Structural characterization of carbohydrates by fourier transform tandem mass spectrometry

Current Proteomics

Volumn 8, Issue 4, 2011, Pages 297-308

  Zhou, Wen ^a   Håkansson, Kristina ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Electron capture dissociation (ECD); Electron detachment dissociation (EDD); Glycosylation; Infrared multiphoton dissociation (IRMPD); Oligosaccharides; Tandem mass spectrometry

Indexed keywords

CARBOHYDRATE; GLYCAN DERIVATIVE; GLYCOSAMINOGLYCAN;

ACCURACY; ANALYTIC METHOD; BIOSYNTHESIS; CARBOHYDRATE ANALYSIS; COLLISIONALLY ACTIVATED DISSOCIATION; DERIVATIZATION; ELECTRON CAPTURE DISSOCIATION; ELECTRON DETACHMENT DISSOCIATION; ELECTRON INDUCED DISSOCIATION; FOURIER TRANSFORM MASS SPECTROMETRY; INFRARED MULTIPHOTON DISSOCIATION; IONIZATION; PRIORITY JOURNAL; PROTEIN PROCESSING; REVIEW; SENSITIVITY ANALYSIS;

EID: 82155171405     PISSN: 15701646     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016411798220826     Document Type: Review

References (146)

1. Varki, A. Biological roles of oligosaccharides - All of the theories are correct. Glycobiol., 1993, 3, 97-130.
2. Rudd, P. M.; Elliott, T.; Cresswell, P.; Wilson, I. A. and Dwek, R. A. Glycosylation and the immune system. Science, 2001, 291, 2370-2376.
3. Bertozzi, C. R. and Kiessling, L. L. Chemical glycobiology. Science, 2001, 291, 2357-2364.
4. Krishnamoorthy, L. and Mahal, L. K. Glycomic analysis: an array of technologies. ACS Chem. Biol., 2009, 4, 715-732.
5. Dwek, R. A. Glycobiology: Toward understanding the function of sugars. Chem. Rev., 1996, 96, 683-720.
6. Raman, R.; Raguram, S.; Venkataraman, G.; Paulson, J. C. and Sasisekharan, R. Glycomics: an integrated systems approach to structure-function relationships of glycans. Nat. Methods, 2005, 2, 817-824.
7. Mechref, Y. and Novotny, M. V. Structural investigations of glycoconjugates at high sensitivity. Chem. Rev., 2002, 102, 321-369.
8. Zaia, J. Mass spectrometry and the emerging field of glycomics. Chem. Biol., 2008, 15, 881-892.
9. Harvey, D. J. Proteomic analysis of glycosylation: structural determination of N- and O-linked glycans by mass spectrometry. Expert Rev. Proteomics, 2005, 2, 87-101.
10. Domon, B. and Costello, C. E. A systematic nomenclature for carbohydrate fragmentations in FAB-MS MS spectra of glycoconjugates Glycoconj. J., 1988, 5, 397-409.
11. Ashline, D.; Singh, S.; Hanneman, A. and Reinhold, V. Congruent strategies for carbohydrate sequencing. 1. Mining structural details by MSn. Anal. Chem., 2005, 77, 6250-6262.
12. Ashline, D. J.; Lapadula, A. J.; Liu, Y. H.; Lin, M.; Grace, M.; Pramanik, B. and Reinhold, V. N. Carbohydrate structural isomers analyzed by sequential mass spectrometry. Anal. Chem., 2007, 79, 3830-3842.
13. Prien, J. M.; Ashline, D. J.; Lapadula, A. J.; Zhang, H. and Reinhold, V. N. The high mannose glycans from bovine ribonuclease B isomer characterization by ion trap MS. J. Am. Soc. Mass. Spectrom., 2009, 20, 539-556.
14. Huzarska, M.; Ugalde, I.; Kaplan, D. A.; Hartmer, R.; Easterling, M. L. and Polfer, N. C. Negative electron transfer dissociation of deprotonated phosphopeptide anions: choice of radical cation reagent and competition between electron and proton transfer. Anal. Chem., 2010, 82, 2873-2878.
15. Wolff, J. J.; Leach, F. E.; Laremore, T. N.; Kaplan, D. A.; Easterling, M. L.; Linhardt, R. J. and Amster, I. J. Negative electron transfer dissociation of glycosaminoglycans. Anal. Chem., 2010, 82, 3460-3466.
16. Devakumar, A.; Mechref, Y.; Kang, P.; Novotny, M. V. and Reilly, J. P. Laser-induced photofragmentation of neutral and acidic glycans inside an ion-trap mass spectrometer. Rapid Commun. Mass Spectrom., 2007, 21, 1452-1460.
