Fragmentation of negative ions from N-linked carbohydrates: Part 6. Glycans containing one N-acetylglucosamine in the core

Rapid Communications in Mass Spectrometry

Volumn 28, Issue 18, 2014, Pages 2008-2018

  Harvey, David J ^a,b   Edgeworth, Matthew ^b   Krishna, Benjamin A ^c   Bonomelli, Camille ^a   Allman, Sarah A ^d   Crispin, Max ^a   Scrivens, James H ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d OPEN UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; ION SOURCES; ISOMERS; POLYSACCHARIDES; POSITIVE IONS;

COLLISION INDUCED DISSOCIATION; COLLISION-INDUCED DISSOCIATION SPECTRA; GLYCANS; ION COLLISIONS; ION MOBILITY; N-ACETYLGLUCOSAMINE; N-GLYCAN; N-LINKED CARBOHYDRATES; POSITIVE ION SPECTRA; STRUCTURAL INFORMATION;

NEGATIVE IONS;

ANION; MANNOSE; N ACETYLGLUCOSAMINE;

CHEMISTRY; CONFORMATION; ELECTROSPRAY MASS SPECTROMETRY; PROCEDURES;

ACETYLGLUCOSAMINE; ANIONS; CARBOHYDRATE CONFORMATION; MANNOSE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84905457591     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6980     Document Type: Article

References (42)

