Cited by 395Glycosylation and Glycoproteins ResearchMass Spectrometry Techniques and ApplicationsAdvanced Proteomics Techniques and Applications

Mass spectrometry approaches to glycomic and glycoproteomic analyses

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Ruhaak, L. Renee, Xu, Gege, Li, Qiongyu, Goonatilleke, Elisha, Lebrilla, Carlito B.·2018·Chemical Reviews

Abstract

Glycomic and glycoproteomic analyses involve the characterization of oligosaccharides (glycans) conjugated to proteins. Glycans are produced through a complicated nontemplate driven process involving the competition of enzymes that extend the nascent chain. The large diversity of structures, the variations in polarity of the individual saccharide residues, and the poor ionization efficiencies of glycans all conspire to make the analysis arguably much more difficult than any other biopolymer. Furthermore, the large number of glycoforms associated with a specific protein site makes it more difficult to characterize than any post-translational modification. Nonetheless, there have been significant progress, and advanced separation and mass spectrometry methods have been at its center and the main reason for the progress. While glycomic and glycoproteomic analyses are still typically available only through highly specialized laboratories, new software and workflow is making it more accessible. This review focuses on the role of mass spectrometry and separation methods in advancing glycomic and glycoproteomic analyses. It describes the current state of the field and progress toward making it more available to the larger scientific community.

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  • MALDI and ESI are soft ionisation techniques that now dominate in the MS field.

    “Matrix-assisted laser desorption/ionisation (MALDI) and electrospray ionisation (ESI) are ‘soft ionisation' techniques, which now dominate in the MS field [142,145].”

    From Glycoengineering Chinese hamster ovary cells: a short history (2021) · cites this paper as [142]

    The “Ionization Considerations” section describes soft ionization techniques as normally used for glycan and glycopeptide analyses and says MALDI and ESI are the most widely used ionization methods in that context. It does not establish that they dominate the entire MS field, as the citing sentence claims. (LLM, conf=0.86)

    Experimental — accuracy not yet measured
  • Mass spectrometry-based techniques have dominated the glycomics and glycoproteomics fields for decades because of their high sensitivity and ability to characterise complex heterogeneous mixtures, especially when combined with upstream separation techniques such as liquid chromatography.

    “Mass spectrometry (MS)-based techniques, the experimental workflow for which is outlined in Figure 3, have dominated the glycomics and glycoproteomics fields for decades because of its high sensitivity and ability to characterise complex heterogeneous mixtures, especially when combined with upstream separation techniques such as liquid chromatography [142].”

    From Glycoengineering Chinese hamster ovary cells: a short history (2021) · cites this paper as [142]

    The Introduction (page unavailable) says MS has been central to glycomic and glycoproteomic analysis and describes its use with HPLC and UPLC. The instrumentation section (page unavailable) supports the sensitivity claim, while the separation-methods section explains why LC helps analyze heterogeneous glycan samples. The copy does not establish that MS dominated both fields for decades. (LLM, conf=0.82)

    Experimental — accuracy not yet measured

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  1. [1]Akan I; Olivier-Van Stichelen S; Bond MR; Hanover JA Nutrient-driven O-GlcNAc in proteostasis and neurodegeneration. J. Neurochem 2018, 144, 7– 34. 29049853 PMC5735008
  2. [2]Spiro RG Protein glycosylation: nature, distribution, enzymatic formation, and disease implications of glycopeptide bonds. Glycobiology 2002, 12, 43R– 56R. 12042244
  3. [3]Ly M; Leach FE 3rd; Laremore TN; Toida T; Amster IJ; Linhardt RJ The proteoglycan bikunin has a defined sequence. Nat. Chem. Biol 2011, 7, 827– 833. 21983600 PMC3197799
  4. [4]Ma JF; Hart GW O-GlcNAc profiling: from proteins to proteomes. Clin. Proteomics 2014, 11, 8. 24593906 PMC4015695
  5. [5]Staples GO; Zaia J Analysis of Glycosaminoglycans Using Mass Spectrometry. Curr. Proteomics 2011, 8, 325– 336. 25705143 PMC4334465
  6. [6]Laine RA A calculation of all possible oligosaccharide isomers both branched and linear yields 1.05 × 10(12) structures for a reducing hexasaccharide: the Isomer Barrier to development of single-method saccharide sequencing or synthesis systems. Glycobiology 1994, 4, 759– 767. 7734838
  7. [7]German JB; Freeman SL; Lebrilla CB; Mills DA Human milk oligosaccharides: evolution, structures and bioselectivity as substrates for intestinal bacteria. Nestle Nutr Workshop Ser. Pediatr Program 2008, 62, 205– 218 discussion 218–222. PMC2861563 18626202
  8. [8]Kronewitter SR; An HJ; de Leoz ML; Lebrilla CB; Miyamoto S; Leiserowitz GS The development of retrosynthetic glycan libraries to profile and classify the human serum N-linked glycome. Proteomics 2009, 9, 2986– 2994. 19452454 PMC2758495
  9. [9]Song T; Aldredge D; Lebrilla CB A Method for In-Depth Structural Annotation of Human Serum Glycans That Yields Biological Variations. Anal. Chem 2015, 87, 7754– 7762. 26086522 PMC5444872
  10. [10]Wu S; Grimm R; German JB; Lebrilla CB Annotation and structural analysis of sialylated human milk oligosaccharides. J. Proteome Res 2011, 10, 856– 868. 21133381 PMC3033989
  11. [11]Wu S; Tao N; German JB; Grimm R; Lebrilla CB Development of an annotated library of neutral human milk oligosaccharides. J. Proteome Res 2010, 9, 4138– 4151. 20578730 PMC2919513
  12. [12]Huang J; Guerrero A; Parker E; Strum JS; Smilowitz JT; German JB; Lebrilla CB Site-specific glycosylation of secretory immunoglobulin A from human colostrum. J. Proteome Res 2015, 14, 1335– 1349. 25629924 PMC5519350
