Glycosylation analysis of proteins, proteoglycans, and glycolipids using capillary electrophoresis and mass spectrometry

Advances in Chromatography

Volumn 49, Issue , 2011, Pages 135-194

  Zamfir, Alina D ^a   Flangea, Corina ^a   Altmann, Friedrich ^b   Rizzi, Andreas M ^c  

^a AUREL VLAICU UNIVERSITY OF ARAD   (Romania)

^b UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOLIPID; GLYCOPROTEIN; PROTEOGLYCAN;

ANIMAL; CAPILLARY ELECTROPHORESIS; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY; MICROFLUIDIC ANALYSIS; PROCEDURES;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROPHORESIS, CAPILLARY; GLYCOLIPIDS; GLYCOPROTEINS; GLYCOSYLATION; HUMANS; MASS SPECTROMETRY; MICROFLUIDIC ANALYTICAL TECHNIQUES; PROTEOGLYCANS;

EID: 81155130103     PISSN: 00652415     EISSN: None     Source Type: Book Series    
DOI: 10.1201/b10721-5     Document Type: Article

References (279)

1. M. M. Fuster and J. D. Esko, The sweet and sour of cancer: glycans as novel therapeutic targets, Nat. Rev. Cancer 5: 526 (2005).
2. A. Varki, R. D. Cummings, J. D. Esko, H. Freeze, G. Hart and J. Marth, Essentials of Glycobiology, Cold Spring Harbor Laboratory Press, New York, pp. 537 (1999).
3. M. R. Bond and J. J. Kohler, Chemical methods for glycoprotein discovery, Curr. Opin. Chem. Biol. : 52 (2007).
4. Z. El Rassi, Carbohydrate Analysis by Modern Chromatography and Electrophoresis, in J.Chromatogr. Libr., Vol. 66, Elsevier, Amsterdam (2002).
5. H.-J. Gabius, The Sugar Code.Fundamentals in Glycosciences, Wiley-Blackwell, Weinheim (2009).
6. C. Huhn, M. H. J. Selman, L. R. Ruhaak, A. M. Deelder and M. Wuhrer, IgG glycosylation analysis, Proteomics, 9: 882 (2009).
7. P. J. Domann, A. C. Pardos-Pardos, D. L. Fernandes, D. I. R. Spencer, C. M. Radcliff, L. Royle, R. A. Dwek and P. M. Rudd, Separation-based glycoprofiling approaches using fluorescent labels, Practical Proteomics, 2: 70 (2007).
8. Y. Mechref and M. V. Novotny, Structural investigations of glycoconjugates at high sensitivity, Chem. Rev., 102: 321 (2002).
9. S. Amon, A. D. Zamfir and A. Rizzi, Glycosylation analysis of glycoproteins and proteoglycans using capillary electrophoresis-mass spectrometry strategies, Electrophoresis, 29: 2485 (2008).
10. C. Campa, A. Coslovi, A. Flamigni and M. Rossi, Overview on advances in capillary electrophoresis-mass spectrometry of carbohydrates: A tabulated review, Electrophoresis, 27: 2027 (2006).
11. A. Zamfir and J. Peter-Katalinic, Capillary electrophoresis-mass spectrometry for glycoscreening in biomedical research, Electrophoresis, 25: 1949 (2004).
12. W. Morelle, K. Canis, F. Chirat, V. Faid and J.-C. Michalski, Characterization of N-glycans of recombinant human thyrotropin using mass spectrometry, Proteomics, 6: 3993 (2006).
13. W. Morelle and J.-C. Michalski, The mass spectrometric analysis of glycoproteins and their glycan structures., Curr. Anal. Chem., 1: 29 (2005).
14. W. Morelle and J.-C. Michalski, Sequencing of oligosaccharides derivatized with benzylamine using electrospray ionization-quadrupole time of flight-tandem mass spectrometry, Electrophoresis 25: 2144 (2004).
15. Y. Mechref and M. V. Novotny, Chem. Rev., 102: 321 (2002).
16. M. Stahl, A. Von Brocke and E. Bayer, in Carbohydrate Analysis by Modern Chromatography and Electrophoresis, Vol. 66, Z. El Rassi, Ed., Elsevier, Amsterdam, pp. 961 (2002).
17. D. J. Harvey, Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates, Mass Spectrom. Rev., 18: 349 (1999).
18. R. Schwartz-Albiez, in The Sugar Code.Fundamentals of Glycosciences, H.-J. Gabius, Ed., Wiley- Blackwell, Weinheim, 2009, p. 447.
19. T. Hennet, in The Sugar Code.Fundamentals of Glycosciences, H.-J. Gabius, Ed., Wiley- Blackwell, Weinheim, 2009, p. 365.
20. F. A. Habermann and F. Sinowatz, in The Sugar Code.Fundamentals of Glycosciences, H.-J. Gabius, Ed., Wiley-Blackwell, Weinheim, 2009, p. 403.
21. R. W. Ledeen and G. Wu, in The Sugar Code.Fundamentals of Glycosciences, H.-J. Gabius, Ed., Wiley-Blackwell, Weinheim, 2009, p. 495.
22. K. Honke and N. Taniguchi, in The Sugar Code.Fundamentals of Glycosciences, H.-J. Gabius, Ed., Wiley-Blackwell, Weinheim, 2009, p. 385.
23. A. J. McCoy, X. Y. Pei, R. Skinner, J.-P. Abrahams and R. W. Carrell, Structure of beta- Antithrombin and the effect of glycosylation on antithrombin's heparin affinity and activity, J. Mol. Biol., 326: 823 (2003).
24. B. Turk, I. Brieditis, S. C. Bock, S. T. Olson and I. Bjork, The oligosaccharide side chain on Asn- 135 of alpha-antithrombin, absent in beta-antithrombin, decreases the heparin affinity of the inhibitor by affecting the heparin-induced conformational change, Biochemistry, 36: 6682 (1997).
25. A. Plematl, U. M. Demelbauer, D. Josi. and A. Rizzi, Determination of the site-specific and isoform-specific glycosylation in human plasma-derived antithrombin by IEF and capillary HPLC- ESI-MS/MS, Proteomics, 5: 4026 (2005).
26. T. Edmunds, S. M. Van Patten, J. Pollock, E. Hanson, R. Bernasconi, E. Higgins, P. Manavalan, C. Ziomek, H. Meade, J. M. McPherson and E. S. Cole, Transgenically produced human antithrombin: structural and functional comparison to human plasma-derived antithrombin, Blood, 91: 4561 (1998).
27. L. Garone, T. Edmunds, E. Hanson, R. Bernasconi, J. A. Huntington, J. L. Meagher, B. Fan and P. G. W. Gettins, Biochemistry, 35: 8881 (1996).
28. R. Jefferis, Glycosylation as a strategy to improve antibody-based therapeutics, Nat Rev Drug Discov., 8: 226 (2009).
29. J. Peter-Katalinic, O-glycosylation of proteins, Methods in Enzymology, 405: 139 (2005).
30. J. Zaia, Mass spectrometry of oligosaccharides, Mass. Spectrom. Rev., 23: 161 (2004).
31. M. Wuhrer, M. I. Catalina, A. M. Deelder and C. H. Hokke, Glycoproteomics based on tandem mass spectrometry of glycopeptides, J. Chromatogr. B n Anal.Techn. Biomed. Life Sci., 849: 115 (2007).
32. Z. Yang, W. S. Hancock, T. R. Chew and L. Bonilla, Proteomics, 5: 3353 (2005).
33. R. Qiu and F. E. Regnier, Anal. Chem., 77: 7225 (2005).
34. J. Hirabayasi and K.-I. Kasai, Separation technologies for glycomics, J. Chromatogr. B, 771: 67 (2002).
35. M. Geng, X. Zhang, M. Bina and F. Regnier, Proteomics of glycoproteins based on affinity selection of glycopeptides from tryptic digests, Journal of Chromatography B: Biomedical Sciences and Applications, 752: 293 (2001).
36. Z. Xu, X. Zhou, H. Lu, N. Wu, H. Zhao, L. Zhang, W. Zhang, Y. L. Liang, L. Wang, Y. Liu, P. Yang and X. Zha, Proteomics, 7: 2358 (2007).
37. T. Schwientek, U. Mandel, U. Roth, S. Mueller and F.-G. Hanisch, Proteomics 7: 3264 (2007).
38. T. Endo, in Carbohydrate Analysis by Modern Chromatography and Electrophoresis, Elsevier Science B.V., 2002, p. 251.
39. A. Monzo, G. K. Bonn and A. Guttman, Lectin-immobilization strategies for affinity purification and separation of glycoconjugates, TrAC, 26: 423 (2007).
