic release of oligosaccharides from glycoproteins for chromatographic and electrophoretic analysis. J Chromatogr A 1996; 720: 201-15.
203. Carlson DM. Structures and immunochemical properties of oligosaccharides isolated from pig submaxillary mucins. J Biol Chem 1968; 243: 616-26.
204. Takasaki S, Yamashita K, Kobata A. The sugar chain structures of ABO blood group active glycoproteins obtained from human erythrocyte membrane. J Biol Chem 1978; 253: 6086-91.
205. Amano J, Nishimura R, Mochizuki M, Kobata A. Comparative study of the mucin-type sugar chains of human chorionic gonadotropin present in the urine of patients with trophoblastic diseases and healthy pregnant women. J Biol Chem 1988; 263: 1157-65.
206. Whittal RM, Palcic MM, Hindsgaul O, Li L. Direct analysis of enzymatic reactions of oligosaccharides in human serum using matrix-assisted laser desorption ionisation mass spectrometry. Anal Chem 1995; 67: 3509-14.
207. Yoshino KI, Takao T, Murata H, Shimonishi Y. Use of the derivatizing agent 4-aminobenzoic acid 2-(diethylamino)ethyl ester for high-sensitivity detection of oligosaccharides by electrospray ionisation mass spectrometry. Anal Chem 1995; 67: 4028-31.
208. Cooper CA, Packer NH, Redmond JW. The elimination of O-linked glycans from glycoproteins under non-reducing conditions. Glycoconjugate J 1994; 11: 163-7.
209. Chai W, Feizi T, Yuen CT, Lawson AM. Nonreductive release of O-linked oligosaccharides from mucin glycoproteins for structure/function assignments as neoglycolipids: application in the detection of novel ligands for E-selectin. Glycobiology 1997; 7: 861-72.
210. Hanisch FG, Jovanovic M, Peter-Katalinic J. Glycoprotein identification and localization of O-glycosylation sites by mass spectrometric analysis of deglycosylated/alkylaminylated peptide fragments. Anal Biochem 2001; 290: 47-59
211. Yuen CT, Lawson AM, Chai W, Larkin M. Stoll MS, Stuart AC, et al. Novel sulfated ligands for the cell adhesion molecule E-selectin revealed by the neoglycolipid technology among O-linked oligosaccharides on an ovarian cystadenoma glycoprotein. Biochemistry 1992; 31: 9126-31.
212. Huang Y, Mechref Y, Novotny MV. Microscale nonreductive release of O-linked glycans for subsequent analysis through MALDI mass spectrometry and capillary electrophoresis. Anal Chem 2001; 73: 6063-9.
213. Huang Y, Konse T, Mechref Y, Novotny MV. Matrix-assisted laser desorption/ionisation mass spectrometry compatible beta-elimination of O-linked oligosaccharides. Rapid Commun Mass Spectrom 2002; 16: 1199-204.
214. Huang CC, Aminoff D. Enzymes that destroy blood group specificity. V. The oligosaccharase of Clostridium perfringens. J Biol Chem 1972; 247: 6737-42.
215. Iwase H, Ishihara K, Tanaka Y, Omura S, Hotta K. Release of oligosaccharides possessing reducing-end N-acetylgalactosamine from mucus glycoprotein in Streptomyces sp. OH-11242 culture medium through action of endo-type glycosidase. Biochem Biophys Res Commun 1988; 151: 422-8.
216. Ishii-Karakasa I, Hotta K, Tanaka Y, Omura S. Partial purification and characterisation of an endo-alpha-N-acetylgalactosaminidase from the culture medium of Streptomyces sp. OH-11242. Biochem J 1992; 288: 475-82.
217. Dell A, Reason AJ, Khoo KH, Panico M, McDowell RA, Morris HR. Mass spectrometry of carbohydrate-containing biopolymers. Methods Enzymol 1994; 230: 108-32.
218. Sutton-Smith M, Morris HR, Dell A. A rapid mass spectrometric strategy suitable for the investigation of glycan alterations in knockout mice. Tetrahedron Assymetry 2000; 11: 363-9.
219. Sutton-Smith M, Morris HR, Grewal PK, Hewitt JE, Bittner RE, Goldin E, et al. In Glycogenomics: The Impact of Genomics and Informatics in Glycobiology Biochem Soc Symp 2002; 69: 105-15.