  13. [13]Omtvedt LA; Royle L; Husby G; Sletten K; Radcliffe CM; Harvey DJ; Dwek RA; Rudd PM Glycan analysis of monoclonal antibodies secreted in deposition disorders indicates that subsets of plasma cells differentially process IgG glycans. Arthritis Rheum. 2006, 54, 3433– 3440. 17075835
  14. [14]Ruhaak LR; Barkauskas DA; Torres J; Cooke CL; Wu LD; Stroble C; Ozcan S; Williams CC; Camorlinga M; Rocke DM; The Serum Immunoglobulin G Glycosylation Signature of Gastric Cancer. EuPa Open Proteomics 2015, 6, 1– 9. 25685702 PMC4322429
  15. [15]An HJ; Tillinghast JS; Woodruff DL; Rocke DM; Lebrilla CB A new computer program (GlycoX) to determine simultaneously the glycosylation sites and oligosaccharide heterogeneity of glycoproteins. J. Proteome Res 2006, 5, 2800– 2808. 17022651
  16. [16]Moremen KW; Tiemeyer M; Nairn AV Vertebrate protein glycosylation: diversity, synthesis and function. Nat. Rev. Mol. Cell Biol 2012, 13, 448– 462. 22722607 PMC3934011
  17. [17]Schachter H The joys of HexNAc. The synthesis and function of N-and O-glycan branches. Glycoconjugate J. 2000, 17, 465– 483. 11421343
  18. [18]You X; Qin H; Ye M Recent advances in methods for the analysis of protein o-glycosylation at proteome level. J. Sep. Sci 2018, 41, 248– 261. 28988430
  19. [19]Cao L; Qu Y; Zhang ZR; Wang Z; Prytkova I; Wu S Intact glycopeptide characterization using mass spectrometry. Expert Rev. Proteomics 2016, 13, 513– 522. 27140194 PMC4955807
  20. [20]Hong Q; Ruhaak LR; Stroble C; Parker E; Huang J; Maverakis E; Lebrilla CB A Method for Comprehensive Glycosite-Mapping and Direct Quantitation of Serum Glycoproteins. J. Proteome Res 2015, 14, 5179– 5192. 26510530 PMC4670571
  21. [21]Yang N; Goonatilleke E; Park D; Song T; Fan G; Lebrilla CB Quantitation of Site-Specific Glycosylation in Manufactured Recombinant Monoclonal Antibody Drugs. Anal. Chem 2016, 88, 7091– 7100. 27311011 PMC4955800
  22. [22]James P Protein identification in the post-genome era: the rapid rise of proteomics. Q. Rev. Biophys 1997, 30, 279– 331. 9634650
  23. [23]Harvey DJ Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update covering the period 1999–2000. Mass Spectrom. Rev 2006, 25, 595– 662. 16642463
  24. [24]Harvey DJ Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2003–2004. Mass Spectrom. Rev 2009, 28, 273– 361. 18825656 PMC7168468
  25. [25]Harvey DJ Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for the period 2005–2006. Mass Spectrom. Rev 2011, 30, 1– 100. 20222147
  26. [26]Harvey DJ Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2007–2008. Mass Spectrom. Rev 2012, 31, 183– 311. 21850673
  27. [27]Harvey DJ Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for 2009–2010. Mass Spectrom. Rev 2015, 34, 268– 422. 24863367 PMC7168572
  28. [28]Mulagapati S; Koppolu V; Raju TS Decoding of O-Linked Glycosylation by Mass Spectrometry. Biochemistry 2017, 56, 1218– 1226. 28196325
  29. [29]Banazadeh A; Veillon L; Wooding KM; Zabet-Moghaddam M; Mechref Y Recent advances in mass spectrometric analysis of glycoproteins. Electrophoresis 2017, 38, 162– 189. 27757981 PMC5221507
  30. [30]Kailemia MJ; Ruhaak LR; Lebrilla CB; Amster IJ Oligosaccharide analysis by mass spectrometry: a review of recent developments. Anal. Chem 2014, 86, 196– 212. 24313268 PMC3924431
  31. [31]Palaniappan KK; Bertozzi CR Chemical Glycoproteomics. Chem. Rev 2016, 116, 14277– 14306. 27960262 PMC5327817
  32. [32]Xu G; Davis JC; Goonatilleke E; Smilowitz JT; German JB; Lebrilla CB Absolute Quantitation of Human Milk Oligosaccharides Reveals Phenotypic Variations during Lactation. J. Nutr 2017, 147, 117– 124. 27798342 PMC5177733
  33. [33]Zhang H; Wang Z; Stupak J; Ghribi O; Geiger JD; Liu QY; Li J Targeted glycomics by selected reaction monitoring for highly sensitive glycan compositional analysis. Proteomics 2012, 12, 2510– 2522. 22821818 PMC3836389
  34. [34]Park Y; Lebrilla CB Application of Fourier transform ion cyclotron resonance mass spectrometry to oligosaccharides. Mass Spectrom. Rev 2005, 24, 232– 264. 15389860
  35. [35]An HJ; Lebrilla CB A glycomics approach to the discovery of potential cancer biomarkers. Methods Mol. Biol 2010, 600, 199– 213. 19882130
  36. [36]Totten SM; Feasley CL; Bermudez A; Pitteri SJ Parallel Comparison of N-Linked Glycopeptide Enrichment Techniques Reveals Extensive Glycoproteomic Analysis of Plasma Enabled by SAX-ERLIC. J. Proteome Res 2017, 16, 1249– 1260. 28199111
  37. [37]Wang X; Emmett MR; Marshall AG Liquid chromatography electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric characterization of N-linked glycans and glycopeptides. Anal. Chem 2010, 82, 6542– 6548. 20586410
  38. [38]Hong Q; Lebrilla CB; Miyamoto S; Ruhaak LR Absolute quantitation of immunoglobulin G and its glycoforms using multiple reaction monitoring. Anal. Chem 2013, 85, 8585– 8593. 23944609 PMC3857154
  39. [39]Ruhaak LR; Taylor SL; Miyamoto S; Kelly K; Leiserowitz GS; Gandara D; Lebrilla CB; Kim K Chip-based nLC-TOF-MS is a highly stable technology for large-scale high-throughput analyses. Anal. Bioanal. Chem 2013, 405, 4953– 4958. 23525540 PMC3640767
  40. [40]Hong Q; Ruhaak LR; Totten SM; Smilowitz JT; German JB; Lebrilla CB Label-free absolute quantitation of oligosaccharides using multiple reaction monitoring. Anal. Chem 2014, 86, 2640– 2647. 24502421 PMC3983013
  41. [41]Penn SG; Cancilla MT; Lebrilla CB Collision-induced dissociation of branched oligosaccharide ions with analysis and calculation of relative dissociation thresholds. Anal. Chem 1996, 68, 2331– 2339. 8686926
  42. [42]Ngoka LC; Gal JF; Lebrilla CB Effects of Cations and Charge Types on the Metastable Decay-Rates of Oligosaccharides. Anal. Chem 1994, 66, 692– 698. 8154590
  43. [43]Spengler B; Kirsch D; Kaufmann R; Cotter RJ Metastable Decay of Peptides and Proteins in Matrix-Assisted Laser-Desorption Mass-Spectrometry. Rapid Commun. Mass Spectrom 1991, 5, 198– 202.