17. Devakumar, A.; Mechref, Y.; Kang, P.; Novotny, M. V. and Reilly, J. P. Identification of isomeric N-glycan structures by mass spectrometry with 157 nm laser-induced photofragmentationJ. Am. Soc. Mass. Spectrom., 2008, 19, 1027-1040.
18. Wilson, J. J. and Brodbelt, J. S. Ultraviolet photodissociation at 355 nm of fluorescently labeled oligosaccharides. Anal. Chem., 2008, 80, 5186-5196.
19. Harvey, D. J. Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. Mass Spectrom. Rev., 1999, 18, 349-450.
20. Harvey, D. J. Identification of protein-bound carbohydrates by mass spectrometry. Proteomics, 2001, 1, 311-328.
21. Zaia, J. Mass spectrometry of oligosaccharides. Mass Spectrom. Rev., 2004, 23, 161-227.
22. Park, Y. M. and Lebrilla, C. B. Application of Fourier transform ion cyclotron resonance mass spectrometry to oligosaccharides. Mass Spectrom. Rev., 2005, 24, 232-264.
23. Huberty, M. C.; Vath, J. E.; Yu, W. and Martin, S. A. Site-specific carbohydrate identification in recombinant proteins using MALDI- TOF MS. Anal. Chem., 1993, 65, 2791-2800.
24. Lancaster, K. S.; An, H. J.; Li, B. S. and Lebrilla, C. B. Interrogation of N-linked oligosaccharides using infrared multiphoton dissociation in FT-ICR mass spectrometry. Anal. Chem., 2006, 78, 4990-4997.
25. Karas, M.; Bahr, U. and Dulcks, T. Nano-electrospray ionization mass spectrometry: addressing analytical problems beyond routine. Fresenius J. Anal. Chem., 2000, 366, 669-676.
26. Kebarle, P. and Verkerk, U. H. Electrospray: from ions in solution to ions in the gas phase, what we know now. Mass Spectrom. Rev., 2009, 28, 898-917.
27. Pabst, M.; Kolarich, D.; Poltl, G.; Dalik, T.; Lubec, G.; Hofinger, A. and Altmann, F. Comparison of fluorescent labels for oligosaccharides and introduction of a new postlabeling purification method. Anal. Biochem., 2009, 384, 263-273.
28. Yoshino, K.; Takao, T.; Murata, H. and Shimonishi, Y. Use of the derivatizing agent 4-aminobenzoic acid 2-(diethylamino)ethyl ester for high-sensitivity detection of oligosaccharides by electrospray-ionization mass-spectrometry. Anal. Chem., 1995, 67, 4028-4031.
29. Bahr, U.; Pfenninger, A.; Karas, M. and Stahl, B. High sensitivity analysisof neutralunderivatizedoligosaccharidesby nanoelectrospray mass spectrometry. Anal. Chem., 1997, 69, 4530-4535.
30. Bereman, M. S.; Williams, T. I. and Muddiman, D. C. 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., 2009, 81, 1130-1136.
31. Luo, Q. Z.; Rejtar, T.; Wu, S. L. and Karger, B. L. Hydrophilic interaction 10 mu m ID porous layer open tubular columns for ultratrace glycan analysis by liquid chromatography-mass spectrometry. J. Chromatogr. A., 2009, 1216, 1223-1231.
32. Thomsson, K. A.; Backstrom, M.; Larsson, J. M. H.; Hansson, G. C. and Karlsson, H. Enhanced detection of sialylated and sulfated glycans with negative ion mode nanoliquid chromatography/mass spectrometry at high pH. Anal. Chem., 2010, 82, 1470-1477.
33. Wohlgemuth, J.; Karas, M.; Jiang, W.; Hendriks, R. and Andrecht, S. Enhanced glyco-profiling by specific glycopeptide enrichment and complementary monolithic nano-LC (ZIC-HILIC/RP18e)/ESI- MS analysis. J. Sep. Sci., 2010, 33, 880-890.
34. Tretter, V.; Altmann, F. and Marz, L. Peptide-N4-(N-acetyl-beta-glycosaminyl)asparagine amidase-F cannot release glycans with fucose attached alpha-1-3 to the asparagine-linked N- acetylglucosamine residue Eur. J. Biochem., 1991, 199, 647-652.
35. Tarentin. Al; Plummer, T. H. and Maley, F. Release of intact oligosaccharides from specfic glycoproteins by endo-beta-N-acetylglucosaminidase H J. Biol. Chem., 1974, 249, 818-824.