40. A. Monzo, M. Olajos, L. De Benedictis, Z. Rivera, G. K. Bonn and A. Guttman, Boronic acid lectin affinity chromatography (BLAC). 2. Affinity micropartitioning-mediated comparative glycosylation profiling, Anal. Bioanal. Chem., 392: 195 (2008).
41. N. L. Wilson, N. G. Karlsson and N. H. Packer, Enrichment and analysis of glycoproteins in the proteome, in Separation Methods in Proteomics, G. B. Smejkal, and A. Lazareu, Eds., CRC Press LLC, Boca Raton, Fla (2006).
42. K. Yamamoto, T. Tsuji and T. Osawa, in Protein Protocols Handbook, J. M. Walker, Ed., Humana Press Inc., Totowa, N. J 2002, p. 917.
43. K. Niikura, R. Kamitani, M. Kurogochi, R. Uematsu, Y. Shinohara, H. Nakagawa, K. Deguchi, K. Monde, H. Kondo and S.-I. Nishimura, Versatile glycoblotting nanoparticles for high-throughput protein glycomics, Chem. Eur. J., 11: 3825 (2005).
44. H. Zhang, X.-J. Li, D. B. Martin and R. Aebersold, Identification and quantification of N-linked glycoproteins using hydrazide chemistry, stable isotope labeling and mass spectrometry, Nature Biotechnology, 21: 660 (2003).
45. H. Zhang and R. Aebersold, in Methods in Molecular Biology.New and Emerging Proteomic Techniques, Vol. 328, Humana Press Inc., Totowa, NJ, USA 2006, p. 177.
46. B. Wollscheid, D. Bausch-Fluck, C. Henderson, R. O'Brien, M. Bibel, R. Schiess, R. Aebersold and J. D. Watts, Mass-spectrometric identification and relative quantification of N-linked cell surface glycoproteins, Nat Biotechnol., 27: 378 (2009).
47. R. Nuck, M. Zimmermann, D. Sauvageot, D. Josi and W. Reutter, Optimized deglycosylation of glycoproteins by peptide-N4-(N-acetyl-beta-glucosaminyl)-asparagine amidase from Flavobacterium meningosepticum, Glycoconj. J., 7: 279 (1990).
48. V. Tretter, F. Altmann and L. Marz, 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., 199: 647 (1991).
49. M. M. Brooks and A. V. Savage, The substrate specificity of the enzyme endo-alpha-N-acetyl-D- galactosaminidase from Diplococcus pneumonia, Glycoconj. J., 14: 183 (1997).
50. L. Royle, T. S. Mattu, E. Hart, J. I. Langridge, A. H. Merry, N. Murphy, D. J. Harvey, R. A. Dwek and P. M. Rudd, An analytical and structural database provides a strategy for sequencing O- glycans from microgram quantities of glycoproteins, Anal. Biochem., 304: 70 (2002).
51. B. L. Schulz, A. J. Sloane, L. J. Robinson, S. S. Prasad, R. A. Lindner, M. Robinson, P. T. Bye, D. W. Nielson, J. L. Harry, N. H. Packer and N. G. Karlsson, Glycosylation of sputum mucins is altered in cystic fibrosis patients, Glycobiology, 17: 698 (2007).
52. J. Gonzales, T. Takao, H. Hori, V. Besada, R. Rodriguez, G. Padron and Y. Shimonishi, A method for determination of N-glycosylation sites in glycoproteins by collision-induced dissociation analysis in fast atom bombardment mass spectrometry: identification of the positions of carbohydrate-linked asparagine in recombinant alpha-amylase by treatment with peptide-N- glycosidase F in 18O-labeled water, Anal.Biochem., 205: 151 (1992).
53. L. Xiong and F. E. Regnier, Use of a lectin affinity selector in the search for unusual glycosylation in proteomics, J. Chromatogr. B n Anal. Technol. Biomed. Life Sci. 782: 405 (2002).
54. L. Ruhaak, C. Huhn, W. J. Waterreus, A. R. de Boer, C. Neusus, C. Hokke, A. M. Deelder and M. Wuhrer, Hydrophilic interaction chromatography-based high-throughput sample preparation method for N-glycan analysis from total human plasma glycoproteins, Anal. Chem., 80: 6119 (2008).
55. N. G. Karlsson, N. L. Wilson, H.-J. Wirth, P. Dawes, J. Hiren and N. H. Packer, Negative ion graphitised carbon nano-liquid chromatography/mass spectrometry increases sensitivity for glycoprotein oligosaccharide analysis Rapid Commun. Mass Spectrom, 18: 2282 (2004).
56. P. J. Domann, A. C. Pardos-Pardos, D. L. Fernandes, D. I. R. Spencer, C. M. Radcliffe, L. Royle, R. A. Dwek and P. M. Rudd, Separation-based glycoprofiling approaches using fluorescent labels, Proteomics, 7: 70 (2007).
57. E. Sisu, W. T. Bosker, W. Norde, T. M. Slaghek, J. W. Timmermans, J. Peter-Katalini., M. A. Cohen-Stuart and A. D. Zamfir, Electrospray ionization quadrupole time-of-flight tandem mass spectrometric analysis of hexamethylenediamine-modified maltodextrin and dextran,, Rapid Commun. Mass Spectrom., 20: 209 (2006).
58. F. N. Lamari, R. Kuhn and N. K. Karamanos, Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis, J. Chromatogr. B 793: 15 (2003).
59. P. Kang, Y. Mechref, I. Klouckova and M. V. Novotny, Solid-phase permethylation of glycans for mass spectrometric analysis, Rapid Commun. Mass Spectrom., 19: 3421 (2005).
60. Y. Mechref, P. Kang and M. V. Novotny, Differentiating structural isomers of sialylated glycans by matrix-assisted laser desorption/ionization time-of-flight/time-of-flight tandem mass spectrometry, Rapid Commun. Mass Spectrom., 20: 1381 (2006).
61. Y. Mechref and M. V. Novotny, Glycomic analysis by capillary electrophoresis-mass spectrometry, Mass Spectrom. Rev., 28: 207 (2009).
62. S. J. North, P. G. Hitchen, S. M. Haslam and A. Dell, Mass spectrometry in the analysis of N- linked and O-linked glycans, Curr. Opin. Struct. Biol., 19: 498 (2009).
63. V. N. Reinhold, B. B. Reinhold and C. E. Costello, Carbohydrate molecular weight profiling, sequence, linkage, and branching data: ES-MS and CID, Anal. Chem., 67: 1772 (1995).
64. C. E. Costello, J. M. Contado-Miller and J. F. Cipollo, A glycomic platform for the analysis of permethylated oligosaccharide alditols, J. Am. Soc. Mass Spectrom., 18: 1799 (2007).
65. F. Benavente, M. C. Vescina, E. Hernandez, V. Sanz-Nebot, J. Barbosa and N. A. Guzman, Lowering the concentration limits of detection by on-line solid-phase extraction-capillary electrophoresis-electrospray mass spectrometry, J. Chromatogr. A 1140: 205 (2007).
66. F. Benavente, E. Hernandez, N. A. Guzman, V. Sanz-Nebot and J. Barbosa, Determination of human erythropoietin by on-line immunoaffinity capillary electrophoresis: A preliminary report, Anal. Bioanal. Chem., 387: 2633 (2007).
67. N. A. Guzman and T. M. Phillips, Immunoaffinity capillary electrophoresis for proteomics studies Anal. Chem., 77: 60A (2005).
68. N. A. Guzman, T. Blanc and T. M. Phillips, Immunoaffinity capillary electrophoresis as a powerful strategy for the quantification of low-abundance biomarkers, drugs, and metabolites in biological matrices, Electrophoresis 29: 3259 (2008).
69. A. von Brocke, G. Nicholson and E. Bayer, Recent advances in capillary electrophoresis/electrospray-mass spectrometry, Electrophoresis, 22: 1251 (2001).
70. G. M. Janini, M. Zhou, L. R. Yu, J. Blonder, M. Gignac, T. P. Conrads, H. J. Issaq and T. D. Veenstra, On-column sample enrichment for capillary electrophoresis sheathless electrospray ionization mass spectrometry: evaluation for peptide analysis and protein identification, Anal. Chem., 75: 5984 (2003).
71. J. Hernandez-Borges, C. Neususs, A. Cifuentes and M. Pelzing, On-line capillary electrophoresis-mass spectrometry for the analysis of biomolecules, Electrophoresis, 25: 2257 (2004).
72. P. Schmitt-Kopplin and M. Englmann, Capillary electrophoresis.mass spectrometry: survey on developments and applications 2003-2004, Electrophoresis, 26: 1209 (2005).
73. H. Stutz, Advances in the analysis of proteins and peptides by capillary electrophoresis with matrix-assisted laser desorption/ionization and electrospray-mass spectrometry detection, Electrophoresis, 26: 1254 (2005).