  44. [44]Zhang JH; LaMotte LT; Dodds ED; Lebrilla CB Atmospheric pressure MALDI Fourier transform mass spectrometry of labile oligosaccharides. Anal. Chem 2005, 77, 4429– 4438. 16013856
  45. [45]An HJ; Miyamoto S; Lancaster KS; Kirmiz C; Li B; Lam KS; Leiserowitz GS; Lebrilla CB Profiling of glycans in serum for the discovery of potential biomarkers for ovarian cancer. J. Proteome Res 2006, 5, 1626– 1635. 16823970
  46. [46]Budnik BA; Lee RS; Steen JAJ Global methods for protein glycosylation analysis by mass spectrometry. Biochim. Biophys. Acta, Proteins Proteomics 2006, 1764, 1870– 1880. 17118724
  47. [47]Dongre AR; Wysocki VH Linkage Position Determination of Lithium-Cationized Disaccharides by Surface-Induced Dissociation Tandem Mass-Spectrometry. Org. Mass Spectrom 1994, 29, 700– 702.
  48. [48]An HJ; Lebrilla CB Structure elucidation of native N- and O-linked glycans by tandem mass spectrometry (tutorial). Mass Spectrom. Rev 2011, 30, 560– 578. 21656841
  49. [49]Wuhrer M; Deelder AM; van der Burgt YE Mass spectrometric glycan rearrangements. Mass Spectrom. Rev 2011, 30, 664– 680. 21560141
  50. [50]Dell A Preparation and desorption mass spectrometry of permethyl and peracetyl derivatives of oligosaccharides. Methods Enzymol. 1990, 193, 647– 660. 2074840
  51. [51]Russell SC; Czerwieniec G; Lebrilla C; Steele P; Riot V; Coffee K; Frank M; Gard EE Achieving high detection sensitivity (14 zmol) of biomolecular ions in bioaerosol mass spectrometry. Anal. Chem 2005, 77, 4734– 4741. 16053283
  52. [52]Prien JM; Ashline DJ; Lapadula AJ; Zhang H; Reinhold VN The High Mannose Glycans from Bovine Ribonuclease B Isomer Characterization by Ion Trap MS. J. Am. Soc. Mass Spectrom 2009, 20, 539– 556. 19181540 PMC2702475
  53. [53]Seipert RR; Dodds ED; Clowers BH; Beecroft SM; German JB; Lebrilla CB Factors that influence fragmentation behavior of N-linked glycopeptide ions. Anal. Chem 2008, 80, 3684– 3692. 18363335 PMC6551518
  54. [54]Seipert RR; Dodds ED; Lebrilla CB Exploiting Differential Dissociation Chemistries of O-Linked Glycopeptide Ions for the Localization of Mucin-Type Protein Glycosylation. J. Proteome Res 2009, 8, 493– 501. 19067536 PMC2680678
  55. [55]Haag AM Mass Analyzers and Mass Spectrometers. Adv. Exp. Med. Biol 2016, 919, 157– 169. 27975216
  56. [56]Sobott F; Watt SJ; Smith J; Edelmann MJ; Kramer HB; Kessler BM Comparison of CID Versus ETD Based MS/MS Fragmentation for the Analysis of Protein Ubiquitination. J. Am. Soc. Mass Spectrom 2009, 20, 1652– 1659. 19523847
  57. [57]Mechref Y Use of CID/ETD Mass Spectrometry to Analyze Glycopeptides. Curr. Protoc. Protein Sci 2012, 12, 12.11. PMC3673024 22470127
  58. [58]Alley WR; Mechref Y; Novotny MV Characterization of glycopeptides by combining collision-induced dissociation and electron-transfer dissociation mass spectrometry data. Rapid Commun. Mass Spectrom 2009, 23, 161– 170. 19065542
  59. [59]Ford KL; Zeng W; Heazlewood JL; Bacic A Characterization of protein N-glycosylation by tandem mass spectrometry using complementary fragmentation techniques. Front. Plant Sci 2015, 6, 674. 26379696 PMC4551829
  60. [60]Windwarder M; Yelland T; Djordjevic S; Altmann F Detailed characterization of the O-linked glycosylation of the neuropilin-1 c/MAM-domain. Glycoconjugate J. 2016, 33, 387– 397. 26059692
  61. [61]Moh ESX; Lin CH; Thaysen-Andersen M; Packer NH Site-Specific N-Glycosylation of Recombinant Pentameric and Hexameric Human IgM. J. Am. Soc. Mass Spectrom 2016, 27, 1143– 1155. 27038031
  62. [62]Frese CK; Altelaar AFM; van den Toorn H; Nolting D; Griep-Raming J; Heck AJR; Mohammed S Toward Full Peptide Sequence Coverage by Dual Fragmentation Combining Electron-Transfer and Higher-Energy Collision Dissociation Tandem Mass Spectrometry. Anal. Chem 2012, 84, 9668– 9673. 23106539
  63. [63]Parker BL; Thaysen-Andersen M; Fazakerley DJ; Holliday M; Packer NH; James DE Terminal galactosylation and sialylation switching on membrane glycoproteins upon TNF-alpha-induced insulin resistance in adipocytes. Mol. Cell. Proteomics 2016, 15, 141– 153. 26537798 PMC4762517
  64. [64]Yu Q; Wang B; Chen Z; Urabe G; Glover MS; Shi X; Guo L-W; Kent KC; Li L Electron-Transfer/Higher-Energy Collision Dissociation (EThcD)-Enabled Intact Glycopeptide/Glycoproteome Characterization. J. Am. Soc. Mass Spectrom 2017, 28, 1751– 1764. 28695533 PMC5711575
  65. [65]Håkansson K; Cooper HJ; Emmett MR; Costello CE; Marshall AG; Nilsson CL Electron capture dissociation and infrared multiphoton dissociation MS/MS of an N-glycosylated tryptic peptide to yield complementary sequence information. Anal. Chem 2001, 73, 4530– 4536. 11575803
  66. [66]Manri N; Satake H; Kaneko A; Hirabayashi A; Baba T; Sakamoto T Glycopeptide Identification Using Liquid-Chromatography-Compatible Hot Electron Capture Dissociation in a Radio-Frequency-Quadrupole Ion Trap. Anal. Chem 2013, 85, 2056– 2063. 23317463