36. Adolf, G. R.; Kalsner, I.; Ahorn, H.; Maurerfogy, I. and Cantell, K. Natural human interferon-alpha-2 is O-glycosylated. Biochem. J., 1991, 276, 511-518.
37. Patel, T.; Bruce, J.; Merry, A.; Bigge, C.; Wormald, M.; Jaques, A. and Parekh, R. Use of hydrazine to release in intact and unreduced form both N-linked and O-linked oligosaccharides from glycoproteins. Biochemistry (Mosc). 1993, 32, 679-693.
38. Harvey, D. J. Electrospray mass spectrometry and collision-induced fragmentation of 2-aminobenzamide-labelled neutral N- linked glycans. Analyst, 2000, 125, 609-617.
39. Wheeler, S. F. and Harvey, D. J. 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.
40. Maniatis, S.; Zhou, H. and Reinhold, V. Rapid de-O-glycosylation concomitant with peptide labeling using microwave radiation and an alkyl amine base. Anal. Chem., 2010, 82, 2421-2425.
41. Anumula, K. R. Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Anal. Biochem., 2006, 350, 1-23.
42. Goetz, J. A.; Novotny, M. V. and Mechref, Y. Enzymatic/chemical release of O-glycans allowing MS analysis at high sensitivity. Anal. Chem., 2009, 81, 9546-9552.
43. Ruhaak, L. R.; Zauner, G.; Huhn, C.; Bruggink, C.; Deelder, A. M. and Wuhrer, M. Glycan labeling strategies and their use in identification and quantification. Anal. Bioanal. Chem., 2010, 397, 3457-3481.
44. Mechref, Y.; Kang, P. and Novotny, M. V. 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., 2006, 20, 1381-1389.
45. Sheeley, D. M. and Reinhold, V. N. Structural characterization of carbohydrate sequence, linkage, and branching in a quadrupole ion trap mass spectrometer: Neutral oligosaccharides and N-linked glycans. Anal. Chem., 1998, 70, 3053-3059.
46. Ciucanu, I. and Kerek, F. A simple and rapid method for the permethylation of carbohydrates. Carbohydr. Res., 1984, 131, 209-217.
47. Kang, P.; Mechref, Y.; Klouckova, I. and Novotny, M. V. Solid-phase permethylation of glycans for mass spectrometric analysis. Rapid Commun. Mass Spectrom., 2005, 19, 3421-3428.
48. Kang, P.; Mechref, Y. and Novotny, M. V. High-throughput solid-phase permethylation of glycans prior to mass spectrometry. Rapid Commun. Mass Spectrom., 2008, 22, 721-734.
49. Lei, M.; Mechref, Y. and Novotny, M. V. Structural analysis of sulfated glycans by sequential double-permethylation using methyl iodide and deuteromethyl iodide. J. Am. Soc. Mass. Spectrom., 2009, 20, 1660-1671.
50. Wuhrer, M. and Deelder, A. M. Negative-mode MALDI-TOF/TOF-MS of oligosaccharides labeled with 2-aminobenzamide. Anal. Chem., 2005, 77, 6954-6959.
51. Harvey, D. J. Collision-induced fragmentation of negative ions from N-linked glycans derivatized with 2-aminobenzoic acid. J. Mass Spectrom., 2005, 40, 642-653.
52. Wuhrer, M.; Koeleman, C. A. M. and Deelder, A. M. Hexose rearrangements upon fragmentation of N-glycopeptides and reductively aminated N-glycans. Anal. Chem., 2009, 81, 4422-4432.
53. Lamari, F. N.; Kuhn, R. and Karamanos, N. K. Derivatization of carbohydrates for chromatographic, electrophoretic and mass spectrometric structure analysis. J. Chromatogr. B., 2003, 793, 15-36.
54. Lattova, E.; Snovida, S.; Perreault, H. and Krokhin, O. Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry. J. Am. Soc. Mass. Spectrom., 2005, 16, 683-696.
55. Hofmeister, G. E.; Zhou, Z. and Leary, J. A. Linkage position determination in lithium-cationized disaccharides - tandem mass-sepctrometry and semiempirical calculations J. Am. Chem. Soc., 1991, 113, 5964-5970.
56. Sible, E. M.; Brimmer, S. P. and Leary, J. A. Interaction of first row transition metals with alpha 1-3, alpha 1-6 mannotriose and conserved trimannosyl core oligosaccharides: A comparative electrospray ionization study of doubly and singly charged complexes. J. Am. Soc. Mass. Spectrom., 1997, 8, 32-42.
57. Konig, S. and Leary, J. A. Evidence for linkage position determination in cobalt coordinated pentasaccharides using ion trap mass spectrometry. J. Am. Soc. Mass. Spectrom., 1998, 9, 1125-1134.