74. Z. Kele, G. Ferenc, E. Klement, G. K. Toth and T. Janaky, Design and performance of a sheathless capillary electrophoresis/mass spectrometry interface by combining fused-silica capillaries with gold-coated nanoelectrospray tips, Rapid Commun. Mass Spectrom., 19: 881 (2005).
75. A. D. Zamfir, N. Dinca, E. Sisu and J. Peter-Katalinic, Copper-coated microsprayer interface for on-line sheathless capillary electrophoresis electrospray mass spectrometry of carbohydrates, J. Sep. Sci., 29: 414 (2006).
76. Y. Z. Chang and G. R. Her, Sheathless capillary electrophoresis/electrospray mass spectrometry using a carbon-coated fused-silica capillary, Anal. Chem., 72: 626 (2000).
77. A. D. Zamfir, D. G. Seidler, E. Schonherr, H. Kresse and J. Peter-Katalinic, On-line sheathless capillary electrophoresis/nanoelectrospray ionization-tandem mass spectrometry for the analysis of glycosaminoglycan oligosaccharides, Electrophoresis, 25: 2010 (2004).
78. J. T. Whitt and M. Moini, Capillary Electrophoresis to Mass Spectrometry Interface Using a Porous Junction, Anal. Chem., 75: 2188 (2003).
79. M. Moini, Design and performance of a universal sheathless capillary electrophoresis to mass spectrometry interface using a split-flow technique, Anal. Chem., 73: 3497 (2001).
80. M. Moini, Capillary electrophoresis mass spectrometry and its application to the analysis of biological mixtures, Anal. Bioanal. Chem., 373: 466 (2002).
81. M. Moini, Simplifying CE-MS operation. 2. Interfacing low-flow separation techniques to mass spectrometry using a porous tip, Anal. Chem., 79: 4241 (2007).
82. M. Moini, in Methods in Molecular Biology Vol. 276 (Capillary Electrophoresis of Proteins and Peptides), Humana Press Inc., Totowa, NJ, United States, 2004, p. 253.
83. S. Garza and M. Moini, Analysis of Complex Protein Mixtures with Improved Sequence Coverage Using (CE-MS/MS)n, Anal. Chem., 78: 7309 (2006).
84. M. C. Tseng, Y. R. Chen and G. R. Her, A low-makeup beveled tip capillary electrophoresis/electrospray ionization mass spectrometry interface for micellar electrokinetic chromatography and nonvolatile buffer capillary electrophoresis, Anal. Chem., 76: 6306 (2004).
85. T. Johnson, J. Bergquist, R. Ekman and E. Nordhoff, A CE-MALDI interface based on the use of prestructured sample supports, Anal. Chem., 73: 1670 (2001).
86. A. Zuberovic, M. Wetterhall, J. Hanrieder and J. Bergquist, MALDI-TOF/TOF MS for multiplexed quantification of proteins in human ventricular cerebrospinal fluid, Electrophoresis 30: 1836 (2009).
87. J.-M. Busnel, J. Josserand, N. Lion and H. H. Girault, Iontophoretic Fraction Collection for Coupling Capillary Zone Electrophoresis with Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry, Anal. Chem., 81: 3867 (2009).
88. O. Muller, F. Foret and B. L. Karger, Design of a high-precision fraction collector for capillary electrophoresis, Anal. Chem., 67: 2974 (1995).
89. J. Preisler, P. Hu, T. Rejtar, E. Moskovets and B. L. Karger, Capillary array electrophoresis- MALDI mass spectrometry using a vacuum deposition interface, Anal. Chem., 74: 17 (2002).
90. H. Zhang and K. K. C. Yeung, Nanoliter-volume selective sampling of peptides based on isoelectric points for MALDI-MS, Anal. Chem., 76: 6814 (2004).
91. C. W. Huck, R. Bakry, L. A. Huber and G. K. Bonn, Progress in capillary electrophoresis coupled to matrix-assisted laser desorption/ionization-time of flight mass spectrometry, Electrophoresis, 27: 2063 (2006).
92. Y. Luo, S. Xu, J. W. Schilling, K. H. Lau, J. C. Whitin, T. T. S. Yu and H. J. Cohen, Microfluidic device for coupling capillary electrophoresis and matrix-assisted laser desorption ionization-mass spectrometry, JALA 14: 252 (2009).
93. S. Amon, A. Plematl and A. Rizzi, Capillary zone electrophoresis of glycopeptides under controlled electroosmotic flow conditions coupled to electrospray and matrix-assisted laser desorption/ionization mass spectrometry, Electrophoresis, 27: 1209 (2006).
94. M. Lechner, A. Seifner and A. Rizzi, Capillary isoelectric focusing hyphenated to single- And multistage MALDI-mass spectrometry using automated sheath-flow assisted sample deposition, Electrophoresis, 29: 1974 (2008).
95. G. Choudhary, J. Chakel, W. Hancock, A. Torres-Duarte, G. McMahon and I. Wainer, Investigation of the potential of capillary electrophoresis with off-line matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for clinical analysis: Examination of a glycoprotein factor associated with cancer cachexia, Anal. Chem., 71: 855 (1999).
96. H. Suzuki, O. Mueller, A. Guttman and B. L. Karger, Analysis of 1-aminopyrene-3, 6, 8- Trisulfonate-derivatized oligosaccharides by capillary electrophoresis with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, Anal. Chem., 69: 4554 (1997).
97. H. J. An, A. H. Franz and C. B. Lebrilla, Improved capillary electrophoretic separation and mass spectrometric detection of oligosaccharides, J. Chromatogr. A, 1004: 121 (2003).
98. S. I. Snovida, V. C. Chen, O. Krokhin and H. Perreault, Isolation and identification of sialylated glycopeptides from bovine a1-acid glycoprotein by off-line capillary electrophoresis MALDI-TOF mass spectrometry, Anal. Chem., 78: 6556 (2006).
99. S. J. North, P. G. Hitchen, S. M. Haslam and A. Dell, Mass spectrometry in the analysis of N- linked and O-linked glycans, Curr. Opin. Struct. Biol., 19: 498 (2009).
100. J. J. Wolff, I. J. Amster, L. Chi and R. J. Linhardt, Electron detachment dissociation of glycosaminoglycan tetrasaccharides, J. Am. Soc. Mass Spectrom., 18: 234 (2007).
101. F. E. Leach, J. J. Wolff, T. N. Laremore, R. J. Linhardt and I. J. Amster, Evaluation of the experimental parameters which control electron detachment dissociation, and their effect on the fragmentation efficiency of glycosaminoglycan carbohydrates, Int. J. Mass Spectrom., 276: 110 (2008).
102. J. J. Wolff, T. N. Laremore, A. M. Busch, R. J. Linhardt and I. J. Amster, Electron detachment dissociation of dermatan sulfate oligosaccharides, J. Am. Soc. Mass Spectrom., 19: 294 (2008).
103. J. J. Wolff, T. N. Laremore, A. M. Busch, R. J. Linhardt and I. J. Amster, Influence of charge state and sodium cationization on the electron detachment dissociation and infrared multiphoton dissociation of glycosaminoglycan oligosaccharides, J. Am. Soc. Mass Spectrom., 19: 790 (2008).
104. G. C. Gil, W. H. Velander and K. E. Van Cott, N-glycosylation microheterogeneity and site occupancy of an Asn-X-Cys sequon in plasma-derived and recombinant protein C, Proteomics, 9: 2555 (2009).
105. J. F. Valliere-Douglass, P. Kodama, M. Mujacic, L. Brady, W. Wang, A. Wallace, B. Yan, P. Reddy, M. J. Treuheit and A. Balland, Asparagine-linked oligosaccharides present on a non- consensus amino acid sequence in the CH1 domain of human antibodies, J. Biol. Chem., 284: 32493 (2009).
106. S. Kamoda and K. Kakehi, Evaluation of glycosylation for quality assurance of antibody pharmaceuticals by capillary electrophoresis, Electrophoresis, 29: 3595 (2008).
107. C. Neususs and M. Pelzing, in Methods in Molecular Biology (Mass Spectrometry of Proteins and Peptides), Vol. 492, Humana Press Inc., Totowa, NJ, United States, 2009, p. 201.
108. H. Stutz, Protein attachment onto silica surfaces.a survey of molecular fundamentals, resulting effects and novel preventive strategies in CE, Electrophoresis, 30: 2032 (2009).
109. U. M. Demelbauer, A. Plematl, L. Kremser, G. Allmaier, D. Josic and A. Rizzi, Characterization of glyco isoforms in plasma-derived human antithrombin by on-line capillary zone electrophoresis-electrospray ionization-quadrupole ion trap-mass spectrometry of the intact glycoproteins, Electrophoresis, 25: 2026 (2004).
110. V. Sanz-Nebot, E. Balaguer, F. Benavente, C. Neusüß and J. Barbosa, Characterization of transferrin glycoforms in human serum by CE-UV and CE-ESI-MS, Electrophoresis, 28: 1949 (2007).