  67. [67]Yu X; Jiang Y; Chen Y; Huang Y; Costello CE; Lin C Detailed Glycan Structural Characterization by Electronic Excitation Dissociation. Anal. Chem 2013, 85, 10017– 10021. 24080071 PMC3851312
  68. [68]Brodbelt JS Photodissociation mass spectrometry: new tools for characterization of biological molecules. Chem. Soc. Rev 2014, 43, 2757– 2783. 24481009 PMC3966968
  69. [69]Zhang L; Reilly JP Extracting Both Peptide Sequence and Glycan Structural Information by 157 nm Photodissociation of N-Linked Glycopeptides. J. Proteome Res 2009, 8, 734– 742. 19113943 PMC2654178
  70. [70]Madsen JA; Ko BJ; Xu H; Iwashkiw JA; Robotham SA; Shaw JB; Feldman MF; Brodbelt JS Concurrent automated sequencing of the glycan and peptide portions of O-linked glycopeptide anions by ultraviolet photodissociation mass spectrometry. Anal. Chem 2013, 85, 9253– 9261. 24006841 PMC3816934
  71. [71]Ko BJ; Brodbelt JS Comparison of Glycopeptide Fragmentation by Collision Induced Dissociation and Ultraviolet Photodissociation. Int. J. Mass Spectrom 2015, 377, 385– 392. 25844059 PMC4379704
  72. [72]Ko BJ; Brodbelt JS 193 nm Ultraviolet Photodissociation of Deprotonated Sialylated Oligosaccharides. Anal. Chem 2011, 83, 8192– 8200. 21913695
  73. [73]Cotham VC; Brodbelt JS Characterization of Therapeutic Monoclonal Antibodies at the Subunit-Level using Middle-Down 193 nm Ultraviolet Photodissociation. Anal. Chem 2016, 88, 4004– 4013. 26947921
  74. [74]Ji Y; Xiong Z; Huang G; Liu J; Zhang Z; Liu Z; Ou J; Ye M; Zou H Efficient enrichment of glycopeptides using metal-organic frameworks by hydrophilic interaction chromatography. Analyst 2014, 139, 4987– 4993. 25110774
  75. [75]Sandoval WN; Arellano F; Arnott D; Raab H; Vandlen R; Lill JR Rapid removal of N-linked oligosaccharides using microwave assisted enzyme catalyzed deglycosylation. Int. J. Mass Spectrom 2007, 259, 117– 123.
  76. [76]Ren X; Bai H; Pan Y; Tong W; Qin P; Yan H; Deng S; Zhong R; Qin W; Qian X A graphene oxide-based immobilized PNGase F reagent for highly efficient N-glycan release and MALDI-TOF MS profiling. Anal. Methods 2014, 6, 2518– 2525.
  77. [77]Tretter V; Altmann F; Marz L Peptide-N4-(N-Acetyl-Beta-Glucosaminyl)Asparagine Amidase-F Cannot Release Glycans with Fucose Attached Alpha-1-]3 to the Asparagine-Linked N-Acetylglucosamine Residue. Eur. J. Biochem 1991, 199, 647– 652. 1868849
  78. [78]Wang T; Cai ZP; Gu XQ; Ma HY; Du YM; Huang K; Voglmeir J; Liu L Discovery and characterization of a novel extremely acidic bacterial N-glycanase with combined advantages of PNGase F and A. Biosci. Rep 2014, 34, 673– 684. PMC4231336 25294009
  79. [79]Maley F; Trimble RB; Tarentino AL; Plummer TH Characterization of Glycoproteins and Their Associated Oligosaccharides through the Use of Endoglycosidases. Anal. Biochem 1989, 180, 195– 204. 2510544
  80. [80]Brooks MM; Savage AV The substrate specificity of the enzyme endo-alpha-N-acetyl-D-galactosaminidase from Diplococcus pneumonia. Glycoconjugate J. 1997, 14, 183– 190. 9111135
  81. [81]Kozak RP; Royle L; Gardner RA; Bondt A; Fernandes DL; Wuhrer M Improved nonreductive O-glycan release by hydrazinolysis with ethylenediaminetetraacetic acid addition. Anal. Biochem 2014, 453, 29– 37. 24613257
  82. [82]Merry AH; Neville DCA; Royle L; Matthews B; Harvey DJ; Dwek RA; Rudd PM Recovery of intact 2-aminobenzamide-labeled O-glycans released from glycoproteins by hydrazinolysis. Anal. Biochem 2002, 304, 91– 99. 11969192
  83. [83]Song X; Ju H; Lasanajak Y; Kudelka MR; Smith DF; Cummings RD Oxidative release of natural glycans for functional glycomics. Nat. Methods 2016, 13, 528– 534. 27135973 PMC4887297
  84. [84]Goso Y; Sugaya T; Ishihara K; Kurihara M Comparison of Methods to Release Mucin-Type O-Glycans for Glycomic Analysis. Anal. Chem 2017, 89, 8870– 8876. 28723077
  85. [85]Ruhaak LR; Zauner G; Huhn C; Bruggink C; Deelder AM; Wuhrer M Glycan labeling strategies and their use in identification and quantification. Anal. Bioanal. Chem 2010, 397, 3457– 3481. 20225063 PMC2911528
  86. [86]Pabst M; Kolarich D; Poltl G; Dalik T; Lubec G; Hofinger A; Altmann F Comparison of fluorescent labels for oligosaccharides and introduction of a new postlabeling purification method. Anal. Biochem 2009, 384, 263– 273. 18940176
  87. [87]Anumula KR Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Anal. Biochem 2006, 350, 1– 23. 16271261
  88. [88]Honda S; Akao E; Suzuki S; Okuda M; Kakehi K; Nakamura J High-Performance Liquid-Chromatography of Reducing Carbohydrates as Strongly Ultraviolet-Absorbing and Electrochemically Sensitive 1-Phenyl-3-Methyl-5-Pyrazolone Derivatives. Anal. Biochem 1989, 180, 351– 357. 2817366