220. Chui D, Sellakumar G, Green RS, Marek KW, Sutton-Smith M, McQuistan T, et al. Genetic remodeling of protein glycosylation in vivo induces autoimmune disease. Proc Natl Acad Sci USA 2001; 98: 1142-7.
221. Wang Y, Tan J, Sutton-Smith M, Ditto D, Panico M, Campebell RM, et al. Modeling human congenital disorder of glycosylation type IIa in the mouse: conservation of asparagine-linked glycan-dependent functions in mammalian physiology and insights into disease pathogenesis. Glycobiology 2001; 11: 1051-70.
222. Haslam, SM, Gems D, Morris HR, Dell A. In Glycogenomics: The Impact of Genomics and Informatics in Glycobiology Biochem Soc Symp 2002, 69, 117-34.
223. Guérardel Y, Balanzino L, Maes E, Leroy Y, Coddeville B, Oriol R, et al. The nematode Caenorhabditis elegans synthesizes unusual O-linked glycans: identification of glucose-substituted mucin-type O-glycans and short chondroitin-like oligosaccharides. Biochem J 2001; 357: 167-82.
224. Altmann F, Fabini G, Ahorn H, Wilson IBH. Genetic model organisms in the study of N-glycans. Biochimie 2001; 83; 703-12.
225. Oriol R, Mollicone R, Cailleau LB, Breton C. Divergent evolution of fucosyltransferase genes from vertebrates, invertebrates, and bacteria. Glycobiology 1999; 9: 323-34.
226. Easton RL, Patankar MS, Clark GF, Morris HR, Dell A. Pregnancy-associated changes in the glycosylation of tammhorsfall glycoprotein. Expression of sialyl Lewis(x) sequences on core 2 type O-glycans derived from uromodulin. J Biol Chem 2000; 275: 21928-38.
227. Morelle W, Haslam SM, Ziak M, Roth J, Morris H, Dell A. Characterisation of the N-linked oligosaccharides of megalin (gp330) from rat kidney. Glycobiology 2000; 10: 295-304.
228. Suzuki N, Khoo KH, Chen HC, Johnson JR, Lee YC. Isolation and characterisation of major glycoproteins of pigeon egg white: ubiquitous presence of unique N-glycans containing Galalpha1-4Gal. J Biol Chem 2001; 276: 23221-9.
229. Haslam SM, Coles GC, Morris HR, Dell A. Structural characterisation of the N-glycans of Dictyocaulus viviparus: discovery of the Lewis(x) structure in a nematode. Glycobiology 2000; 10: 223-9.
230. Morelle W, Haslam SM, Morris HR, Dell A. Characterisation of the N-linked glycans of adult Trichinella spiralis. Mol Biochem Parasitol 2000; 109: 171-7.
231. Morelle W, Haslam SM, Olivier V, Appleton JA, Morris HR, Dell A. Phosphorylcholine-containing N-glycans of Trichinella spiralis: identification of multiantennary lacdiNAc structures. Glycobiology 2000; 10: 941-5.
232. Haslam SM, Houston KM, Harnett W, Reason AJ, Morris HR, Dell A. Structural studies of N-glycans of filarial parasites. Conservation of phosphorylcholine-substituted glycans among species and discovery of novel chito-oligomers. J Biol Chem 1999; 274: 20953-60.
233. Papac DI, Wong A, Jones AJS. Analysis of acidic oligosaccharides and glycopeptides by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Anal Chem 1996; 68: 3215-23.
234. Harvey DJ. Quantitative aspects of the matrix-assisted laser desorption mass spectrometry of complex oligosaccharides. Rapid Commun Mass Spectrom 1993; 7: 614-9.
235. Stahl B, Steup M, Karas M, Hillenkamp F. Analysis of neutral oligosaccharides by matrix-assisted laser desorption ionisation mass spectrometry. Anal Chem 1991; 63: 1463-6.
236. Gorisch H. Drop dialysis: time course of salt and protein exchange. Anal Biochem 1988; 173: 393-8.
237. Marusyk R, Sergeant A. A simple method for dialysis of small-volume samples. Anal Biochem 1980; 105: 403-4.
238. Bornsen KO, Mohr MD, Widmer HM. Matrix-assisted laser desorption/ionisation mass spectrometry: improved matrix for oligosaccharides. Rapid Commun Mass Spectrom 1995; 9: 809-14.