58. Cancilla, M. T.; Penn, S. G.; Carroll, J. A. and Lebrilla, C. B. Coordination of alkali metals to oligosaccharides dictates fragmentation behavior in matrix assisted laser desorption ionization Fourier transform mass spectrometry. J. Am. Chem. Soc., 1996, 118, 6736-6745.
59. Xie, Y. M. and Lebrilla, C. B. Infrared multiphoton dissociation of alkali metal-coordinated oligosaccharides. Anal. Chem., 2003, 75, 1590-1598.
60. Adamson, J. T. and Hakansson, K. Electron capture dissociation of oligosaccharides ionized with alkali, alkaline earth, and transition metals. Anal. Chem., 2007, 79, 2901-2910.
61. Harvey, D. J. Ionization and collision-induced fragmentation of N-linked and related carbohydrates using divalent canons. J. Am. Soc. Mass. Spectrom., 2001, 12, 926-937.
62. Liu, H. C. and Hakansson, K. Divalent metal ion-peptide interactions probed by electron capture dissociation of trications. J. Am. Soc. Mass. Spectrom., 2006, 17, 1731-1741.
63. Liu, H. and Hakansson, K. Analysis of sulfated oligosaccharides with combination of divalent metal complexation and electron capture dissociation. Int. J. Mass Spectrom., 2011.
64. Harvey, D. J.; Mattu, T. S.; Wormald, M. R.; Royle, L.; Dwek, R. A. and Rudd, P. M. Internal residue loss: Rearrangements occurring during the fragmentation of carbohydrates derivatized at the reducing terminus. Anal. Chem., 2002, 74, 734-740.
65. Franz, A. H. and Lebrilla, C. B. Evidence for long-range glycosyl transfer reactions in the gas phase. J. Am. Soc. Mass. Spectrom., 2002, 13, 325-337.
66. Ernst, B.; Muller, D. R. and Richter, W. J. False sugar sequence ions in electrospray tandem mass spectrometry of underivatized sialyl-Lewis-type oligosaccharides. Int. J. Mass Spectrom. Ion Processes, 1997, 160, 283-290.
67. Wuhrer, M.; Koeleman, C. A. M.; Hokke, C. H. and Deelder, A. M. Mass spectrometry of proton adducts of fucosylated N-glycans: fucose transfer between antennae gives rise to misleading fragments. Rapid Commun. Mass Spectrom., 2006, 20, 1747-1754.
68. Harvey, D. J. Fragmentation of negative ions from carbohydrates: Part 1. Use of nitrate and other anionic adducts for the production of negative ion electrospray spectra from N-linked carbohydrates. J. Am. Soc. Mass. Spectrom., 2005, 16, 622-630.
69. Zhu, J. H. and Cole, R. B. Ranking of gas-phase acidities and chloride affinities of monosaccharides and linkage specificity in collision-induced decompositions of negative ion electrospray-generated chloride adducts of oligosaccharides. J. Am. Soc. Mass. Spectrom., 2001, 12, 1193-1204.
70. Cai, Y.; Jiang, Y. J. and Cole, R. B. Anionic adducts of oligosaccharides by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal. Chem., 2003, 75, 1638-1644.
71. Jiang, Y. J. and Cole, R. B. Oligosaccharide analysis using anion attachment in negative mode electrospray mass spectrometry. J. Am. Soc. Mass. Spectrom., 2005, 16, 60-70.
72. Marshall, A. G.; Hendrickson, C. L. and Jackson, G. S. Fourier transform ion cyclotron resonance mass spectrometry: A primer. Mass Spectrom. Rev., 1998, 17, 1-35.
73. Perry, R. H.; Cooks, R. G. and Noll, R. J. Orbitrap mass spectrometry: instrumentation, ion motion and applications Mass Spectrom. Rev., 2008, 27, 661-699.
74. Hu, Q. Z.; Noll, R. J.; Li, H. Y.; Makarov, A.; Hardman, M. and Cooks, R. G. The Orbitrap: a new mass spectrometer. J. Mass Spectrom., 2005, 40, 430-443.
75. Yates, J. R.; Ruse, C. I. and Nakorchevsky, A. Proteomics by mass spectrometry: approaches, advances, and applications. Annu. Rev. Biomed. Eng., 2009, 11, 49-79.
76. Marshall, A. G. and Hendrickson, C. L. High-resolution mass spectrometers. Annu. Rev. Anal. Chem., 2008, 1, 579-599.
77. Scigelova, M. and Makarov, A. Orbitrap mass analyzer - Overview and applications in proteomics. Proteomics, 2006, 16-21.