  89. [89]Kakehi K; Suzuki S; Honda S; Lee YC Precolumn labeling of reducing carbohydrates with 1-(p-methoxy)phenyl-3-methyl-5-pyrazolone: analysis of neutral and sialic acid-containing oligosaccharides found in glycoproteins. Anal. Biochem 1991, 199, 256– 268. 1725951
  90. [90]Gil GC; Kim YG; Kim BG A relative and absolute quantification of neutral N-linked oligosaccharides using modification with carboxymethyl trimethylammonium hydrazide and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal. Biochem 2008, 379, 45– 59. 18498755
  91. [91]Jang KS; Kim YG; Gil GC; Park SH; Kim BG Mass spectrometric quantification of neutral and sialylated N-glycans from a recombinant therapeutic glycoprotein produced in the two Chinese hamster ovary cell lines. Anal. Biochem 2009, 386, 228– 236. 19135424
  92. [92]Jiao J; Yang L; Zhang Y; Lu H Hydrazinonicotinic acid derivatization for selective ionization and improved glycan structure characterization by MALDI-MS. Analyst 2015, 140, 5475– 5480. 26133099
  93. [93]Zhao MZ; Zhang YW; Yuan F; Deng Y; Liu JX; Zhou YL; Zhang XX Hydrazino-s-triazine based labelling reagents for highly sensitive glycan analysis via liquid chromatography-electrospray mass spectrometry. Talanta 2015, 144, 992– 997. 26452918
  94. [94]Zhang Y; Peng Y; Bin Z; Wang H; Lu H Highly specific purification of N-glycans using phosphate-based derivatization as an affinity tag in combination with Ti(4+)-SPE enrichment for mass spectrometric analysis. Anal. Chim. Acta 2016, 934, 145– 151. 27506354
  95. [95]Li L; Jiao J; Cai Y; Zhang Y; Lu H Fluorinated carbon tag derivatization combined with fluorous solid-phase extraction: a new method for the highly sensitive and selective mass spectrometric analysis of glycans. Anal. Chem 2015, 87, 5125– 5131. 25884104
  96. [96]Jiang K; Zhu H; Xiao C; Liu D; Edmunds G; Wen L; Ma C; Li J; Wang PG Solid-phase reductive amination for glycomic analysis. Anal. Chim. Acta 2017, 962, 32– 40. 28231878
  97. [97]Wang C; Fan W; Zhang P; Wang Z; Huang L One-pot nonreductive O-glycan release and labeling with 1-phenyl-3-methyl-5-pyrazolone followed by ESI-MS analysis. Proteomics 2011, 11, 4229– 4242. 21956845
  98. [98]Wang C; Zhang P; Jin W; Li L; Qiang S; Zhang Y; Huang L; Wang Z Quantitative O-glycomics based on improvement of the one-pot method for nonreductive O-glycan release and simultaneous stable isotope labeling with 1-(d0/d5)phenyl-3-methyl-5-pyrazolone followed by mass spectrometric analysis. J. Proteomics 2017, 150, 18– 30. 27585995
  99. [99]Yang S; Hoti N; Yang W; Liu Y; Chen L; Li S; Zhang H Simultaneous analyses of N-linked and O-linked glycans of ovarian cancer cells using solid-phase chemoenzymatic method. Clin. Proteomics 2017, 14, 3. 28100988 PMC5237303
  100. [100]Yang S; Hu Y; Sokoll L; Zhang H Simultaneous quantification of N- and O-glycans using a solid-phase method. Nat. Protoc 2017, 12, 1229– 1244. 28518173 PMC5877797
  101. [101]Ciucanu I; Kerek F A Simple and Rapid Method for the Permethylation of Carbohydrates. Carbohydr. Res 1984, 131, 209– 217.
  102. [102]Ciucanu I; Costello CE Elimination of oxidative degradation during the per-O-methylation of carbohydrates. J. Am. Chem. Soc 2003, 125, 16213– 16219. 14692762
  103. [103]Kang P; Mechref Y; Klouckova I; Novotny MV Solid-phase permethylation of glycans for mass spectrometric analysis. Rapid Commun. Mass Spectrom 2005, 19, 3421– 3428. 16252310 PMC1470644
  104. [104]Shubhakar A; Kozak RP; Reiding KR; Royle L; Spencer DI; Fernandes DL; Wuhrer M Automated High-Throughput Permethylation for Glycosylation Analysis of Biologics Using MALDI-TOF-MS. Anal. Chem 2016, 88, 8562– 8569. 27479043
  105. [105]Hu Y; Borges CR A spin column-free approach to sodium hydroxide-based glycan permethylation. Analyst 2017, 142, 2748– 2759. 28635997 PMC5973876
  106. [106]Wheeler SF; Domann P; Harvey DJ Derivatization of sialic acids for stabilization in matrix-assisted laser desorption/ionization mass spectrometry and concomitant differentiation of alpha(2–> 3)- and alpha(2–> 6)-isomers. Rapid Commun. Mass Spectrom 2009, 23, 303– 312. 19089860
  107. [107]Alley WR; Novotny MV Glycomic Analysis of Sialic Acid Linkages in Glycans Derived from Blood Serum Glycoproteins. J. Proteome Res 2010, 9, 3062– 3072. 20345175 PMC2922414
  108. [108]Tousi F; Bones J; Hancock WS; Hincapie M Differential chemical derivatization integrated with chromatographic separation for analysis of isomeric sialylated N-glycans: a nano-hydrophilic interaction liquid chromatography-MS platform. Anal. Chem 2013, 85, 8421– 8428. 23901877
  109. [109]Reiding KR; Blank D; Kuijper DM; Deelder AM; Wuhrer M High-throughput profiling of protein N-glycosylation by MALDI-TOF-MS employing linkage-specific sialic acid esterification. Anal. Chem 2014, 86, 5784– 5793. 24831253
  110. [110]de Haan N; Reiding KR; Haberger M; Reusch D; Falck D; Wuhrer M Linkage-specific sialic acid derivatization for MALDI-TOF-MS profiling of IgG glycopeptides. Anal. Chem 2015, 87, 8284– 8291. 26191964