111. E. Balaguer and C. Neusüß, Glycoprotein characterization combining intact protein and glycan analysis by capillary electrophoresis-electrospray ionization-mass spectrometry, Anal. Chem., 78: 5384 (2006).
112. E. Balaguer and C. Neusüß, Intact glycoform characterization of erythropoietin-? and erythropoietin-? by CZE-ESI- TOF-MS, Chromatographia, 64: 351 (2006).
113. E. Balaguer, U. Demelbauer, M. Pelzing, V. Sanz-Nebot, J. Barbosa and C. Neusüß, Glycoform characterization of erythropoietin combining glycan and intact protein analysis by capillary electrophoresis-Electrospray-time-of-flight mass spectrometry, Electrophoresis, 27: 2638 (2006).
114. B. Yu, H. Cong, H. Liu, Y. Li and F. Liu, Ionene-dynamically coated capillary for analysis of urinary and recombinant human erythropoietin by capillary electrophoresis and online electrospray ionization mass spectrometry, J. Sep. Sci., 28: 2390 (2005).
115. C. Neusuess, U. Demelbauer and M. Pelzing, Glycoform characterization of intact erythropoietin by capillary electrophoresis-electrospray-time of flight-mass spectrometry, Electrophoresis, 26: 1442 (2005).
116. C. Neusüß, U. Demelbauer and M. Pelzing, Glycoform characterization of intact eryth-ropoietin by capillary electrophoresis-electrospray-time of flight-mass spectrometry, Electrophoresis, 26: 1442 (2005).
117. E. Gimenez, F. Benavente, J. Barbosa and V. Sanz-Nebot, Analysis of intact erythropoietin and NESP by CE- electrspray- ion trap MS, Electrophoresis, 29: 2161 (2008).
118. A. Puerta and J. Bergquist, Development of a CE-MS method to analyze components of the potential biomarker vascular endothelial growth factor 165, Electrophoresis, 30: 2355 (2009).
119. D. Thakur, T. Rejtar, B. L. Karger, N. J. Washburn, C. J. Bosques, N. S. Gunay, Z. Shriver and G. Venkataraman, Profiling of glycoforms of the intact alpha-subunit of recombinant human choronic gonadotropin by high-resolution capillary electrophoresis-mass spectrometry, Anal. Chem., 81: 899 (2009).
120. Y. Zheng, H. Li, Z. Guo, J.-M. Lin and Z. Cai, Chip-based CE coupled to a quadrupole TOF mass spectrometer for the analysis of a glycopeptide, Electrophoresis, 28: 1305 (2007).
121. B. Domon and C. E. Costello, A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates, Glycoconj. J., 5: 397 (1988).
122. L. Bindila, R. Almeida, A. Sterling, M. Allen, J. Peter-Katalinic and A. Zamfir, Off-line capillary electrophoresis/fully automated nanoelectrospray chip quadrupole time-of-flight mass spectrometry and tandem mass spectrometry for glycoconjugate analysis, J. Mass Spectrom., 39: 1190 (2004).
123. M. Wuhrer, J. C. Stam, F. E. van de Geijn, C. A. Koeleman, C. T. Verrips, R. J. Dolhain, C. H. Hokke and A. M. Deelder, Glycosylation profiling of immunoglobulin G (IgG) subclasses from human serum, Proteomics, 7: 4070 (2007).
124. L. A. Gennaro, O. Salas-Solano and S. Ma, Capillary electrophoresis-mass spectrometry as a characterization tool for therapeutic proteins, Anal. Biochem., 355: 249 (2006).
125. E. Bonneil, N. M. Young, H. Lis, N. Sharon and P. Thibault, Probing genetic variation and glycoform distribution in lectins of the Erythrina genus by mass spectrometry, Arch. Biochem. Biophys., 426: 241 (2004).
126. J. Li, J. F. Kelly, I. Chemushevich, D. J. Harrison and P. Thibault, Separation and identification of peptides from gel-isolated membrane proteins using a microfabricated device for combined capillary electrophoresis/nanoelectrospray mass spectrometry, Anal. Chem., 72: 599 (2000).
127. T. Liu, J.-D. Li, R. Zeng, X.-X. Shao, K.-Y. Wang and Q.-C. Xia, Capillary electrophoresis-electrospray mass spectrometry for the characterization of high-mannose-type N-glycosylation and differential oxidation in glycoproteins by charge reversal and protease/glycosidase digestion, Anal. Chem., 73: 5875 (2001).
128. K. Sandra, F. Lynen, B. Devreese, J. Van Beeumen and P. Sandra, On-column sample enrichment for the high- sensitivity sheath-flow CE-MS analysis of peptides, Anal. Bioanal. Chem., 385: 671 (2006).
129. C.-C. Lai and G.-R. Her, Analysis of phospholipase A2 glycosylation patterns from venom of individual bees by capillary electrophoresis/electrospray ionization mass spectrometry using an ion trap mass spectrometer, Rapid Commun. Mass Spectrom., 14: 2012 (2000).
130. A. Zamfir and J. Peter-Katalinic, Glycoscreening by on-line sheathless capillary electro-phoresis/electrospray ionization-quadrupole time of flight-tandem mass spectrometry, Electrophoresis, 22: 2448 (2001).
131. A. Zamfir, S. König, J. Althoff and J. Peter-Katalinc, Capillary electrophoresis and off-line capillary electrophoresis- electrospray ionization quadrupole time-of-flight tandem mass spectrometry of carbohydrates, J. Chromatogr. A, 895: 291 (2000).
132. L. Bindila, J. Peter-Katalinic and A. Zamfir, Sheathless reverse-polarity capillary electrophoresis-electrospray-mass spectrometry for analysis of underivatized glycoconjugates, Electrophoresis, 26: 1488 (2005).
133. Z. El Rassi, in Adv. in Chromatogr., Vol. 34, P. R. Brown, and E. Grushka, Eds., Marcel Dekker, New York, 1994, p. 177.
134. Z. El Rassi, Recent developments in capillary electrophoresis and capillary electrochromatography of carbohydrate species, Electrophoresis, 20: 3134 (1999).
135. A. Guttman, F.-T. A. Chen and R. A. Evangelista, High-resolution capillary gel electrophoresis of reducing oligosaccharides labeled with 1-aminopyrene-3, 6, 8-trisulfonate, Anal. Biochem., 233: 234 (1996).
136. N. Callewaert, G. Geysens, F. Molemans and R. Contreras, Ultrasensitive profiling and sequencing of N-linked oligosaccharides using standard DNA-sequencing equipment, Glycobiology, 11: 275 (2001).
137. N. Callewaert, R. Contreras, L. Mitnik-Gankin, L. Carey, P. Matsudaira and D. Ehrlich, Total serum protein N- glycome profiling on a CE-microfluidics platform, Electrophoresis, 25 (2004).
138. W. Laroy, R. Contreras and N. Callewaert, Glycome mapping on DNA sequencing equipment, Nature protocols, 1: 397 (2006).
139. J. Schwarzer, E. Rapp and U. Reichl, N-glycan analysis by CGE-LIF: profiling influenza A virus hemagglutinin N-glycosylation during vaccine production, Electrophoresis, 29: 4203 (2008).
140. J. B. Briggs, R. G. Keck, S. Ma, W. Lau and A. J. S. Jones, An analytical system for the characterization of highly heterogeneous mixtures of N-linked oligosaccharides, Anal. Biochem., 389: 40 (2009).
141. L. A. Gennaro, J. Delaney, P. Vouros, D. J. Harvey and B. Domon, Capillary electro-phoresis/electrospray ion trap mass spectrometry for the analysis of negatively charged derivatized and underivatized glycans, Rapid Commun. Mass Spectrom., 16: 192 (2002).
142. M. A. Kabel, W. H. Heijnis, E. J. Bakx, R. Kuijpers, A. G. J. Voragen and H. A. Schols, Capillary electrophoresis fingerprinting, quantification and mass-identification of various 9-aminopyrene-1, 4, 6-trisulfonate-derivatized oligomers derived from plant polysaccharides, J. Chromatogr. A 1137: 119 (2006).
143. M. Nakano, D. Higo, E. Arai, T. Nakagawa, K. Kakehi, N. Taniguchi and A. Kondo, Capillary electrophoresis- electrospray ionization mass spectrometry for rapid and sensitive N-glycan analysis of glycoproteins as 9-fluorenylmethyl derivatives, Glycobiology, 19: 135 (2009).
144. M. V. Novotny, Glycoconjugate analysis by capillary electrophoresis, Methods in Enzymology, 271: 319 (1996).
145. Y. Mechref, J. Muzikar and M. V. Novotny, Comprehensive assessment of N-glycans derived from a murine monoclonal antibody: A case for multimethodological approach, Electrophoresis 26: 2034 (2005).