78. Makarov, A.; Denisov, E.; Lange, O. and Horning, S. Dynamic range of mass accuracy in LTQ Orbitrap hybrid mass spectrometer. J. Am. Soc. Mass. Spectrom., 2006, 17, 977-982.
79. Packer, N. H. and Karlsson, N. G. There are no facts, only interpretations. J. Proteome Res., 2006, 5, 1291-1292.
80. Sleno, L.; Volmer, D. A. and Marshall, A. G. Assigning product ions from complex MS/MS spectra: The importance of mass uncertainty and resolving power. J. Am. Soc. Mass. Spectrom., 2005, 16, 183-198.
81. Zubarev, R. A.; Kelleher, N. L. and McLafferty, F. W. Electron capture dissociation of multiply charged protein cations. A nonergodic process. J. Am. Chem. Soc., 1998, 120, 3265-3266.
82. Budnik, B. A.; Haselmann, K. F. and Zubarev, R. A. Electron detachment dissociation of peptide di-anions: an electron-hole recombination phenomenon. Chem. Phys. Lett., 2001, 342, 299-302.
83. Syka, J. E. P.; Coon, J. J.; Schroeder, M. J.; Shabanowitz, J. and Hunt, D. F. Peptide and protein sequence analysis by electron transfer dissociation mass spectrometry. Proc. Natl. Acad. Sci. USA, 2004, 101, 9528-9533.
84. Bushey, J. M.; Baba, T. and Glish, G. L. Simultaneous collision induced dissociation of the charge reduced parent ion during electron capture dissociation. Anal. Chem., 2009, 81, 6156-6164.
85. Silivra, O. A.; Kjeldsen, F.; Ivonin, I. A. and Zubarev, R. A. Electron capture dissociation of polypeptides in a three- dimensional quadrupole ion trap: Implementation and first results. J. Am. Soc. Mass. Spectrom., 2005, 16, 22-27.
86. Baba, T.; Hashimoto, Y.; Hasegawa, H.; Hirabayashi, A. and Waki, I. Electron capture dissociation in a radio frequency ion trap. Anal. Chem., 2004, 76, 4263-4266.
87. Ding, L. and Brancia, F. L. Electron capture dissociation in a digital ion trap mass spectrometer. Anal. Chem., 2006, 78, 1995-2000.
88. McCullough, B. J.; Entwistle, A.; Konishi, I.; Buffey, S.; Hasnain, S. S.; Brancia, F. L.; Grossmann, J. G. and Gaskell, S. J. Digital ion trap mass spectrometer for probing the structure of biological macromolecules by gas phase X-ray scattering. Anal. Chem., 2009, 81, 3392-3397.
89. Wiesner, J.; Premsler, T. and Sickmann, A. Application of electron transfer dissociation (ETD) for the analysis of posttranslational modifications. Proteomics, 2008, 8, 4466-4483.
90. McAlister, G. C.; Berggren, W. T.; Griep-Raming, J.; Horning, S.; Makarov, A.; Phanstiel, D.; Stafford, G.; Swaney, D. L.; Syka, J. E. P.; Zabrouskov, V. and Coon, J. J. A proteomics grade electron transfer dissociation-enabled hybrid linear ion trap-orbitrap mass spectrometer. J. Proteome Res., 2008, 7, 3127-3136.
91. McAlister, G. C.; Phanstiel, D.; Good, D. M.; Berggren, W. T. and Coon, J. J. Implementation of electron-transfer dissociation on a hybrid linear ion trap-orbitrap mass spectrometer. Anal. Chem., 2007, 79, 3525-3534.
92. Carroll, J. A.; Ngoka, L.; Beggs, C. G. and Lebrilla, C. B. Liquid secondary-ion mass-spectrometry Fourier-transformmass-spectrometry of oligosaccharide anions. Anal. Chem., 1993, 65, 1582-1587.
93. Harvey, D. J. Fragmentation of negative ions from carbohydrates: Part 2. Fragmentation of high-mannose N-linked glycans. J. Am. Soc. Mass. Spectrom., 2005, 16, 631-646.
94. Harvey, D. J. Fragmentation of negative ions from carbohydrates: Part 3. Fragmentation of hybrid and complex N-linked glycans. J. Am. Soc. Mass. Spectrom., 2005, 16, 647-659.
95. Seymour, J. L.; Costello, C. E. and Zaia, J. The influence of sialylation on glycan negative ion dissociation and energetics. J. Am. Soc. Mass. Spectrom., 2006, 17, 844-854.
