Electron transfer dissociation of milk oligosaccharides

Journal of the American Society for Mass Spectrometry

Volumn 22, Issue 6, 2011, Pages 997-1013

  Han, Liang ^a,b   Costello, Catherine E ^a,b  

^a BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Boston University   (United States)

Author keywords

Collision induced dissociation; Electron transfer dissociation; Fragmentation; Milk oligosaccharides; O 18 stable isotope label; Permethylated glycans

Indexed keywords

COLLISION-INDUCED DISSOCIATION; ELECTRON TRANSFER DISSOCIATION; FRAGMENTATION; GLYCANS; MILK OLIGOSACCHARIDES; O-18 STABLE ISOTOPE LABEL;

CARBOHYDRATES; CLARIFICATION; ELECTRON TRANSITIONS; IONS; ISOTOPES; OLIGOSACCHARIDES; STRUCTURAL ANALYSIS;

DISSOCIATION;

LACTOSE; OLIGOSACCHARIDE;

ARTICLE; COLLISIONALLY ACTIVATED DISSOCIATION; DISSOCIATION; DNA FRAGMENTATION; ELECTRON TRANSFER DISSOCIATION; ELECTRON TRANSPORT; MASS SPECTROMETRY; MILK; PROTEIN CLEAVAGE; PROTEIN STRUCTURE; STRUCTURE ANALYSIS;

ANIMALS; CARBOHYDRATE CONFORMATION; CATIONS; ELECTRONS; METALS; METHYLATION; MILK; OLIGOSACCHARIDES; TANDEM MASS SPECTROMETRY;

EID: 79955855048     PISSN: 10440305     EISSN: 18791123     Source Type: Journal    
DOI: 10.1007/s13361-011-0117-9     Document Type: Article

References (45)