146. M. Wuhrer, A. M. Deelder and C. H. Hokke, Protein glycosylation analysis by liquid chromatography-mass spectrometry, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 825: 124 (2005).
147. S. Hase, T. Ibuki and T. Ikenaka, Reexamination of the pyridylamination used for fluo-rescence labeling of oligosaccharides and its application to glycoproteins, J. Biochem., 95: 197 (1984).
148. S. Natsuka, S. Hase and T. Ikenaka, Fluorescence method for the structural analysis of oligomannose-type sugar chains by partial acetolysis, Anal. Biochem., 167: 154 (1987).
149. N. Tomiya, J. Awaya, M. Kurono, S. Endo, Y. Arata and N. Takahashi, Analyses of N-linked oligosaccharides using a two-dimensional mapping technique, Anal. Biochem., 171: 73 (1988).
150. M. J. Davies and E. F. Hounsell, Comparison of separation modes of high-performance liquid chromatography for the analysis of glycoprotein- And proteoglycan-derived oli-gosaccharides, J. Chromatogr. A, 720: 227 (1996).
151. M. Pabst, D. Kolarich, G. Poltl, T. Dalik, G. Lubec, A. Hofinger and F. Altmann, Comparison of fluorescent labels for oligosaccharides and introduction of a new postlabeling purification method, Anal. Biochem., 384: 263 (2009).
152. K. R. Anumula, Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates, Anal. Biochem., 350: 1 (2006).
153. P. Hermentin, R. Witzel, J. F. Vliegenthart, J. P. Kamerling, M. Nimtz and H. S. Conradt, A strategy for the mapping of N-glycans by high-pH anion-exchange chromatography with pulsed amperometric detection, Anal. Biochem., 203: 281 (1992).
154. M. P. Gillmeister, N. Tomiya, S. J. Jacobia, Y. C. Lee, S. F. Gorfien and M. J. Betenbaugh, An HPLC-MALDI MS method for N-glycan analyses using smaller size samples: Application to monitor glycan modulation by medium conditions, Glycoconj. J., 26: 1135 (2009).
155. S. Maslen, P. Sadowski, A. Adam, K. Lilley and E. Stephens, Differentiation of isomeric N-glycan structures by normal-phase liquid chromatography-MALDI-TOF/TOF tandem mass spectrometry, Anal. Chem., 78: 8491 (2006).
156. C. Bruggink, R. Maurer, H. Herrmann, S. Cavalli and F. Hoefler, Analysis of carbohydrates by anion exchange chromatography and mass spectrometry, J. Chromatogr. A, 1085: 104 (2005).
157. C. Bruggink, M. Wuhrer, C. A. Koeleman, V. Barreto, Y. Liu, C. Pohl, A. Ingendoh, C. H. Hokke and A. M. Deelder, Oligosaccharide analysis by capillary-scale high-pH anion-exchange chromatography with on-line ion-trap mass spectrometry, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 829: 136 (2005).
158. G. Chataigne, F. Couderc and V. Poinsot, Polysaccharides analysis of sinorhizobial capside by on-line anion exchange chromatography with pulsed amperometric detection and mass spectrometry coupling, J. Chromatogr. A, 1185: 241 (2008).
159. T. L. Delatte, M. H. Selman, H. Schluepmann, G. W. Somsen, S. C. Smeekens and G. J. de Jong, Determination of trehalose-6-phosphate in Arabidopsis seedlings by successive extractions followed by anion exchange chromatography- mass spectrometry, Anal. Biochem., 389: 12 (2009).
160. S. Hase, Precolumn derivatization for chromatographic and electrophoretic analyses of carbohydrates, J. Chromatogr. A, 720: 137 (1996).
161. N. Takahashi, H. Nakagawa, K. Fujikawa, Y. Kawamura and N. Tomiya, Three-dimensional elution mapping of pyridylaminated N-linked neutral and sialyl oligosaccharides, Anal. Biochem., 226: 139 (1y995).
162. Y. Takegawa, K. Deguchi, S. Ito, S. Yoshioka, A. Sano, K. Yoshinari, K. Kobayashi, H. Nakagawa, K. Monde and S. Nishimura, Assignment and quantification of 2-aminopyridine derivatized oligosaccharide isomers coeluted on reversed-phase HPLC/MS by MSn spectral library, Anal. Chem., 76: 7294 (2004).
163. H. Nakagawa, M. Hato, Y. Takegawa, K. Deguchi, H. Ito, M. Takahata, N. Iwasaki, A. Minami and S. Nishimura, Detection of altered N-glycan profiles in whole serum from rheumatoid arthritis patients, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 853: 133 (2007).
164. Y. Kanie, M. Yamamoto-Hino, Y. Karino, H. Yokozawa, S. Nishihara, R. Ueda, S. Goto and O. Kanie, Insight into the regulation of glycan synthesis in Drosophila chaoptin based on mass spectrometry, PLoS One, 4: e5434 (2009).
165. L. A. Gennaro, D. J. Harvey and P. Vouros, Reversed-phase ion-pairing liquid chroma-tography/ion trap mass spectrometry for the analysis of negatively charged, derivatized glycans, Rapid Commun. Mass Spectrom., 17: 1528 (2003).
166. X. Chen and G. C. Flynn, Analysis of N-glycans from recombinant immunoglobulin G by on-line reversed-phase high-performance liquid chromatography/mass spectrometry, Anal. Biochem., 370: 147 (2007).
167. X. Chen and G. C. Flynn, Gas-phase oligosaccharide nonreducing end (GONE) sequencing and structural analysis by reversed phase HPLC/mass spectrometry with polarity switching, J. Am. Soc. Mass Spectrom., 20: 1821 (2009).
168. J. Zaia, On-line separations combined with MS for analysis of glycosaminoglycans, Mass Spectrom. Rev., 28: 254 (2009).
169. N. H. Packer, M. A. Lawson, D. R. Jardine, J. C. Sanchez and A. A. Gooley, Analyzing glycoproteins separated by two-dimensional gel electrophoresis, Electrophoresis, 19: 981 (1998).
170. N. Kawasaki, M. Ohta, S. Hyuga, O. Hashimoto and T. Hayakawa, Analysis of carbohydrate heterogeneity in a glycoprotein using liquid chromatography/mass spectrometry and liquid chromatography with tandem mass spectrometry, Anal. Biochem., 269: 297 (1999).
171. K. A. Thomsson, N. G. Karlsson and G. C. Hansson, Liquid chromatography-electrospray mass spectrometry as a tool for the analysis of sulfated oligosaccharides from mucin glycoproteins, J. Chromatogr. A, 854: 131 (1999).
172. R. P. Estrella, J. M. Whitelock, N. H. Packer and N. G. Karlsson, Graphitized carbon LC-MS characterization of the chondroitin sulfate oligosaccharides of aggrecan, Anal. Chem., 79: 3597 (2007).
173. S. Itoh, N. Kawasaki, N. Hashii, A. Harazono, Y. Matsuishi, T. Hayakawa and T. Kawanishi, N-linked oligosaccharide analysis of rat brain Thy-1 by liquid chromatography with graphitized carbon column/ion trap-Fourier transform ion cyclotron resonance mass spectrometry in positive and negative ion modes, J. Chromatogr. A, 1103: 296 (2006).
174. S. Itoh, N. Kawasaki, M. Ohta, M. Hyuga, S. Hyuga and T. Hayakawa, Simultaneous microanalysis of N-linked oligosaccharides in a glycoprotein using microbore graphitized carbon column liquid chromatography-mass spectrometry, J. Chromatogr. A, 968: 89 (2002).
175. H. Karlsson, J. M. Larsson, K. A. Thomsson, I. Hard, M. Backstrom and G. C. Hansson, High- Throughput and high-sensitivity nano-LC/MS and MS/MS for O-glycan profiling, Methods Mol. Biol., 534: 117 (2009).
176. N. G. Karlsson, B. L. Schulz and N. H. Packer, Structural determination of neutral O-linked oligosaccharide alditols by negative ion LC-electrospray-MSn, J. Am. Soc. Mass Spectrom., 15: 659 (2004).
177. N. G. Karlsson, B. L. Schulz, N. H. Packer and J. M. Whitelock, Use of graphitised carbon negative ion LC-MS to analyse enzymatically digested glycosaminoglycans, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 824: 139 (2005).
178. N. G. Karlsson, N. L. Wilson, H. J. Wirth, P. Dawes, H. Joshi and N. H. Packer, Negative ion graphitised carbon nano-liquid chromatography/mass spectrometry increases sensitivity for glycoprotein oligosaccharide analysis, Rapid Commun. Mass Spectrom., 18: 2282 (2004).
179. K. A. Thomsson, H. Karlsson and G. C. Hansson, Sequencing of sulfated oligosaccharides from mucins by liquid chromatography and electrospray ionization tandem mass spectrometry, Anal. Chem., 72: 4543 (2000).