239. Kussmann M, Nordhoff E, Rehbek-Nielsen H, Haebel S, Rossel-Larsen M, Jakobsen L, et al. Matrix-assisted Laser Desorption/Ionisation Mass Spectrometry Sample Preparation Techniques Designed for Various Peptide and Protein Analytes. J Mass Spectrom 1997; 32: 593.
240. Packer NH, Lawson MA, Jardine DR, Redmond JW. A general approach to desalting oligosaccharides released from glycoproteins. Glycoconjugate J 1998; 15: 737-47.
241. Chen P, Baker AG, Novotny MV. The use of osazones as matrices for the matrix-assisted laser desorption/ionisation mass spectrometry of carbohydrates. Anal Biochem 1997; 244: 144-51.
242. Mechref Y, Zidek L, Ma W, Novotny MV. Glycosylated major urinary protein of the house mouse: characterisation of its N-linked oligosaccharides. Glycobiology 2000; 10: 231-5.
243. Papac DI, Briggs JB, Chin ET, Jones AJS. A high-throughput microscale method to release N-linked oligosaccharides from glycoproteins for matrix-assisted laser desorption/ionisation time-of-flight mass spectrometric analysis. Glycobiology 1998; 8: 445-54.
244. Henzel WJ, Grimley C, Bourell JH, Billeci TM, Wong SC, Stults JT. Analysis of Two-Dimensional Gel Proteins by Mass Spectrometry and Microsequencing. Methods 1994; 6: 239-47.
245. Küster B, Wheeler SF, Hunter AP, Dwek RA, Harvey DJ. Sequencing of N-linked oligosaccharides directly from protein gels: in-gel deglycosylation followed by matrix-assisted laser desorption/ionisation mass spectrometry and normal-phase high-performance liquid chromatography. Anal Biochem 1997; 250: 82-101.
246. Wheeler SF, Harvey DJ. Extension of the in-gel release method for structural analysis of neutral and sialylated N-linked glycans to the analysis of sulfated glycans: application to the glycans from bovine thyroid-stimulating hormone. Anal Biochem 2001; 296: 92-100.
247. Hoja-Lukowicz D, Ciolczyk D, Bergquist J, Litynska A, Laidler P. High-mannose-type oligosaccharides from human placental arylsulfatase A are core fucosylated as confirmed by MALDI MS. Glycobiology 2000; 10: 551-7.
248. Cancilla MT, Penn SG, Lebrilla CB. Alkaline degradation of oligosaccharides coupled with matrix-assisted laser desorption/ionisation Fourier transform mass spectrometry: a method for sequencing oligosaccharides. Anal Chem 1998; 70: 663-72.
249. Domon B, Costello CE. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J 1988; 5: 397-409.
250. Ngoka LC, Gal JF, Lebrilla CB. Effects of cations and charge types on the metastable decay rates of oligosaccharides. Anal Chem 1994; 66: 692-8.
251. Cancilla, MT, Penn SG, Carroll JA, Lebrilla CB. Coordination of Alkali Metals to Oligosaccharides Dictates Fragmentation Behavior in Matrix Assisted Laser Desorption Ionisation/Fourier Transform Mass Spectrometry. J Am Chem Soc 1996; 118: 6736-45.
252. Naven TJP, Harvey DJ, Brown J, Critchley G. Fragmentation of complex carbohydrates following ionisation by matrix-assisted laser desorption with an instrument fitted with time-lag focusing. Rapid Commun Mass Spectrom 1997; 11: 1681-6.
253. Harvey DJ, Naven TJP, Küster B, Bateman MR, Green G, Critchley G. Comparison of fragmentation modes for the structural determination of complex oligosaccharides ionised by matrix-assisted laser desorption/ionisation mass spectrometry. Rapid Commun Mass Spectrom 1995; 9: 1556-61.
254. Guanghong L, Marginean I, Vertes A. Internal Energy of Ions Generated by Matrix-Assisted Laser Desorption/Ionisation. Anal Chem 2002, 74: 6185-90.
255. Yamagaki T, Nakanishi H. Influence of acceleration voltages on relative ion intensities in the post-source decay fragmentation of isomeric cyclic oligosaccharides by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 1999; 13: 2199-203.
256. Spengler B, Kirsch D, Kaufmann R, Lemoine J. J Mass Spectrom 1995; 30: 782.
257. Garozzo D, Nasello V, Spina E, Sturiale L. Discrimination of isomeric oligosaccharides and sequencing of unknowns by post source decay matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 1997; 11: 1561-6.