1. K Ohtsubo JD Marth 2006 Glycosylation in Cellular Mechanisms of Health and Disease Cell 126 855 867 10.1016/j.cell.2006.08.019 1:CAS:528: DC%2BD28XpvVKitbo%3D (Pubitemid 44310784)
2. Varki, A.; Cummings, R.D.; Esko, J.D.; Freeze, H.H.; Hart, G.W.; Marth, J.: Essentials of Glycobiology. Cold Spring Harbor Laboratory Press, Cold Spring Harbor (1999)
3. Mutenda, K.E.; Matthiesen, R.: Analysis of Carbohydrates by Mass Spectrometry. In: Matthiesen, R. (ed.) Mass spectrometry data analysis in proteomics, p. 289. Humana Press, Totowa (2006)
4. Xie, B.; Costello, C.E.: Carbohydrate Structure Determination by Mass spectrometry. In: Cowman, M.K.; Garg, H.G.; Hales, C.A. (eds.) Carbohydrate Chemistry, Biology, and Medical Applications, p. 29. Elsevier, Ltd, New York (2008)
5. n Anal. Chem. 77 6250 6262 10.1021/ac050724z 1:CAS:528:DC%2BD2MXpsFOrsLo%3D (Pubitemid 41436960)
6. VN Reinhold BB Reinhold CE Costello 1995 Carbohydrate Molecular-Weight Profiling, sSequence, Linkage, and Branching Data-ES-MS and CID Anal. Chem. 67 1772 1784 10.1021/ac00107a005 1:CAS:528:DyaK2MXlsFeksLs%3D
7. J Lemoine B Fournet D Despeyroux KR Jennings R Rosenberg E de Hoffmann 1993 Collision-Induced Dissociation of Alkali-Metal Cationized and Permethylated Oligosaccharides-Influence of the Collision Energy and of the Collision Gas for the Assignment of Linkage Position J. Am. Soc. Mass Spectrom. 4 197 203 10.1016/1044-0305(93)85081-8 1:CAS:528:DyaK3sXmsFShu7c%3D
8. DJ Harvey RH Bateman MR Green 1997 High-Energy Collision-Induced Fragmentation of Complex Oligosaccharides Ionized by Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry J. Mass Spectrom. 32 167 187 10.1002/(SICI)1096-9888(199702)32:2<167::AID-JMS472>3.0.CO;2-Q 1:CAS:528:DyaK2sXhsVarurg%3D (Pubitemid 27087384)
9. JT Adamson K Hakansson 2007 Electron Capture Dissociation of Oligosaccharides Ionized with Alkali, Alkaline Earth, and Transition Metals Anal. Chem. 79 2901 2910 10.1021/ac0621423 1:CAS:528:DC%2BD2sXitF2htL0%3D (Pubitemid 46595645)
10. C Zhao B Xie SY Chan CE Costello PB O'Connor 2008 Collisionally Activated Dissociation and Electron Capture Dissociation Provide Complementary Structural Information for Branched Permethylated Oligosaccharides J. Am. Soc. Mass Spectrom. 19 138 150 10.1016/j.jasms.2007.10.022 1:CAS:528: DC%2BD1cXosFKltQ%3D%3D
11. JJ Wolff LL Chi RJ Linhardt IJ Amster 2007 Distinguishing Glucuronic from Iduronic Acid in Glycosaminoglycan Tetrasaccharides by Using Electron Detachment Dissociation Anal. Chem. 79 2015 2022 10.1021/ac061636x 1:CAS:528:DC%2BD2sXot1Wrtg%3D%3D (Pubitemid 46355233)
12. JJ Wolff IJ Amster LL Chi RJ Linhardt 2007 Electron Detachment Dissociation of Glycosaminoglycan Tetrasaccharides J. Am. Soc. Mass Spectrom. 18 234 244 10.1016/j.jasms.2006.09.020 1:CAS:528:DC%2BD2sXht1Wgs70%3D (Pubitemid 46150099)
13. JT Adamson K Hakansson 2007 Electron Detachment Dissociation of Neutral and Sialylated Oligosaccharides J. Am. Soc. Mass Spectrom. 18 2162 2172 10.1016/j.jasms.2007.09.007 1:CAS:528:DC%2BD2sXhtlynsb%2FP (Pubitemid 350161325)
14. JEP Syka JJ Coon MJ Schroeder J Shabanowitz DF Hunt 2004 Peptide and Protein Sequence Analysis by Electron Transfer Dissociation Mass Spectrometry Proc. Natl. Acad. Sci. U.S.A. 101 9528 9533 10.1073/pnas.0402700101 1:CAS:528:DC%2BD2cXlvVahs70%3D (Pubitemid 38869270)
15. J Wiesner T Premsler A Sickmann 2008 Application of Electron Transfer Dissociation (ETD) for the Analysis of Post-Translational Modifications Proteomics 8 4466 4483 10.1002/pmic.200800329 1:CAS:528:DC%2BD1cXhsVCjtrrL