  111. [111]Yang S; Jankowska E; Kosikova M; Xie H; Cipollo J Solid-Phase Chemical Modification for Sialic Acid Linkage Analysis: Application to Glycoproteins of Host Cells Used in Influenza Virus Propagation. Anal. Chem 2017, 89, 9508– 9517. 28792205
  112. [112]Bladergroen MR; Reiding KR; Hipgrave Ederveen ALH; Vreeker GCM; Clerc F; Holst S; Bondt A; Wuhrer M; van der Burgt YEM Automation of High-Throughput Mass Spectrometry-Based Plasma N-Glycome Analysis with Linkage-Specific Sialic Acid Esterification. J. Proteome Res 2015, 14, 4080– 4086. 26179816
  113. [113]Li H; Gao W; Feng X; Liu BF; Liu X MALDI-MS analysis of sialylated N-glycan linkage isomers using solid-phase two step derivatization method. Anal. Chim. Acta 2016, 924, 77– 85. 27181647
  114. [114]Jiang K; Zhu H; Li L; Guo Y; Gashash E; Ma C; Sun X; Li J; Zhang L; Wang PG Sialic acid linkage-specific permethylation for improved profiling of protein glycosylation by MALDI-TOF MS. Anal. Chim. Acta 2017, 981, 53– 61. 28693729 PMC5953179
  115. [115]Nishikaze T; Tsumoto H; Sekiya S; Iwamoto S; Miura Y; Tanaka K Differentiation of Sialyl Linkage Isomers by One-Pot Sialic Acid Derivatization for Mass Spectrometry-Based Glycan Profiling. Anal. Chem 2017, 89, 2353– 2360. 28194959
  116. [116]Walker SH; Carlisle BC; Muddiman DC Systematic comparison of reverse phase and hydrophilic interaction liquid chromatography platforms for the analysis of N-linked glycans. Anal. Chem 2012, 84, 8198– 8206. 22954204 PMC3689152
  117. [117]Alley WR; Madera M; Mechref Y; Novotny MV Chip-based Reversed-phase Liquid Chromatography-Mass Spectrometry of Permethylated N-Linked Glycans: A Potential Methodology for Cancer-biomarker Discovery. Anal. Chem 2010, 82, 5095– 5106. 20491449 PMC2910595
  118. [118]Hu Y; Shihab T; Zhou S; Wooding K; Mechref Y LC-MS/MS of permethylated N-glycans derived from model and human blood serum glycoproteins. Electrophoresis 2016, 37, 1498– 1505. 26959726 PMC4964794
  119. [119]Ritamo I; Rabina J; Natunen S; Valmu L Nanoscale reversed-phase liquid chromatography-mass spectrometry of permethylated N-glycans. Anal. Bioanal. Chem 2013, 405, 2469– 2480. 23307132
  120. [120]Vreeker GC; Wuhrer M Reversed-phase separation methods for glycan analysis. Anal. Bioanal. Chem 2017, 409, 359– 378. 27888305 PMC5203856
  121. [121]Bereman MS; Williams TI; Muddiman DC 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. 19113831 PMC3739471
  122. [122]Bereman MS; Young DD; Deiters A; Muddiman DC Development of a Robust and High Throughput Method for Profiling N-Linked Glycans Derived from Plasma Glycoproteins by NanoLC-FTICR Mass Spectrometry. J. Proteome Res 2009, 8, 3764– 3770. 19435342 PMC3739297
  123. [123]Lam MP; Siu SO; Lau E; Mao X; Sun HZ; Chiu PC; Yeung WS; Cox DM; Chu IK Online coupling of reverse-phase and hydrophilic interaction liquid chromatography for protein and glycoprotein characterization. Anal. Bioanal. Chem 2010, 398, 791– 804. 20632160 PMC2939347
  124. [124]Ahn J; Bones J; Yu YQ; Rudd PM; Gilar M Separation of 2-aminobenzamide labeled glycans using hydrophilic interaction chromatography columns packed with 1.7μm sorbent. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci 2010, 878, 403– 408. 20036624
  125. [125]Saldova R; Asadi Shehni A; Haakensen VD; Steinfeld I; Hilliard M; Kifer I; Helland A; Yakhini Z; Borresen-Dale AL; Rudd PM Association of N-glycosylation with breast carcinoma and systemic features using high-resolution quantitative UPLC. J. Proteome Res 2014, 13, 2314– 2327. 24669823
  126. [126]Doherty M; Bones J; McLoughlin N; Telford JE; Harmon B; DeFelippis MR; Rudd PM An automated robotic platform for rapid profiling oligosaccharide analysis of monoclonal antibodies directly from cell culture. Anal. Biochem 2013, 442, 10– 18. 23872006
  127. [127]Zacharias LG; Hartmann AK; Song EH; Zhao JF; Zhu R; Mirzaei P; Mechref Y HILIC and ERLIC Enrichment of Glycopeptides Derived from Breast and Brain Cancer Cells. J. Proteome Res 2016, 15, 3624– 3634. 27533485 PMC5748158
  128. [128]Adamczyk B; Tharmalingam-Jaikaran T; Schomberg M; Szekrenyes A; Kelly RM; Karlsson NG; Guttman A; Rudd PM Comparison of separation techniques for the elucidation of IgG N-glycans pooled from healthy mammalian species. Carbohydr. Res 2014, 389, 174– 185. 24680513
  129. [129]Mauko L; Lacher NA; Pelzing M; Nordborg A; Haddad PR; Hilder EF Comparison of ZIC-HILIC and graphitized carbon-based analytical approaches combined with exoglycosidase digestions for analysis of glycans from monoclonal antibodies. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci 2012, 911, 93– 104. 23217312
  130. [130]Palmisano G; Larsen MR; Packer NH; Thaysen-Andersen M Structural analysis of glycoprotein sialylation - part II: LC-MS based detection. RSC Adv. 2013, 3, 22706– 22726.