258. Lemoine J, Chirat F, Domon B. Structural analysis of derivatised oligosaccharides using pest-source decay matrix-assisted laser desorption/ionisation mass spectrometry. J Mass Spectrom 1996; 31, 908-12.
259. Okamoto M, Takahashi KI, Doi T, Takimoto Y. High-Sensitivity Detection and Postsource Decay of 2-Aminopyridine-Derivatised Oligosaccharides with Matrix-Assisted Laser Desorption/Ionisation Mass Spectrometry. Anal Chem 1997; 69: 2919-26.
260. Sato Y, Suzuki M, Nirasawa T, Suzuki A, Endo T. Microsequencing of Glycans Using 2-Aminobenzamide and MALDI-TOF Mass Spectrometry: Occurrence of Unique Linkage-Dependent Fragmentation. Anal Chem 2000; 72: 1207-16.
261. Rouse JC, Strang AM, Yu W, Vath JE. Isomeric differentiation of asparagine-linked oligosaccharides by matrix-assisted laser desorption-ionisation postsource decay time-of-flight mass spectrometry. Anal Biochem 1998; 256: 33-46.
262. Yamagaki T, Nakanishi H. Post-source decay fragmentation analyses of linkage isomers of Lewis-type oligosaccharides in curved-field reflectron matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry: combined in-source decay/post-source decay experiments and relative ion abundance analysis. J Mass Spectrom 2000; 35: 1300-7.
263. Yamagaki T, Nakanishi H. Ion intensity analysis of post-source decay fragmentation in curved-field reflectron matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry of carbohydrates: for structural characterisation of glycosylation in proteome analysis. Proteomics 2001; 1: 329-39.
264. Cornish TJ, Cotter RJ. A curved-field reflectron for improved energy focusing of product ions in time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 1993; 7: 1037-40.
265. Cornish TJ, Cotter RJ. A curved field reflectron time-of-flight mass spectrometer for the simultaneous focusing of metastable product ions. Rapid Commun Mass Spectrom 1994; 8: 781-5.
266. Harvey DJ, Bateman RH, Green MR. High-energy collision-induced fragmentation of complex oligosaccharides ionised by matrix-assisted laser desorption/ionisation mass spectrometry. J Mass Spectrom 1997; 32: 167-87.
267. Spina E, Cozzolino R, Ryan E, Garozzo D. Sequencing of oligosaccharides by collision-induced dissociation matrix-assisted laser desorption/ionisation mass spectrometry. J Mass Spectrom 2000; 35: 1042-8.
268. Küster B, Naven TJP, Harvey DJ. Effect of the reducing-terminal substituents on the high energy collision-induced dissociation matrix-assisted laser desorption/ionisation mass spectra of oligosaccharides. Rapid Commun Mass Spectrom 1996; 10: 1645-51.
269. Penn SG, Cancilla MTk, Lebrilla CB. Collision-induced dissociation of branched oligosaccharide ions with analysis and calculation of relative dissociation thresholds. Anal Chem 1996; 68: 2331-9.
270. Tseng K, Lindsay LL, Penn S, Hedrick JL, Lebrilla CB. Characterisation of neutral oligosaccharide-alditols from Xenopus laevis egg jelly coats by matrix-assisted laser desorption Fourier transform mass spectrometry. Anal Biochem 1997; 250: 18-28.
271. Solouki T, Reinhold BB, Costello CE, O'Malley M, Guan S, Marshall AG. Electrospray ionisation and matrix-assisted laser desorption/ionisation Fourier transform ion cyclotron resonance mass spectrometry of permethylated oligosaccharides. Anal Chem 1998; 70: 857-64.
272. Charlwood J, Birrell H, Gribble A, Burdes V, Tolson D, Camilleri P. A probe for the versatile analysis and characterisation of N-linked oligosaccharides. Anal Chem 2000; 72: 1453-61.
273. Hanrahan S, Charlwood J, Tyldesley R, Langridge J, Bordoli R, Bateman R, et al. Facile sequencing of oligosaccharides by matrix-assisted laser desorption/ionisation on a hybrid quadrupole orthogonal acceleration time-of-flight mass spectrometer. Rapid Commun Mass Spectrom 2001; 11: 1141-51.
274. Laiko VV, Baldwin MA, Burlingame AL. Atmospheric pressure matrix-assisted laser desorption/ionisation mass spectrometry. Anal Chem 2000; 72: 652-7.