16. H Molina DM Horn N Tang S Mathivanan A Pandey 2007 Global Proteomic Profiling of Phosphopeptides Using Electron Transfer Dissociation Tandem Mass sSpectrometry Proc. Natl. Acad. Sci. U.S.A. 104 2199 2204 10.1073/pnas. 0611217104 1:CAS:528:DC%2BD2sXisVWrsLk%3D (Pubitemid 46391375)
17. JM Hogan SJ Pitteri PA Chrisman SA McLuckey 2005 Complementary Structural Information from a Tryptic N-Linked Glycopeptide Via Electron Transfer Ion/Ion Reactions and Collision-Induced Dissociation J. Proteome Res. 4 628 632 10.1021/pr049770q 1:CAS:528:DC%2BD2MXitVClurc%3D (Pubitemid 40548173)
18. RE March 2000 Quadrupole Ion Trap Mass Spectrometry: A View at the Turn of the Century Int. J. Mass Spectrom. 200 285 312 10.1016/S1387-3806(00)00345-6 1:CAS:528:DC%2BD3MXosl2rsQ%3D%3D (Pubitemid 32036679)
19. n Data Anal. Chem. 77 6271 6279 10.1021/ac050726j 1:CAS:528:DC%2BD2MXpsFOrsLg%3D (Pubitemid 41436962)
20. N Viseux E de Hoffmann B Domon 1998 Structural Assignment of Permethylated Oligosaccharide Subunits Using Sequential Tandem Mass Spectrometry Anal. Chem. 70 4951 4959 10.1021/ac980443+ 1:CAS:528:DyaK1cXmvVKjt7g%3D (Pubitemid 28553164)
21. N Viseux E de Hoffmann B Domon 1997 Structural Analysis of Permethylated Oligosaccharides by Electrospray Tandem Mass Spectrometry Anal. Chem. 69 3193 3198 10.1021/ac961285u 1:CAS:528:DyaK2sXkslKhsrY%3D (Pubitemid 27357542)
22. DM Sheeley VN Reinhold 1998 Structural Characterization of Carbohydrate Sequence, Linkage, and Branching in a Quadrupole Ion Trap Mass Spectrometer: Neutral Oligosaccharides and N-Linked Glycans Anal. Chem. 70 3053 3059 10.1021/ac9713058 1:CAS:528:DyaK1cXjvVWktL4%3D (Pubitemid 128484659)
23. DJ Ashline AJ Lapadula YH Liu M Lin M Grace B Pramanik VN Reinhold 2007 Carbohydrate Structural Isomers Analyzed by Sequential Mass Spectrometry Anal. Chem. 79 3830 3842 10.1021/ac062383a 1:CAS:528:DC%2BD2sXjs1Gisrg%3D (Pubitemid 46799080)
24. JA Carroll D Willard CB Lebrilla 1995 Energetics of Cross-Ring Cleavages and Their Relevance to the Linkage Determination of Oligosaccharides Anal. Chim. Acta 307 43 447 10.1016/0003-2670(94)00514-M
25. DJ Harvey 2001 Ionization and Collision-Induced Fragmentation of N-Linked and Related Carbohydrates Using Divalent Canons J. Am. Soc. Mass Spectrom. 12 926 937 10.1016/S1044-0305(01)00268-9 1:CAS:528:DC%2BD3MXltlKrtro%3D
26. GE Hofmeister Z Zhou JA Leary 1991 Linkage Position Determination in Lithium-Cationized Disaccharides-Tandem Mass-Spectrometry and Semiempirical Calculations J. Am. Chem. Soc. 113 5964 5970 10.1021/ja00016a007 1:CAS:528:DyaK3MXkvFaksbo%3D
27. DJ Harvey 2000 Collision-Induced Fragmentation of Underivatized N-Linked Carbohydrates Ionized by Electrospray J. Mass Spectrom. 35 1178 1190 10.1002/1096-9888(200010)35:10<1178::AID-JMS46>3.0.CO;2-F 1:CAS:528:DC%2BD3cXotFWlurY%3D
28. 2+-Coordinated Branched Trisaccharide Isomers-an Electrospray-Ionization and Tandem Mass-Spectrometry Study Anal. Chem. 65 2805 2811 10.1021/ac00068a017 1:CAS:528:DyaK3sXmt1Khurs%3D
29. MT Cancilla SG Penn JA Carroll CB Lebrilla 1996 Coordination of Alkali Metals to Oligosaccharides Dictates Fragmentation Behavior in Matrix-Assisted Laser Desorption/Ionization Fourier Transform Mass Spectrometry J. Am. Chem. Soc. 118 6736 6745 10.1021/ja9603766 1:CAS:528:DyaK28XjvVSisL0%3D (Pubitemid 26248170)
30. J Zaia 2004 Mass Spectrometry of Oligosaccharides Mass Spectrom. Rev. 23 161 227 10.1002/mas.10073 1:CAS:528:DC%2BD2cXktVOmu7g%3D