96. Harvey, D. J.; Bateman, R. H. and Green, M. R. High-energy collision-induced fragmentation of complex oligosaccharides ionized by matrix-assisted laser desorption/ionization mass spectrometry. J. Mass Spectrom., 1997, 32, 167-187.
97. Mechref, Y.; Novotny, M. V. and Krishnan, C. Structural characterization of oligosaccharides using MALDI-TOF/TOF tandem mass spectrometry. Anal. Chem., 2003, 75, 4895-4903.
98. Yu, S. Y.; Wu, S. W. and Khoo, K. H. Distinctive characteristics of MALDI-Q/TOF and TOF/TOF tandem mass spectrometry for sequencing of permethylated complex type N-glycans. Glycoconj. J., 2006, 23, 355-369.
99. Maslen, S. L.; Goubet, F.; Adam, A.; Dupree, P. and Stephens, E. Structure elucidation of arabinoxylan isomers by normal phase HPLC-MALDI-TOF/TOF-MS/MS. Carbohydr. Res., 2007, 342, 724-735.
100. Hakansson, K.; Cooper, H. J.; Hudgins, R. R. and Nilsson, C. L. High resolution tandem mass spectrometry for structural biochemistry. Curr. Org. Chem., 2003, 7, 1503-1525.
101. Gauthier, J. W.; Trautman, T. R. and Jacobson, D. B. Sustained off-resonance irradiation for collision-activated dissociation involving Fourier-transform mass spectrometry -collision-activated dissociation technique that emulates infrared multiphoton dissociation Anal. Chim. Acta, 1991, 246, 211-225.
102. Solouki, T.; Reinhold, B. B.; Costello, C. E.; O'Malley, M.; Guan, S. H. and Marshall, A. G. Electrospray ionization and matrix-assisted laser desorption/ionization Fourier transform ion cyclotron resonance mass spectrometry of permethylated oligosaccharides. Anal. Chem., 1998, 70, 857-864.
103. Aguilan, J. T.; Dayrit, F. M.; Zhang, J. H.; Ninonuevo, M. R. and Lebrilla, C. B. Structural analysis of alpha-carrageenan sulfated oligosaccharides by positive mode nano-ESI-FTICR-MS and MS/MS by SORI-CID. J. Am. Soc. Mass. Spectrom., 2006, 17, 96-103.
104. Leavell, M. D.; Kruppa, G. H. and Leary, J. A. Determination of phosphate position in hexose monosaccharides using an FTICR mass spectrometer: ion/molecule reactions, labeling studies, and dissociation mechanisms. Int. J. Mass Spectrom., 2003, 222, 135-153.
105. Cancilla, M. T.; Wang, A. W.; Voss, L. R. and Lebrilla, C. B. Fragmentation reactions in the mass spectrometry analysis of neutral oligosaccharides. Anal. Chem., 1999, 71, 3206-3218.
106. Pitteri, S. J. and McLuckey, S. A. Recent developments in the ion/ion chemistry of high-mass multiply charged ions. Mass Spectrom. Rev., 2005, 24, 931-958.
107. Huang, T. Y. and McLuckey, S. A. Annu. Rev. Anal. Chem., 2010, 3, 365-385.
108. Olsen, J. V.; Macek, B.; Lange, O.; Makarov, A.; Horning, S. and Mann, M. Higher-energy C-trap dissociation for peptide modification analysis. Nat. Methods, 2007, 4, 709-712.
109. Zhang, Y.; Ficarro, S. B.; Li, S. J. and Marto, J. A. Optimized Orbitrap HCD for quantitative analysis of phosphopeptides. J. Am. Soc. Mass. Spectrom., 2009, 20, 1425-1434.
110. Wu, J. A.; Warren, P.; Shakey, Q.; Sousa, E.; Hill, A.; Ryan, T. E. and He, T. Integrating titania enrichment, iTRAQ labeling, and Orbitrap CID-HCD for global identification and quantitative analysis of phosphopeptides. Proteomics, 2010, 10, 2224-2234.
111. Brodbelt, J. S. and Wilson, J. J. Infrared multiphoton dissociation in quadrupole ion traps. Mass Spectrom. Rev., 2009, 28, 390-424.
112. Vala, M.; Szczepanski, J.; Oomens, J. and Steill, J. D. H-2 Ejection from Polycyclic Aromatic Hydrocarbons: Infrared Multiphoton Dissociation Study of Protonated 1,2-Dihydronaphthalene. J. Am. Chem. Soc., 2009, 131, 5784-5791.
113. Stefan, S. E. and Eyler, J. R. Differentiation of methyl-glucopyranoside anomers by infrared multiple photon dissociation with a tunable CO2 laser. Anal. Chem., 2009, 81, 1224-1227.