180. N. L. Wilson, L. J. Robinson, A. Donnet, L. Bovetto, N. H. Packer and N. G. Karlsson, Glycoproteomics of milk: differences in sugar epitopes on human and bovine milk fat globule membranes, J. Proteome Res., 7: 3687 (2008).
181. M. Backstrom, K. A. Thomsson, H. Karlsson and G. C. Hansson, Sensitive liquid chromatography-electrospray mass spectrometry allows for the analysis of the O-glycosylation of immunoprecipitated proteins from cells or tissues: Application to MUC1 glycosylation in cancer, J. Proteome Res., 8: 538 (2009).
182. A. Harazono, N. Kawasaki, S. Itoh, N. Hashii, Y. Matsuishi-Nakajima, T. Kawanishi and T. Yamaguchi, Simultaneous glycosylation analysis of human serum glycoproteins by high- performance liquid chromatography/tandem mass spectrometry, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 869: 20 (2008).
183. N. Hashii, N. Kawasaki, S. Itoh, A. Harazono, Y. Matsuishi, T. Hayakawa and T. Kawanishi, Specific detection of Lewis x-carbohydrates in biological samples using liquid chromatography/multiple-stage tandem mass spectrometry, Rapid Commun. Mass Spectrom, 19: 3315 (2005).
184. N. Kawasaki, Y. Haishima, M. Ohta, S. Itoh, M. Hyuga, S. Hyuga and T. Hayakawa, Structural analysis of sulfated N-linked oligosaccharides in erythropoietin, Glycobiology, 11: 1043 (2001).
185. N. Kawasaki, S. Itoh, M. Ohta and T. Hayakawa, Microanalysis of N-linked oligosaccharides in a glycoprotein by capillary liquid chromatography/mass spectrometry and liquid chromatography/tandem mass spectrometry, Anal. Biochem., 316: 15 (2003).
186. L. R. Ruhaak, A. M. Deelder and M. Wuhrer, Oligosaccharide analysis by graphitized carbon liquid chromatography-mass spectrometry, Anal. Bioanal. Chem., 394: 163 (2009).
187. B. Barroso, M. Didraga and R. Bischoff, Analysis of proteoglycans derived sulphated disaccharides by liquid chromatography/mass spectrometry, J. Chromatogr. A, 1080: 43 (2005).
188. B. Barroso, R. Dijkstra, M. Geerts, F. Lagerwerf, P. van Veelen and A. de Ru, On-line high- performance liquid chromatography/mass spectrometric characterization of native oligosaccharides from glycoproteins, Rapid Commun. Mass Spectrom, 16: 1320 (2002).
189. C. Antonio, C. Pinheiro, M. M. Chaves, C. P. Ricardo, M. F. Ortuno and J. Thomas-Oates, Analysis of carbohydrates in Lupinus albus stems on imposition of water deficit, using porous graphitic carbon liquid chromatography-electrospray ionization mass spectrometry, J. Chromatogr. A, 1187: 111 (2008).
190. S. Robinson, E. Bergstrom, M. Seymour and J. Thomas-Oates, Screening of underivatized oligosaccharides extracted from the stems of Triticum aestivum using porous graphitized carbon liquid chromatography-mass spectrometry, Anal. Chem., 79: 2437 (2007).
191. A. Antonopoulos, P. Favetta, W. Helbert and M. Lafosse, On-line liquid chromatography- electrospray ionisation mass spectrometry for kappa-carrageenan oligosaccharides with a porous graphitic carbon column, J. Chromatogr. A, 1147: 37 (2007).
192. S. Toegel, M. Pabst, S. Q. Wu, J. Grass, M. B. Goldring, C. Chiari, A. Kolb, F. Altmann, H. Viernstein and F. M. Unger, Phenotype-related differential alpha-2, 6- or alpha-2, 3-sialylation of glycoprotein N-glycans in human chondrocytes, Osteoarthritis Cartilage (2009).
193. C. S. Chu, M. R. Ninonuevo, B. H. Clowers, P. D. Perkins, H. J. An, H. Yin, K. Killeen, S. Miyamoto, R. Grimm and C. B. Lebrilla, Profile of native N-linked glycan structures from human serum using high performance liquid chromatography on a microfluidic chip and time-of-flight mass spectrometry, Proteomics, 9: 1939 (2009).
194. M. Ninonuevo, H. An, H. Yin, K. Killeen, R. Grimm, R. Ward, B. German and C. Lebrilla, Nanoliquid chromatography-mass spectrometry of oligosaccharides employing graphitized carbon chromatography on microchip with a high-accuracy mass analyzer, Electrophoresis, 26: 3641 (2005).
195. M. R. Ninonuevo, P. D. Perkins, J. Francis, L. M. Lamotte, R. G. LoCascio, S. L. Freeman, D. A. Mills, J. B. German, R. Grimm and C. B. Lebrilla, Daily variations in oligosaccharides of human milk determined by microfluidic chips and mass spectrometry, J. Agric. Food Chem., 56: 618 (2008).
196. M. A. Bynum, H. Yin, K. Felts, Y. M. Lee, C. R. Monell and K. Killeen, Characterization of IgG N- glycans employing a microfluidic chip that integrates glycan cleavage, sample purification, LC separation, and MS detection, Anal. Chem., 81: 8818 (2009).
197. Q. Luo, T. Rejtar, S. L. Wu and B. L. Karger, Hydrophilic interaction 10 microm I.D. porous layer open tubular columns for ultratrace glycan analysis by liquid chromatography-mass spectrometry, J. Chromatogr. A, 1216: 1223 (2009).
198. M. Pabst and F. Altmann, Influence of electrosorption, solvent, temperature, and ion polarity on the performance of LC-ESI-MS using graphitic carbon for acidic oligosaccharides, Anal. Chem., 80: 7534 (2008).
199. M. S. Bereman, T. I. Williams and D. C. Muddiman, Development of a nanoLC LTQ orbitrap mass spectrometric method for profiling glycans derived from plasma from healthy, benign tumor control, and epithelial ovarian cancer patients, Anal. Chem., 81: 1130 (2009).
200. M. Pabst, J. S. Bondili, J. Stadlmann, L. Mach and F. Altmann, Mass + retention time = structure: A strategy for the analysis of N-glycans by carbon LC-ESI-MS and its application to fibrin N-glycans, Anal. Chem., 79: 5051 (2007).
201. J. Stadlmann, M. Pabst, D. Kolarich, R. Kunert and F. Altmann, Analysis of immunoglobulin glycosylation by LC-ESI-MS of glycopeptides and oligosaccharides, Proteomics, 8: 2858 (2008).
202. H. Ito, K. Yamada, K. Deguchi, H. Nakagawa and S. Nishimura, Structural assignment of disialylated biantennary N-glycan isomers derivatized with 2-aminopyridine using negative-ion multistage tandem mass spectral matching, Rapid Commun. Mass Spectrom., 21: 212 (2007).
203. A. Broberg, High-performance liquid chromatography/electrospray ionization ion-trap mass spectrometry for analysis of oligosaccharides derivatized by reductive amination and N, N-dimethylation, Carbohydr. Res., 342: 1462 (2007).
204. L. P. Brull, V. Kovacik, J. E. Thomas-Oates, W. Heerma and J. Haverkamp, Sodium-cationized oligosaccharides do not appear to undergo "internal residue loss" rearrangement processes on tandem mass spectrometry, Rapid Commun. Mass Spectrom., 12: 1520 (1998).
205. M. Wuhrer, C. A. Koeleman and A. M. Deelder, Hexose rearrangements upon fragmentation of N-glycopeptides and reductively aminated N-glycans, Anal. Chem., 81: 4422 (2009).
206. D. J. Harvey, T. S. Mattu, M. R. Wormald, L. Royle, R. A. Dwek and P. M. Rudd, "Internal residue loss": rearrangements occurring during the fragmentation of carbohydrates derivatized at the reducing terminus, Anal. Chem., 74: 734 (2002).
207. M. Wuhrer, A. R. de Boer and A. M. Deelder, Structural glycomics using hydrophilic interaction chromatography (HILIC) with mass spectrometry, Mass Spectrom. Rev., 28: 192 (2009).
208. P. J. Domann, A. C. Pardos-Pardos, D. L. Fernandes, D. I. Spencer, C. M. Radcliffe, L. Royle, R. A. Dwek and P. M. Rudd, Separation-based glycoprofiling approaches using fluorescent labels, Proteomics, 7 Suppl 1: 70 (2007).
209. M. Wuhrer, C. A. Koeleman, A. M. Deelder and C. H. Hokke, Normal-phase nanoscale liquid chromatography-mass spectrometry of underivatized oligosaccharides at low-femtomole sensitivity, Anal. Chem., 76: 833 (2004).