1. T. Patel, J. Bruce, A. Merry, C. Bigge, M. Wormald, A. Jaques, R. Parekh,. Use of hydrazine to release in intact and unreduced form both N- and O-linked oligosaccharides from glycoproteins. Biochemistry 1993, 32, 679.
2. B. Küster, S. F. Wheeler, A. P. Hunter, R. A. Dwek, D. J. Harvey,. Sequencing of N-linked oligosaccharides directly from protein gels: In-gel deglycosylation followed by matrix-assisted laser desorption/ionization mass spectrometry and normal-phase high performance liquid chromatography. Anal. Biochem. 1997, 250, 82.
3. A. L. Tarentino, C. M. Gõmez, T. H. Plummer Jr,. Deglycosylation of asparagine-linked glycans by peptide:N-glycosidase F. Biochemistry 1985, 24, 4665.
4. N. Takahashi,. Demonstration of a new amidase acting on glycopeptides. Biochem. Biophys. Res. Commun. 1977, 76, 1194.
5. T. H. Plummer Jr, J. H. Elder, S. Alexander, A. W. Phelan, A. L. Tarentino,. Demonstration of peptide: N-glycosidase F activity in endo-beta-N-acetylglucosaminidase F preparations. J. Biol. Chem. 1984, 259, 10700.
6. J. E. Nettleship, R. Aplin, A. R. Aricescu, E. J. Evans, S. J. Davis, M. Crispin, R. J. Owens,. Analysis of variable N-glycosylation site occupancy in glycoproteins by liquid chromatography electrospray ionization mass spectrometry. Anal. Biochem. 2007, 361, 149.
7. A. L. Tarentino, F. Maley,. Purification and properties of an endo-β-N-acetylglucosaminidase from Streptomyces griseus. J. Biol. Chem. 1973, 249, 811.
8. E. Miyoshi, M. Nakano,. Fucosylated haptoglobin is a novel marker for pancreatic cancer: Detailed analyses of oligosaccharide structures. Proteomics 2008, 8, 3257.
9. R. Saldova, H. Piccard, M. Pérez-Garay, D. J. Harvey, W. B. Struwe, M. C. Galligan, N. Berghmans, S. F. Madden, R. Peracaula, G. Opdenakker, P. M. Rudd,. Increase in sialylation and branching in the mouse serum N-glycome correlates with inflammation and ovarian tumour progression. PLoS One 2013, 8, e71159.
10. J. J. Goodfellow, K. Baruah, K. Yamamoto, C. Bonomelli, B. Krishna, D. J. Harvey, M. Crispin, C. N. Scanlan, B. G. Davis,. An endoglycosidase with alternative glycan specificity allows broadened glycoprotein remodelling. J. Am. Chem. Soc. 2012, 134, 8030.
11. S. Prime, J. Dearnley, A. M. Ventom, R. B. Parekh, C. J. Edge,. Oligosaccharide sequencing based on exo- and endoglycosidase digestion and liquid chromatographic analysis of the products. J. Chromatogr. A 1996, 720, 263.
12. S. B. Prime, N. F. Shipston, T. H. Merry,. Enzymatic sequence analysis of glycoprotein glycans. BioMethods 1997, 9, 235.
13. C. G. Hellerqvist,. Linkage analysis using Lindberg method. Methods Enzymol. 1990, 193, 554.
14. N. P. Price,. Permethylation linkage analysis techniques for residual carbohydrates. Appl. Biochem. Biotechnol. 2008, 148, 271.
15. V. N. Reinhold, B. B. Reinhold, C. E. Costello,. Carbohydrate molecular weight profiling, sequence, linkage and branching data: ES-MS and CID. Anal. Chem. 1995, 67, 1772.
16. D. J. Harvey,. Fragmentation of negative ions from carbohydrates: Part 2. Fragmentation of high-mannose N-linked glycans. J. Am. Soc. Mass Spectrom. 2005, 16, 631.
17. D. J. Harvey,. 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.
18. D. J. Harvey,. Fragmentation of negative ions from carbohydrates: Part 3. Fragmentation of hybrid and complex N-linked glycans. J. Am. Soc. Mass Spectrom. 2005, 16, 647.
19. D. J. Harvey, L. Royle, C. M. Radcliffe, P. M. Rudd, R. A. Dwek,. Structural and quantitative analysis of N-linked glycans by MALDI and negative ion nanospray mass spectrometry. Anal. Biochem. 2008, 376, 44.
20. O. Levy-Ontman, S. Arad, D. J. Harvey, T. B. Parsons, A. Fairbanks, Y. Tekoah,. Unique N-glycan moieties of the 66-kDa cell wall glycoprotein from the red microalga Porphyridium sp. J. Biol. Chem. 2011, 286, 21340.
21. S. F. Wheeler, D. J. Harvey,. Negative ion mass spectrometry of sialylated carbohydrates: Discrimination of N-acetylneuraminic acid linkages by matrix-assisted laser desorption/ionization-time-of-flight and electrospray-time-of-flight mass spectrometry. Anal. Chem. 2000, 72, 5027.
22. S. F. Wheeler, P. Domann, D. J. Harvey,. Derivatization of sialic acids for stabilization in matrix-assisted laser desorption/ionization mass spectrometry and concomitant differentiation of α(2-3) and α(2-6) isomers. Rapid Commun. Mass Spectrom. 2009, 23, 303.