114. Vala, M.; Szczepanski, J.; Dunbar, R.; Oomens, J. and Steill, J. D. Infrared multiphoton dissociation spectrum of isolated protonated 1-azapyrene. Chem. Phys. Lett., 2009, 473, 43-48.
115. Polfer, N. C.; Valle, J. J.; Moore, D. T.; Oomens, J.; Eyler, J. R. and Bendiak, B. Differentiation of isomers by wavelength-tunable infrared multiple-photon dissociation-mass spectrometry: Application to glucose-containing disaccharides. Anal. Chem., 2006, 78, 670-679.
116. Hakansson, K. and Klassen, J. S. In Electrospray and MALDI Mass Spectrometry: Fundamentals, Instrumentation, Practicalities, and Biological Applications; 2nd ed.; Cole, R. B., Ed.; John Wiley & Sons, Inc., Hoboken, New Jersey: 2010.
117. Zhang, J. H.; Schubothe, K.; Li, B. S.; Russell, S. and Lebrilla, C. B. Infrared multiphoton dissociation of O-linked mucin-type oligosaccharides. Anal. Chem., 2005, 77, 208-214.
118. An, H. J.; Miyamoto, S.; Lancaster, K. S.; Kirmiz, C.; Li, B. S.; Lam, K. S.; Leiserowitz, G. S. and Lebrilla, C. B. Profiling of glycans in serum for the discovery of potential biomarkers for ovarian cancer. J. Proteome Res., 2006, 5, 1626-1635.
119. Zubarev, R. A.; Horn, D. M.; Fridriksson, E. K.; Kelleher, N. L.; Kruger, N. A.; Lewis, M. A.; Carpenter, B. K. and McLafferty, F. W. Electron capture dissociation for structural characterization of multiply charged protein cations. Anal. Chem., 2000, 72, 563-573.
120. McLafferty, F. W.; Horn, D. M.; Breuker, K.; Ge, Y.; Lewis, M. A.; Cerda, B.; Zubarev, R. A. and Carpenter, B. K. Electron capture dissociation of gaseous multiply charged ions by Fourier-transform ion cyclotron resonance. J. Am. Soc. Mass. Spectrom., 2001, 12, 245-249.
121. Zubarev, R. A. Reactions of polypeptide ions with electrons in the gas phase. Mass Spectrom. Rev., 2003, 22, 57-77.
122. Cooper, H. J.; Hakansson, K. and Marshall, A. G. The role of electron capture dissociation in biomolecular analysis. Mass Spectrom. Rev., 2005, 24, 201-222.
123. Hakansson, K.; Cooper, H. J.; Emmett, M. R.; Costello, C. E.; Marshall, A. G. and Nilsson, C. L. Electron capture dissociation and infrared multiphoton dissociation MS/MS of an N-glycosylated tryptic peptide to yield complementary sequence information. Anal. Chem., 2001, 73, 4530-4536.
124. Hakansson, K.; Chalmers, M. J.; Quinn, J. P.; McFarland, M. A.; Hendrickson, C. L. and Marshall, A. G. Combined electron capture and infrared multiphoton dissociation for multistage MS/MS in a Fourier transform ion cyclotron resonance mass spectrometer. Anal. Chem., 2003, 75, 3256-3262.
125. Mirgorodskaya, E.; Roepstorff, P. and Zubarev, R. A. Localization of O-glycosylation sites in peptides by electron capture dissociation in a fourier transform mass spectrometer. Anal. Chem., 1999, 71, 4431-4436.
126. Stensballe, A.; Jensen, O. N.; Olsen, J. V.; Haselmann, K. F. and Zubarev, R. A. Electron capture dissociation of singly and multiply phosphorylated peptides. Rapid Commun. Mass Spectrom., 2000, 14, 1793-1800.
127. Shi, S. D. H.; Hemling, M. E.; Carr, S. A.; Horn, D. M.; Lindh, I. and McLafferty, F. W. Phosphopeptide/phosphoprotein mapping by electron capture dissociation mass spectrometry. Anal. Chem., 2001, 73, 19-22.
128. Budnik, B. A.; Haselmann, K. F.; Elkin, Y. N.; Gorbach, V. I. and Zubarev, R. A. Applications of electron-ion dissociation reactions for analysis of polycationic chitooligosaccharides in Fourier transform mass spectrometry. Anal. Chem., 2003, 75, 5994-6001.
129. Zhou, W. and Hakansson, K. Electron capture dissociation of metal-adducted N-linked oligosaccharides released from bovine thyroid stimulating hormone. In Proc. 56th ASMS Conference on Mass Spectrometry and Allied Topics. Denver, CO, 2008.