  131. [131]Hua S; An HJ; Ozcan S; Ro GS; Soares S; DeVere-White R; Lebrilla CB Comprehensive native glycan profiling with isomer separation and quantitation for the discovery of cancer biomarkers. Analyst 2011, 136, 3663– 3671. 21776491 PMC3331797
  132. [132]Hua S; Williams CC; Dimapasoc LM; Ro GS; Ozcan S; Miyamoto S; Lebrilla CB; An HJ; Leiserowitz GS Isomer-specific chromatographic profiling yields highly sensitive and specific potential N-glycan biomarkers for epithelial ovarian cancer. J. Chromatogr. A 2013, 1279, 58– 67. 23380366 PMC5628020
  133. [133]Anugraham M; Jacob F; Nixdorf S; Everest-Dass AV; Heinzelmann-Schwarz V; Packer NH Specific glycosylation of membrane proteins in epithelial ovarian cancer cell lines: glycan structures reflect gene expression and DNA methylation status. Mol. Cell. Proteomics 2014, 13, 2213– 2232. 24855066 PMC4159645
  134. [134]Park D; Brune KA; Mitra A; Marusina AI; Maverakis E; Lebrilla CB Characteristic Changes in Cell Surface Glycosylation Accompany Intestinal Epithelial Cell (IEC) Differentiation: High Mannose Structures Dominate the Cell Surface Glycome of Undifferentiated Enterocytes. Mol. Cell. Proteomics 2015, 14, 2910– 2921. 26355101 PMC4638035
  135. [135]Nwosu CC; Aldredge DL; Lee H; Lerno LA; Zivkovic AM; German JB; Lebrilla CB Comparison of the Human and Bovine Milk N-Glycome via High-Performance Microfluidic Chip Liquid Chromatography and Tandem Mass Spectrometry. J. Proteome Res 2012, 11, 2912– 2924. 22439776 PMC3345083
  136. [136]Kronewitter SR; Marginean I; Cox JT; Zhao R; Hagler CD; Shukla AK; Carlson TS; Adkins JN; Camp DG II; Moore RJ; Polysialylated N-glycans identified in human serum through combined developments in sample preparation, separations, and electrospray ionization-mass spectrometry. Anal. Chem 2014, 86, 8700– 8710. 25118826 PMC4151788
  137. [138]Guttman A; Kerekgyarto M; Jarvas G Effect of Separation Temperature on Structure Specific Glycan Migration in Capillary Electrophoresis. Anal. Chem 2015, 87, 11630– 11634. 26544759
  138. [139]Szigeti M; Guttman A High-Resolution Glycan Analysis by Temperature Gradient Capillary Electrophoresis. Anal. Chem 2017, 89, 2201– 2204. 28192904
  139. [140]Feng HT; Su M; Rifai FN; Li P; Li SF Parallel analysis and orthogonal identification of N-glycans with different capillary electrophoresis mechanisms. Anal. Chim. Acta 2017, 953, 79– 86. 28010746
  140. [142]Lapainis T; Rubakhin SS; Sweedler JV Capillary electrophoresis with electrospray ionization mass spectrometric detection for single-cell metabolomics. Anal. Chem 2009, 81, 5858– 5864. 19518091 PMC2810313
  141. [143]Smith RD; Barinaga CJ; Udseth HR Improved Electrospray Ionization Interface for Capillary Zone Electrophoresis - Mass-Spectrometry. Anal. Chem 1988, 60, 1948– 1952.
  142. [144]Olivares JA; Nguyen NT; Yonker CR; Smith RD Online Mass-Spectrometric Detection for Capillary Zone Electrophoresis. Anal. Chem 1987, 59, 1230– 1232.
  143. [145]Chang YZ; Her GR Sheathless capillary electrophoresis/electrospray mass spectrometry using a carbon-coated fused silica capillary. Anal. Chem 2000, 72, 626– 630. 10695152
  144. [146]Maxwell EJ; Zhong X; Zhang H; van Zeijl N; Chen DD Decoupling CE and ESI for a more robust interface with MS. Electrophoresis 2010, 31, 1130– 1137. 20196027
  145. [148]Mellors JS; Gorbounov V; Ramsey RS; Ramsey JM Fully integrated glass microfluidic device for performing high-efficiency capillary electrophoresis and electrospray ionization mass spectrometry. Anal. Chem 2008, 80, 6881– 6887. 18698800 PMC3125599
  146. [149]Khatri K; Klein JA; Haserick JR; Leon DR; Costello CE; McComb ME; Zaia J Microfluidic Capillary Electrophoresis-Mass Spectrometry for Analysis of Monosaccharides, Oligosaccharides, and Glycopeptides. Anal. Chem 2017, 89, 6645– 6655. 28530388 PMC5554952
  147. [150]Gray CJ; Thomas B; Upton R; Migas LG; Eyers CE; Barran PE; Flitsch SL Applications of ion mobility mass spectrometry for high throughput, high resolution glycan analysis. Biochim. Biophys. Acta, Gen. Subj 2016, 1860, 1688– 1709. 26854953
  148. [151]Hofmann J; Pagel K Glycan Analysis by Ion Mobility-Mass Spectrometry. Angew. Chem., Int. Ed 2017, 56, 8342– 8349. 28436597
  149. [152]Clowers BH; Dwivedi P; Steiner WE; Hill HH Jr.; Bendiak B 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– 669. 15862767
  150. [153]Gabryelski W; Froese KL Rapid and sensitive differentiation of anomers, linkage, and position isomers of disaccharides using High-Field Asymmetric Waveform Ion Mobility Spectrometry (FAIMS). J. Am. Soc. Mass Spectrom 2003, 14, 265– 277. 12648934
  151. [154]Lu H; Zhang Y; Yang P Advancements in mass spectrometry-based glycoproteomics and glycomics. Natl. Sci. Rev 2016, 3, 345– 364.