23. 1H-NMR spectroscopy. J. Biol. Chem. 1988, 263, 18253.
24. 1H-NMR characterization of a hen ovalbumin tyrosinamide N-linked oligosaccharide library. Arch. Biochem. Biophys. 1995, 318, 465.
25. D. J. Harvey, D. R. Wing, B. Küster, I. B. H. Wilson,. Composition of N-linked carbohydrates from ovalbumin and co-purified glycoproteins. J. Am. Soc. Mass Spectrom. 2000, 11, 564.
26. (R) membrane as a new sample pretreatment for matrix-assisted laser desorption-ionization mass spectrometry. Rapid Commun. Mass Spectrom. 1995, 9, 1031.
27. K. Giles, S. D. Pringle, K. R. Worthington, D. Little, J. L. Wildgoose, R. H. Bateman,. Applications of a travelling wave-based radio-frequency-only stacked ring ion guide. Rapid Commun. Mass Spectrom. 2004, 18, 2401.
28. B. Domon, C. E. Costello,. A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J. 1988, 5, 397.
29. H. Li, K. Giles, B. Bendiak, K. Kaplan, W. F. Siems, H. H. Hill Jr,. Resolving structural isomers of monosaccharide methyl glycosides using drift tube and traveling wave ion mobility mass spectrometry. Anal. Chem. 2012, 84, 3231.
30. J. P. Williams, M. Grabenauer, C. J. Carpenter, R. J. Holland, M. R. Wormald, K. Giles, D. J. Harvey, R. H. Bateman, J. H. Scrivens, M. T. Bowers,. Characterization of simple isomeric oligosaccharides and the rapid separation of glycan mixtures by ion mobility mass spectrometry. Int. J. Mass Spectrom. 2010, 298, 119.
31. Y. Yamaguchi, W. Nishima, S. Re, Y. Sugita,. Confident identification of isomeric N-glycan structures by combined ion mobility mass spectrometry and hydrophilic interaction liquid chromatography. Rapid Commun. Mass Spectrom. 2012, 26, 2877.
32. B. H. Clowers, P. Dwivedi, W. E. Steiner, H. H. J. Hill, B. Bendiak,. Separation of sodiated isobaric disaccharides and trisaccharides using electrospray ionization-atmospheric pressure ion mobility-time of flight mass spectrometry. J. Am. Soc. Mass Spectrom. 2005, 16, 660.
33. P. Dwivedi, B. Bendiak, B. H. Clowers, H. H. J. Hill,. Rapid resolution of carbohydrate isomers by electrospray ionization ambient pressure ion mobility spectrometry-time-of-flight mass spectrometry (ESI-APIMS-TOFMS). J. Am. Soc. Mass Spectrom. 2007, 18, 1163.
34. M. D. Plasencia, D. Isailovic, S. I. Merenbloom, Y. Mechref, D. E. Clemmer,. Resolving and assigning N-linked glycan structural isomers from ovalbumin by IMS-MS. J. Am. Soc. Mass Spectrom. 2008, 19, 1706.
35. L. S. Fenn, J. A. McLean,. Structural resolution of carbohydrate positional and structural isomers based on gas-phase ion mobility-mass spectrometry. Phys. Chem. Chem. Phys. 2011, 13, 2196.
36. P. M. Lalli, Y. E. Corilo, M. Fasciotti, M. F. Riccio, G. F. de Sa, R. J. Daroda, G. H. M. F. Souza, M. McCullagh, M. D. Bartberger, M. N. Eberlin, I. D. G. Campuzano,. Baseline resolution of isomers by traveling wave ion mobility mass spectrometry: investigating the effects of polarizable drift gases and ionic charge distribution. J. Mass Spectrom. 2013, 48, 989.
37. Y. Huang, E. D. Dodds,. Ion mobility studies of carbohydrates as group I adducts: Isomer specific collisional cross section dependence on metal ion radius. Anal. Chem. 2013, 85, 9728.
38. H. Li, B. Bendiak, K. Kaplan, E. Davis, W. F. Siems, H. J. H. Hill,. Evaluation of ion mobility-mass spectrometry for determining the isomeric heterogeneity of oligosaccharide-alditols derived from bovine submaxillary mucin. Int. J. Mass Spectrom. 2013, 352, 9.
39. S. D. Pringle, K. Giles, J. L. Wildgoose, J. P. Williams, S. E. Slade, K. Thalassinos, R. H. Bateman, M. T. Bowers, J. H. Scrivens,. An investigation of the mobility separation of some peptide and protein ions using a new hybrid quadrupole/travelling wave IMS/oa-ToF instrument. Int. J. Mass Spectrom. 2007, 261, 1.
40. K. Thalassinos, M. Grabenauer, S. E. Slade, G. R. Hilton, M. T. Bowers, J. H. Scrivens,. Characterization of phosphorylated peptides using traveling wave-based and drift cell ion mobility mass spectrometry. Anal. Chem. 2009, 81, 248.
41. K. Pagel, D. J. Harvey,. Ion mobility mass spectrometry of complex carbohydrates-collision cross sections of sodiated N-linked glycans. Anal. Chem. 2013, 85, 5138.
42. D. J. Harvey, A. H. Merry, L. Royle, M. P. Campbell, R. A. Dwek, P. M. Rudd,. Proposal for a standard system for drawing structural diagrams of N- and O-linked carbohydrates and related compounds. Proteomics 2009, 9, 3796.