275. Creaser CS, Reynolds JC, Harvey DJ. Structural analysis of oligosaccharides by atmospheric pressure matrix-assisted laser desorption/ionisation quadrupole ion trap mass spectrometry. Rapid Commun Mass Spectrom 2002; 16: 176-84.
276. Moyer SC, Marzilli LA, Woods AS, Laiko VV, Doroshenko VM, Cotter RJ. Atmospheric pressure matrix-assisted laser desorption/ionisation (AP MALDI) on a quadrupole ion trap mass spectrometer. Int J Mass Spectrom 2003; 226: 133-50.
277. Von Seggern CE, Moyer SC, Cotter RJ. Liquid infrared atmospheric pressure matrix-assisted laser desorption/ionisation ion trap mass spectrometry of sialylated carbohydrates. Anal Chem 2003; 75: 3212-8.
278. Von Seggern CE, Zarek PE, Cotter RJ. Fragmentation of sialylated carbohydrates using infrared atmospheric pressure MALDI ion trap mass spectrometry from cation-doped liquid matrixes. Anal Chem 2003; 75: 6523-30.
279. Xie Y, Lebrilla CB. Infrared multiphoton dissociation of alkali metal-coordinated oligosaccharides. Anal Chem 2003; 75: 1590-8.
280. Cancilla MT, Wang AW, Voss LR, Lebrila CB. Fragmentation Reactions in the Mass Spectrometry Analysis of Neutral Oligosaccharides. Anal Chem 1999; 71: 3206-18.
281. Linsley KB, Chan SY, Chan S, Reinhold BB, Lisi PJ, Reinhold VN. Applications of electrospray mass spectrometry to erythropoietin N- and O-linked glycans. Anal Biochem 1994; 219: 207-17.
282. Okamoto M, Takahashi K, Doi T. Sensitive detection and structural characterisation of trimethyl(p-aminophenyl)-ammonium-derivatised oligosaccharides by electrospray ionisation-mass spectrometry and tandem mass spectrometry. Rapid Commun Mass Spectrom 1995; 9: 641-3.
283. Naven TJP, Harvey DJ. Effect of structure on the signal strength of oligosaccharides in matrix-assisted laser desorption/ionisation mass spectrometry on time-of-flight and magnetic sector instruments. Rapid Commun Mass Spectrom 1996; 10: 1361-6.
284. Li M, Kinzer JA. Structural analysis of oligosaccharides by a combination of electrospray mass spectrometry and bromine isotope tagging of reducing-end sugars with 2-amino-5-bromopyridine. Rapid Commun Mass Spectrom 2003; 17: 1462-6.
285. Viseux N, de Hoffmann E, Domon B. Structural analysis of permethylated oligosaccharides by electrospray tandem mass spectrometry. Anal Chem 1997; 69: 3193-8.
286. Sheeley DM, Reinhold VN. Structural characterisation of carbohydrate sequence, linkage, and branching in a quadrupole Ion trap mass spectrometer: neutral oligosaccharides and N-linked glycans. Anal Chem 1998; 70: 3053-9.
287. Viseux N, de Hoffmann E, Domon B. Structural assignment of permethylated oligosaccharide subunits using sequential tandem mass spectrometry. Anal Chem 1998; 70: 4951-9.
288. Delaney J, Vouros P. Liquid chromatography ion trap mass spectrometric analysis of oligosaccharides using permethylated derivatives. Rapid Commun Mass Spectrom 2001; 15: 325-34.
289. Shen X, Perreault H. Electrospray ionisation mass spectrometry of 1-phenyl-3-methyl-5-pyrazolone derivatives of neutral and N-acetylated oligosaccharides. J Mass Spectrom 1999; 34: 502-10.
290. Saba JA, Shen X, Jamieson JC, Perreault H. Effect of 1-phenyl-3-methyl-5-pyrazolone labeling on the fragmentation behavior of asialo and sialylated N-linked glycans under electrospray ionisation conditions. Rapid Commun Mass Spectrom 1999; 13: 704-11.
291. Saba JA, Shen X, Jamieson JC, Perreault H. Investigation of different combinations of derivatisation, separation methods and electrospray ionisation mass spectrometry for standard oligosaccharides and glycans from ovalbumin. J Mass Spectrom 2001; 36: 563-74.