210. M. Wuhrer, C. A. Koeleman, C. H. Hokke and A. M. Deelder, Nano-scale liquid chromatography-mass spectrometry of 2-aminobenzamide labeled oligosaccharides at low femtomole sensitivity, Int. J. Mass Spec., 232: 51 (2004).
211. J. Zhao, W. Qiu, D. M. Simeone and D. M. Lubman, N-linked glycosylation profiling of pancreatic cancer serum using capillary liquid phase separation coupled with mass spectrometric analysis, J. Proteome Res., 6: 1126 (2007).
212. G. O. Staples, M. J. Bowman, C. E. Costello, A. M. Hitchcock, J. M. Lau, N. Leymarie, C. Miller, H. Naimy, X. Shi and J. Zaia, A chip-based amide-HILIC LC/MS platform for glycosaminoglycan glycomics profiling, Proteomics, 9: 686 (2009).
213. Y. Takegawa, H. Ito, T. Keira, K. Deguchi, H. Nakagawa and S. Nishimura, Profiling of N- And O-glycopeptides of erythropoietin by capillary zwitterionic type of hydrophilic interaction chromatography/electrospray ionization mass spectrometry, J. Sep. Sci., 31: 1585 (2008).
214. S. O. Kolset, K. Prydz and G. Pejler, Intracellular proteoglycans, Biochem. J., 379: 217 (2004).
215. N. S. Gandhi and R. L. Mancera, The Structure of glycosaminoglycans and their interactions with proteins, Chem. Biol. Drug. Des., 72: 455 (2008).
216. D. G. Seidler, J. Peter-Katalini and A. D. Zamfir, Galactosaminoglycan function and oligosaccharide structure determination, Sci. World. J., 7: 233 (2007).
217. N. Itano, Simple primary structure, complex turnover regulation and multiple roles of hyaluronan, J. Biochem., 144: 131 (2008).
218. B. P. Toole, Hyaluronan in morphogenesis, J. Intern. Med., 242: 35 (1997).
219. B. P. Toole, T. N. Wight and M. I. Tammi, Hyaluronanncell interactions in cancer and vascular disease, J. Biol. Chem., 277: 4593 (2002).
220. W. Y. Chen and G. Abatangelo, Functions of hyaluronan in wound repair, Wound Repair Regen., 7: 79 (1999).
221. A. Migliore and M. Granata, Intra-articular use of hyaluronic acid in the treatment of osteoarthritis, Clin. Interv. Aging 3: 365 (2008).
222. A. Aruffo, I. Stamenkovic, M. Melnick, C. B. Underhill and B. Seed, CD44 is the principal cell surface receptor for hyaluronate, Cell 61: 1303 (1990).
223. P. Heldin, E. Karousou, B. Bernert, H. Porsch, K. Nishitsuka and S. S. Skandalis, Importance of hyaluronan-CD44 interactions in inflammation and tumorigenesis, Connect. Tissue Res., 49: 215 (2008).
224. N. K. Karamanos, P. Vanky, A. Syrokou and A. Hjerpe, Identity of dermatan and chondroitin sequences in dermatan sulfate chains determined by using fragmentation with chondroitinases and ion-pair high-performance liquid chromatography, Anal. Biochem., 225: 220 (1995).
225. M. Kusche-Gullberg and L. Kjellen, Sulfotransferases in glycosaminoglycan biosynthesis, Curr. Opin. Struct. Biol., 13: 605 (2003).
226. K. Sugahara and S. Yamada, Structure and function of oversulfated chondroitin sulfate variants: unique sulfation patterns and neuroregulatory activities, Trends Glycosci. Glycotechnol., 12: 321 (2000).
227. K. Sugahara and T. Mikami, Chondroitin/dermatan sulfate in the central nervous system, Curr. Opin. Struct. Biol., 17: 536 (2007).
228. J. T.mar, K. Lapis, J. Dudas, A. Sebestyen, L. Kopper and I. Kovalszky, Proteoglycans and tumor progression: Janus-faced molecules with contradictory functions in cancer, Semin. Cancer Biol., 12: 173 (2002).
229. F. Li, G. B. ten Dam, S. Murugan, S. Yamada, T. Hashiguchi, S. Mizumoto, K. Oguri, M. Okayama, T. H. van Kuppevelt and K. Sugahara, Involvement of Highly Sulfated Chondroitin Sulfate in the Metastasis of the Lewis Lung Carcinoma Cells, J. Biol. Chem., 283: 34294 (2008).
230. Y. Zhang, Y. Kariya, A. H. Conrad, E. S. Tasheva and G. W. Conrad, Analysis of Keratan Sulfate Oligosaccharides by Electrospray Ionization Tandem Mass Spectrometry, Anal. Chem., 77: 902 (2005).
231. B. Mulloy and M. J. Forster, Conformation and Dynamics of Heparin and Heparan Sulfate, Glycobiology, 10: 1147 (2000).
232. R. Lawrence, S. K. Olson, R. E. Steele, L. Wang, R. Warrior, R. D. Cummings and J. D. Esko, Evolutionary Differences in Glycosaminoglycan Fine Structure Detected by Quantitative Glycan Reductive Isotope Labeling, J. Biol. Chem., 283: 33674 (2008).
233. U. Lindahl, Heparan sulfate-protein interactions n A concept for drug design?, Thromb. Haemost., 98: 109 (2007).
234. M. J. Miller, C. E. Costello, A. Malmstrom and J. A. Zaia, A tandem mass spectrometric approach to determination of chondroitin/dermatan sulfate oligosaccharide glycoforms, Glycobiology, 16: 502 (2006).
235. A. Ziegler and J. A. Zaia, Separation of heparin oligosaccharides by size-exclusion chromatography, J. Chromatogr. B. Analytical Technologies in the Biomedical and Life Sciences, 837: 76 (2006).
236. A. M. Hitchcock, C. E. Costello and J. A. Zaia, Glycoform quantification of chondroitin/dermatan sulfate using an LC/MS/MS platform, Biochemistry, 45: 2350 (2006).
237. A. K. Korir, J. F. Limtiaco, S. M. Gutierrez and C. K. Larive, Ultraperformance ion-pair liquid chromatography coupled to electrospray time-of-flight mass spectrometry for compositional profiling and quantification of heparin and heparan sulfate, Anal. Chem., 80: 1297 (2008).
238. A. D. Zamfir, D. G. Seidler, H. Kresse and J. Peter-Katalinic, Structural characterization of chondroitin/dermatan sulfate oligosaccharides from bovine aorta by capillary electrophoresis and electrospray ionization quadrupole time-of-flight tandem mass spectrometry, Rapid Commun. Mass Spectrom., 16: 2015 (2002).
239. A. D. Zamfir, D. G. Seidler, H. Kresse and J. Peter-Katalinic, Structural investigation of chondroitin/dermatan sulfate oligosaccharides from human skin fibroblast decorin, Glycobiology, 13: 733 (2003).
240. D. J. Mahoney, R. T. Aplin, A. Calabro, V. C. Hascall and A. J. Day, Novel methods for the preparation and characterization of hyaluronan oligosaccharides of defined length, Glycobiology, 11: 1025 (2001).
241. J. Zaia, B. Liu, R. Boynton and F. Barry, Structural analysis of cartilage proteoglycans and glycoproteins using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, Anal. Biochem., 277: 94 (2000).
242. N. Keiser, G. Venkataraman, Z. Shriver and R. Sasisekharan, Direct isolation and sequencing of specific protein-binding glycosaminoglycans, Nature Med., 7: 123 (2001).
243. T. N. Mitropoulou, F. Lamari, A. Syrokou, A. Hjerpe and N. Karamanos, Identification of oligomeric domains within dermatan sulfate chains using differential enzymic treatments, derivatization with 2-aminoacridone and capillary electrophoresis, Electrophoresis 22: 2458 (2001).
244. J. Zaia, J. E. McClellan and C. E. Costello, Tandem mass spectrometric determination of the 4S/6S sulfation sequence in chondroitin sulfate oligosaccharides, Anal. Chem., 73: 6030 (2001).
245. A. Tawada, T. Masa, Y. Oonuki, A. Watanabe, Y. Matsuzaki and A. Asari, Large-scale preparation, purification, and characterization of hyaluronan oligosaccharides from 4-mers to 52- mers, Glycobiology, 12: 421 (2002).
246. S. Yamada, Y. Okada, M. Ueno, S. Iwata, S. S. Deepa, S. Nishimura, M. Fujita, I. van Die, Y. Hirabayashi and K. Sugahara, Determination of the glycosaminoglycan-protein linkage region oligosaccharide structures of proteoglycans from Drosophila melanogaster and Caenorhabditis elegans, J. Biol. Chem., 277: 31877 (2002).