31. J Zaia 2008 Mass Spectrometry and the Emerging Field of Glycomics Chem. Biol. 15 881 892 10.1016/j.chembiol.2008.07.016 1:CAS:528:DC%2BD1cXhtFCnsr3M
32. J Lemoine F Chirat B Domon 1996 Structural Analysis of Derivatized Oligosaccharides Using Post-Source Decay Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry J. Mass Spectrom. 31 908 912 10.1002/(SICI)1096-9888(199608)31:8<908::AID-JMS376>3.0.CO;2-D 1:CAS:528:DyaK28XkvFSgtLc%3D (Pubitemid 26258970)
33. Y Mechref P Kang MV Novotny 2006 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 1389 10.1002/rcm.2445 1:CAS:528:DC%2BD28XktVCntLw%3D
34. EM Sible SP Brimmer JA Leary 1997 Interaction of First Row Transition Metals with α 1-3, α 1-6 Mannotriose and Conserved Trimannosyl Core Oligosaccharides: A Comparative Electrospray Ionization Study of Doubly and Singly Charged Complexes J. Am. Soc. Mass Spectrom. 8 32 42 10.1016/S1044- 0305(97)82229-5 1:CAS:528:DyaK2sXitVWjtA%3D%3D (Pubitemid 27020059)
35. Sinnott, M.L.: Carbohydrate Chemistry and Biochemistry, 1st edn. The Royal Society of Chemistry, Cambridge (2007)
36. BA Garcia DY Gin 2000 Dehydrative Glycosylation with Activated Diphenyl Sulfonium Reagents. Scope, Mode of C(1)-Hemiacetal Activation, and Detection of Reactive Glycosyl Intermediates J. Am. Chem. Soc. 122 4269 4279 10.1021/ja993595a 1:CAS:528:DC%2BD3cXisFGiu7w%3D (Pubitemid 30317080)
37. CE Costello JM Contado-Miller JF Cipollo 2007 A Glycomics Platform for the Analysis of Permethylated Oligosaccharide Alditols J. Am. Soc. Mass Spectrom. 18 1799 1812 10.1016/j.jasms.2007.07.016 1:CAS:528:DC%2BD2sXhtVOmu7zP (Pubitemid 47419346)
38. I Ciucanu F Kerek 1984 A Simple and Rapid Method for the Permethylation of Carbohydrates Carbohydr. Res. 131 209 217 10.1016/0008-6215(84)85242-8 1:CAS:528:DyaL2cXlvFahu7Y%3D
39. I Ciucanu CE Costello 2003 Elimination of Oxidative Degradation During the per-O-Methylation of Carbohydrates J. Am. Chem. Soc. 125 16213 16219 10.1021/ja035660t 1:CAS:528:DC%2BD3sXpsFOktbc%3D (Pubitemid 38020645)
40. DL Swaney GC McAlister M Wirtala JC Schwartz JEP Syka JJ Coon 2007 Supplemental Activation Method for High-Efficiency Electron-Transfer Dissociation of Doubly Protonated Peptide Precursors Anal. Chem. 79 477 485 10.1021/ac061457f 1:CAS:528:DC%2BD28Xht12itbvK (Pubitemid 46110632)
41. B Domon CE Costello 1988 A Systematic Nomenclature for Carbohydrate Fragmentations in FAB-MSMS Spectra of Glycoconjugates Glycoconj. J. 5 397 409 10.1007/BF01049915 1:CAS:528:DyaL1MXitVyks7g%3D (Pubitemid 19031141)
42. DF Hunt GC Stafford FW Crow JW Russell 1976 Pulsed Positive-Negative-Ion Chemical Ionization Mass Spectrometry Anal. Chem. 48 2098 2105 10.1021/ac50008a014 1:CAS:528:DyaE28XlvVKgsLs%3D
43. HP Gunawardena M He PA Chrisman SJ Pitteri JM Hogan BDM Hodges SA McLuckey 2005 Electron Transfer Versus Proton Transfer in Gas-Phase Ion/Ion Reactions of Polyprotonated Peptides J. Am. Chem. Soc. 127 12627 12639 10.1021/ja0526057 1:CAS:528:DC%2BD2MXotVSlt7Y%3D (Pubitemid 41292180)
44. B Gyurcsik L Nagy 2000 Carbohydrates as Ligands: Coordination Equilibria and Structure of the Metal Complexes Coord. Chem. Rev. 203 81 149 10.1016/S0010-8545(99)00183-6 1:CAS:528:DC%2BD3cXktFegur8%3D
45. YJ Zheng RL Ornstein JA Leary 1997 A Density Functional Theory Investigation of Metal Ion Binding Sites in Monosaccharides Theochem-J. Mol. Struct. 389 233 240 10.1016/S0166-1280(96)04707-0 1:CAS:528:DyaK2sXisVCrsbs%3D (Pubitemid 127380968)