292. Lattova E, Perreault H. Profiling of N-linked oligosaccharides using phenylhydrazine derivatisation and mass spectrometry. J Chromatogr A 2003; 1016: 71-87.
293. Suzuki S, Kakehi K, Honda S. Comparison of the sensitivities of various derivatives of oligosaccharides in LC/MS with fast atom bombardment and electrospray ionisation interfaces. Anal Chem 1996; 68: 2073-83.
294. Cancilla MT, Gaucher SP, Desaire H, Leary JA. Combined partial acid hydrolysis and electrospray ionisation-mass spectrometry for the structural determination of oligosaccharides. Anal Chem 2000; 72: 2901-7.
295. Wilson NL, Schulz BL, Karlsson NG, Packer NH. Sequential analysis of N- and O-linked glycosylation of 2D-PAGE separated glycoproteins. J Proteome Res 2002; 1: 521-9.
296. Håkansson K, Emmett MR, Marshall AG, Davidsson P, Nilsson C. Structural analysis of 2D-gel-separated glycoproteins from human cerebrospinal fluid by tandem high-resolution mass spectrometry. J Proteome Res 2003; 2: 581-8.
297. Charlwood J, Langridge J, Tolson D, Birrell H, Camilleri P. Profiling of 2-aminoacridone derivatised glycans by electrospray ionisation mass spectrometry. Rapid Commun Mass Spectrom 1999; 13: 107-12.
298. Charlwood J, Langridge J, Camilleri P. Structural characterisation of N-linked glycan mixtures by precursor ion scanning and tandem mass spectrometric analysis. Rapid Commun Mass Spectrom 1999; 13: 1522-30.
299. Harvey DJ. N-(2-diethylamino)ethyl-4-aminobenzamide derivative for high sensitivity mass spectrometric detection and structure determination of N-linked carbohydrates. Rapid Commun Mass Spectrom 2000; 14: 862-71.
300. Mo W, Sakamoto H, Nishikawa A, Kagi N, Langridge JI, Shimonishi Y, et al. Structural characterisation of chemically derivatised oligosaccharides by nanoflow electrospray ionisation mass spectrometry. Anal Chem 1999; 71: 4100-6.
301. Harvey DJ. Electrospray mass spectrometry and fragmentation of N-linked carbohydrates derivatised at the reducing terminus. J Am Soc Mass Spectrom 2000; 11: 900-15.
302. Harvey DJ. Collision-induced fragmentation of underivatised N-linked carbohydrates ionised by electrospray. J Mass Spectrom 2000; 35: 1178-90.
303. Wheeler SF, Harvey DJ. Negative ion mass spectrometry of sialylated carbohydrates: discrimination of N-acetylneuraminic acid linkages by MALDI-TOF and ESI-TOF mass spectrometry. Anal Chem 2000; 72: 5027-39.
304. Sagi D, Peter-Katalinic J, Conradt HS, Nimtz M. Sequencing of tri- and tetraantennary N-glycans containing sialic acid by negative mode ESI QTOF tandem MS. J Am Soc Mass Spectrom 2002; 13: 1138-48.
305. Thomsson KA, Karlsson H, Hansson GC. Sequencing of sulfated oligosaccharides from mucins by liquid chromatography and electrospray ionisation tandem mass spectrometry. Anal Chem 2000; 72: 4543-9.
306. Robbe C, Capon C, Coddeville B, Michalski JC. Diagnostic ions for the rapid analysis by nano-electrospray ionisation quadrupole time-of-flight mess spectrometry of O-glycans from human mucins. Rapid Commun Mass Spectrom 2004; 18: 412-420.
307. Bahr U, Pfenninger A, Karas M, Stahl B. High-sensitivity analysis of neutral underivatised oligosaccharides by nanoelectrospray mass spectrometry. Anal Chem 1997; 69: 4530-5.
308. Avci FY, Karst NA, Linhardt RJ. Synthetic oligosaccharides as heparin-mimetics displaying anticoagulant properties. Curr Pharm Design 2003; 9(28): 2323-35.
309. Elsinga PH, Hendrikse NH, Bart J, Vaalburg W, van Waarde A. PET Studies on P-glycoprotein function in the blood-brain barrier: how it affects uptake and binding of drugs within the CNS. Curr Pharm Design 2004; 10(13): 1493-503.
310. Wang LX. Bioorganic approaches towards HIV vaccine design. Curr Pharm Design 2003; 9(22): 1771-87.