247. A. V. Kuhn, H. H. Ruttinger, R. H. Neubert and K. Raith, Identification of hyaluronic acid oligosaccharides by direct coupling of capillary electrophoresis with electrospray ion trap mass spectrometry, Rapid Commun. Mass Spectrom., 17: 576 (2003).
248. S. Duteil, P. Gareil, S. Girault, A. Mallet, C. Feve and L. Siret, Identification of heparin oligosaccharides by direct coupling of capillary electrophoresis/ionspray-mass spectrometry, Rapid Commun. Mass Spectrom., 13: 1889 (1999).
249. V. Ruiz-Calero, E. Moyano, L. Puignou and M. T. Galceran, Pressure-assisted capillary electrophoresis-electrospray ion trap mass spectrometry for the analysis of heparin depolymerised disaccharides, J . Chromatogr. A, 914: 277 (2001).
250. S. Fermas, F. Gonnet, A. Varenne, P. Gareil and R. Daniel, Frontal analysis capillary electrophoresis hyphenated to electrospray ionization mass spectrometry for the characterization of the antithrombin/heparin pentasaccharide complex, Anal. Chem., 79: 4987 (2007).
251. L. Svennerholm, Gangliosides and synaptic transmission, Adv. Exp. Med. Biol., 125: 11 (1980).
252. UPAC-IUB Joint Commission on Biochemical Nomenclature, Nomenclature of glycolipids, Eur. J. Biochem.,, 257: 293 (1998).
253. R. K. Yu, Y. Nakatani and M. Yanagisawa, The role of glycosphingolipid metabolism in the developing brain, J. Lipid Res., 50: 440 (2009).
254. J. S. Ryu, K. Ko, J. W. Lee, S. B. Park, S. J. Byun, E. J. Jeong, K. Ko and Y. K. Choo, Gangliosides are involved in neural differentiation of human dental pulp-derived stem cells, Biochem. Biophys. Res. Commun., 387: 266 (2009).
255. P. McJarrow, N. Schnell, J. Jumpsen and T. Clandinin, Nutr. Rev., 67: 451 (2009).
256. M. Taniguchi, T. Tashiro, N. Dashtsoodol, N. Hongo and H. Watarai, The specialized iNKT cell system recognizes glycolipid antigens and bridges the innate and acquired immune systems with potential applications for cancer therapy, Int. Immunol, 22: 1 (2010).
257. G. Zhang, H. Zhang, Q. Wang, P. Lal, A. M. Carroll, M. de la Llera-Moya, X. Xu and M. I. Greene, Suppression of human prostate tumor growth by a unique prostate-specific monoclonal antibody F77 targeting a glycolipid marker, Proc. Natl. Acad. Sc. U.S.A., 107: 732 (2010).
258. S. Hakomori, Tumor-associated carbohydrate antigens defining tumor malignancy: basis for development of anti-cancer vaccines, Adv. Exp. Med. Biol., 491: 369 (2001).
259. S. Hakomori and K. Handa, Glycosphingolipid-dependent cross-talk between glycosynapses interfacing tumor cells with their host cells: essential basis to define tumor malignancy, FEBS Lett., 531: 88 (2002).
260. S. B. Levery, Glycosphingolipid structural analysis and glycosphingolipidomics, Methods Enzymol., 405: 300 (2005).
261. U. Distler, M. Hulsewig, J. Souady, K. Dreisewerd, J. Haier, N. Senninger, A. W. Friedrich, H. Karch, F. Hillenkamp, S. Berkenkamp, J. Peter-Katalini. and J. Muthing, Matching IR-MALDI-o-TOF mass spectrometry with the TLC overlay binding assay and its clinical application for tracing tumor-associated glycosphingolipids in hepatocellular and pancreatic cancer, Anal. Chem., 80: 1835 (2008).
262. M. C. Sullards, J. C. Allegood, S. Kelly, E. Wang, C. A. Haynes, H. Park, Y. Chen and A. H. Merrill Jr., Structure-specific, quantitative methods for analysis of sphingolipids by liquid chromatography-tandem mass spectrometry: "inside-out" sphingolipidomics, Methods Enzymol., 432: 95 (2007).
263. T. Ariga, M. P. McDonald and R. K. Yu, Role of ganglioside metabolism in the pathogenesis of Alzheimeris disease, J. Lipid Res., 49: 1157 (2008).
264. W. R. Jung, H. G. Kim and K. L. Kim, Ganglioside GQ1b improves spatial learning and memory of rats as measured by the Y-maze and the Morris water maze tests, Neurosci. Lett., 439: 220 (2008).
265. Y. Fujimoto, S. Izumoto, T. Suzuki, M. Kinoshita, N. Kagawa, K. Wada, N. Hashimoto, M. Maruno, Y. Nakatsuji and T. Yoshimine, Ganglioside GM3 inhibits proliferation and invasion of glioma, J. Neurooncol., 71: 99 (2005).
266. Z. Vukeli, S. Kalanj-Bognar, M. Froesch, L. Bindila, B. Radi., M. Allen, J. Peter-Katalini. and A. D. Zamfir, Human gliosarcoma-associated ganglioside composition is complex and distinctive as evidenced by high-performance mass spectrometric determination and structural characterization, Glycobiology, 17: 504 (2007).
267. A. D. Zamfir, Vukelic and J. Peter-Katalini., A capillary electrophoresis and off-line capillary electrophoresis/electrospray ionization-quadrupole time of flight-tandem mass spectrometry approach for ganglioside analysis, Electrophoresis, 23: 2894 (2002).
268. J. Li, A. Martin, A. D. Cox, E. R. Moxon, J. C. Richards and P. Thibault, in Methods in Enzymology (Mass Spectrometry: Modified Proteins and Glycoconjugates), Vol. 405 Elsevier, Amsterdam, 2005, p. 369.
269. C. W. Reid, J. Stupak, M. M. Chen, B. Imperiali, J. Li and C. M. Szymanski, Affinity-Capture Tandem Mass Spectrometric Characterization of Polyprenyl-Linked Oligosaccharides: Tool to Study Protein N-Glycosylation Pathways, Anal. Chem., 80: 5468 (2008).
270. D. D. Ju, C. C. Lai and G. R. Her, Analysis of gangliosides by capillary zone electrophoresis and capillary zone electrophoresis-electrospray mass spectrometry, J. Chromatogr. A, 779: 195 (1997).
271. Y. R. Chen, M. C. Tseng and G. R. Her, Design and performance of a low-flow capillary electrophoresis-electrospray-mass spectrometry interface using an emitter with dual beveled edge, Electrophoresis, 26: 1376 (2005).
272. P. Liuni, T. Rob and D. J. Wilson, A microfluidic reactor for rapid, low-pressure proteolysis with on-chip electrospray ionization, Rapid Commun. Mass Spectrom., 24: 315 (2010).
273. J. Lee, S. A. Soper and K. K. Murray, Microfluidic chips for mass spectrometry-based proteomics, J. Mass Spectrom., 44: 579 (2009).
274. A. Serb, C. Schiopu, C. Flangea, .. Vukeli., E. Sisu, L. Zagrean and A. D. Zamfir, High-throughput analysis of gangliosides in defined regions of fetal brain by fully automated chipbased nanoelectrospray ionization multistage mass spectrometry, Eur. J. Mass Spectrom., 15: 541 (2009).
275. R. Almeida, C. Mosoarca, M. Chirita, V. Udrescu, N. Dinca, Vukeli, M. Allen and A. D. Zamfir, Coupling of fully automated chip-based electrospray ionization to high-capacity ion trap mass spectrometer for ganglioside analysis, Anal. Biochem., 378: 52 (2008).
276. A. D. Zamfir, L. Bindila, N. Lion, M. Allen, H. H. Girault and J. Peter-Katalinic, Chip electrospray mass spectrometry for carbohydrate analysis, Electrophoresis, 26: 3650 (2005).
277. A. D. Zamfir, Z. Vukeli., L. Bindila, J. Peter-Katalini., R. Almeida, A. Sterling and M. Allen, Fully- Automated chip-based nanoelectrospray tandem mass spectrometry of gangliosides from human cerebellum, J. Am. Soc. Mass Spectrom.: 1649 (2004).
278. A. Serb, C. Schiopu, C. Flangea, E. Sisu and A. D. Zamfir, Top-down glycolipidomics: fragmentation analysis of ganglioside oligosaccharide core and ceramide moiety by chip- nanoelectrospray collision-induced dissociation MS2-MS6, J. Mass Spectrom., 44: 1434 (2009).
279. C. Schiopu, A. Serb, F. Capitan, C. Flangea, E. Sisu, Z. Vukelic, S. Kalanj-Bognar, M. Przybylski and A. D. Zamfir, Determination of ganglioside composition and structure in human brain hemangioma by chip-based nanoelectrospray ionization tandem mass spectrometry, Anal. Bioanal. Chem., 395: 2465 (2009).