130. Zhao, C.; Xie, B.; Chan, S. Y.; Costello, C. E. and O'Connor, P. B. Collisionally activated dissociation and electron capture dissociation provide complementary structural information for branched permethylated oligosaccharides. J. Am. Soc. Mass. Spectrom., 2008, 19, 138-150.
131. Kalli, A. and Hakansson, K. Preferential cleavage of S-S and C-S bonds in electron detachment dissociation and infrared multiphoton dissociation of disulfide-linked peptide anions. Int. J. Mass Spectrom., 2007, 263, 71-81.
132. Haselmann, K. F.; Budnik, B. A.; Kjeldsen, F.; Nielsen, M. L.; Olsen, J. V. and Zubarev, R. A. Electronic excitation gives informative fragmentation of polypeptide cations and anions. Eur. J. Mass Spectrom., 2002, 8, 117-121.
133. Yang, J.; Mo, J. J.; Adamson, J. T. and Hakansson, K. Characterization of oligodeoxynucleotides by electron detachment dissociation Fourier transform ion cyclotron resonance mass spectrometry. Anal. Chem., 2005, 77, 1876-1882.
134. Yang, J. and Hakansson, K. Fragmentation of oligoribonucleotides from gas-phase ion-electron reactions. J. Am. Soc. Mass. Spectrom., 2006, 17, 1369-1375.
135. McFarland, M. A.; Marshall, A. G.; Hendrickson, C. L.; Nilsson, C. L.; Fredman, P. and Mansson, J. E. Structural characterization of the GM1 ganglioside by infrared multiphoton dissociation/electron capture dissociation, and electron detachment dissociation electrospray ionization FT-ICR MS/MS. J. Am. Soc. Mass. Spectrom., 2005, 16, 752-762.
136. Adamson, J. T. and Hakansson, K. Electron detachment dissociation of neutral and sialylated oligosaccharides. J. Am. Soc. Mass. Spectrom., 2007, 18, 2162-2172.
137. Wolff, J. J.; Amster, I. J.; Chi, L. L. and Linhardt, R. J. Electron detachment dissociation of glycosaminoglycan tetrasaccharides. J. Am. Soc. Mass. Spectrom., 2007, 18, 234-244.
138. Wolff, J. J.; Chi, L. L.; Linhardt, R. J. and Amster, I. J. Distinguishing glucuronic from iduronic acid in glycosaminoglycan tetrasaccharides by using electron detachment dissociation. Anal. Chem., 2007, 79, 2015-2022.
139. Wolff, J. J.; Laremore, T. N.; Busch, A. M.; Linhardt, R. J. and Amster, I. J. Electron detachment dissociation of dermatan sulfate oligosaccharides. J. Am. Soc. Mass. Spectrom., 2008, 19, 294-304.
140. Wolff, J. J.; Laremore, T. N.; Busch, A. M.; Linhardt, R. J. and Amster, I. J. Influence of charge state and sodium cationization on the electron detachment dissociation and infrared multiphoton dissociation of glycosaminoglycan oligosaccharides. J. Am. Soc. Mass. Spectrom., 2008, 19, 790-798.
141. Wolff, J. J.; Laremore, T. N.; Leach, F. E.; Linhardt, R. J. and Amster, I. J. Electron capture dissociation, electron detachment dissociation and infrared multiphoton dissociation of sucrose octasulfate. Eur. J. Mass Spectrom., 2009, 15, 275-281.
142. Chi, L. L.; Wolff, J. J.; Laremore, T. N.; Restaino, O. F.; Xie, J.; Schiraldi, C.; Toida, T.; Amster, I. J. and Linhardt, R. J. Structural analysis of bikunin glycosaminoglycan. J. Am. Chem. Soc., 2008, 130, 2617-2625.
143. Wolff, J. J.; Laremore, T. N.; Aslam, H.; Linhardt, R. J. and Amster, I. J. Electron-induced dissociation of glycosaminoglycan tetrasaccharides. J. Am. Soc. Mass. Spectrom., 2008, 19, 1449-1458.
144. Zhou, W. and Håkansson, K. Ion-electron reactions of sialylated N- linked glycans released from glycoproteins. In Proc. 57th ASMS Conference on Mass Spectrometry and Allied Topics. Philadelphia, PA, 2009.
145. Yoo, H. J.; Liu, H. C. and Hakansson, K. Infrared multiphoton dissociation and electron-induced dissociation as alternative MS/MS strategies for metabolite identification. Anal. Chem., 2007, 79, 7858-7866.
146. th ASMS Conference on Mass Spectrometry and Allied Topics. Salt Lake City, UT, 2010.