  152. [155]Dwivedi P; Bendiak B; Clowers BH; Hill HH Jr 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– 1175. 17532226
  153. [156]Fenn LS; McLean JA Structural resolution of carbohydrate positional and structural isomers based on gas-phase ion mobility-mass spectrometry. Phys. Chem. Chem. Phys 2011, 13, 2196– 2205. 21113554
  154. [157]Isailovic D; Kurulugama RT; Plasencia MD; Stokes ST; Kyselova Z; Goldman R; Mechref Y; Novotny MV; Clemmer DE Profiling of human serum glycans associated with liver cancer and cirrhosis by IMS-MS. J. Proteome Res 2008, 7, 1109– 1117. 18237112 PMC3727278
  155. [158]Plasencia MD; Isailovic D; Merenbloom SI; Mechref Y; Clemmer DE Resolving and assigning N-linked glycan structural isomers from ovalbumin by IMS-MS. J. Am. Soc. Mass Spectrom 2008, 19, 1706– 1715. 18760624 PMC2626179
  156. [159]Zhu F; Lee S; Valentine SJ; Reilly JP; Clemmer DE Mannose7 glycan isomer characterization by IMS-MS/MS analysis. J. Am. Soc. Mass Spectrom 2012, 23, 2158– 2166. 23055077 PMC3515714
  157. [160]Pagel K; Harvey DJ Ion mobility-mass spectrometry of complex carbohydrates: collision cross sections of sodiated N-linked glycans. Anal. Chem 2013, 85, 5138– 5145. 23621517
  158. [161]Struwe WB; Pagel K; Benesch JLP; Harvey DJ; Campbell MP GlycoMob: an ion mobility-mass spectrometry collision cross section database for glycomics. Glycoconjugate J. 2016, 33, 399– 404. 26314736
  159. [162]Yamaguchi Y; Nishima W; Re S; Sugita Y 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– 2884. 23136018
  160. [163]Lareau NM; May JC; McLean JA Non-derivatized glycan analysis by reverse phase liquid chromatography and ion mobility-mass spectrometry. Analyst 2015, 140, 3335– 3338. 25737268 PMC4422766
  161. [164]Harvey DJ; Scarff CA; Edgeworth M; Crispin M; Scanlan CN; Sobott F; Allman S; Baruah K; Pritchard L; Scrivens JH Travelling wave ion mobility and negative ion fragmentation for the structural determination of N-linked glycans. Electrophoresis 2013, 34, 2368– 2378. 23712623
  162. [165]Gaye MM; Valentine SJ; Hu Y; Mirjankar N; Hammoud ZT; Mechref Y; Lavine BK; Clemmer DE Ion mobility-mass spectrometry analysis of serum N-linked glycans from esophageal adenocarcinoma phenotypes. J. Proteome Res 2012, 11, 6102– 6110. 23126309 PMC3534975
  163. [166]Seo Y; Schenauer MR; Leary JA Biologically Relevant Metal-Cation Binding Induces Conformational Changes in Heparin Oligosaccharides as Measured by Ion Mobility Mass Spectrometry. Int. J. Mass Spectrom 2011, 303, 191– 198. 21731426 PMC3124288
  164. [167]Zhu F; Glover MS; Shi H; Trinidad JC; Clemmer DE Populations of metal-glycan structures influence MS fragmentation patterns. J. Am. Soc. Mass Spectrom 2015, 26, 25– 35. 25315458 PMC4276451
  165. [168]Huang Y; Dodds ED Ion mobility studies of carbohydrates as group I adducts: isomer specific collisional cross section dependence on metal ion radius. Anal. Chem 2013, 85, 9728– 9735. 24033309
  166. [169]Huang Y; Dodds ED Ion-neutral collisional cross sections of carbohydrate isomers as divalent cation adducts and their electron transfer products. Analyst 2015, 140, 6912– 6921. 26225371
  167. [170]Morrison KA; Bendiak BK; Clowers BH Enhanced Mixture Separations of Metal Adducted Tetrasaccharides Using Frequency Encoded Ion Mobility Separations and Tandem Mass Spectrometry. J. Am. Soc. Mass Spectrom 2017, 28, 664– 677. 27796835
  168. [171]Zheng X; Zhang X; Schocker NS; Renslow RS; Orton DJ; Khamsi J; Ashmus RA; Almeida IC; Tang K; Costello CE; Enhancing glycan isomer separations with metal ions and positive and negative polarity ion mobility spectrometry-mass spectrometry analyses. Anal. Bioanal. Chem 2017, 409, 467– 476. 27604268 PMC5434874
  169. [172]Struwe WB; Benesch JL; Harvey DJ; Pagel K Collision cross sections of high-mannose N-glycans in commonly observed adduct states-identification of gas-phase conformers unique to [M-H] (−) ions. Analyst 2015, 140, 6799– 6803. 26159123
  170. [173]McDonnell LA; Heeren RM Imaging mass spectrometry. Mass Spectrom. Rev 2007, 26, 606– 643. 17471576
  171. [174]Cornett DS; Reyzer ML; Chaurand P; Caprioli RM MALDI imaging mass spectrometry: molecular snapshots of bio-chemical systems. Nat. Methods 2007, 4, 828– 833. 17901873
  172. [175]Powers TW; Jones EE; Betesh LR; Romano PR; Gao P; Copland JA; Mehta AS; Drake RR Matrix assisted laser desorption ionization imaging mass spectrometry workflow for spatial profiling analysis of N-linked glycan expression in tissues. Anal. Chem 2013, 85, 9799– 9806. 24050758 PMC3969840
  173. [176]Drake RR; Powers TW; Jones EE; Bruner E; Mehta AS; Angel PM MALDI Mass Spectrometry Imaging of N-Linked Glycans in Cancer Tissues. Adv. Cancer Res 2017, 134, 85– 116. 28110657 PMC6020705
  174. [177]Powers T; Holst S; Wuhrer M; Mehta A; Drake R Two-Dimensional N-Glycan Distribution Mapping of Hepatocellular Carcinoma Tissues by MALDI-Imaging Mass Spectrometry. Biomolecules 2015, 5, 2554. 26501333 PMC4693247
  175. [178]Powers TW; Neely BA; Shao Y; Tang H; Troyer DA; Mehta AS; Haab BB; Drake RR MALDI Imaging Mass Spectrometry Profiling of N-Glycans in Formalin-Fixed Paraffin Embedded Clinical Tissue Blocks and Tissue Microarrays. PLoS One 2014, 9, e106255. 25184632 PMC4153616
  176. [179]Holst S; Heijs B; de Haan N; van Zeijl RJM; Briaire-de Bruijn IH; van Pelt GW; Mehta AS; Angel PM; Mesker WE; Tollenaar RA; Linkage-Specific in Situ Sialic Acid Derivatization for N-Glycan Mass Spectrometry Imaging of Formalin-Fixed Paraffin-Embedded Tissues. Anal. Chem 2016, 88, 5904– 5913. 27145236
  177. [180]Heijs B; Holst S; Briaire-de Bruijn IH; van Pelt GW; de Ru AH; van Veelen PA; Drake RR; Mehta AS; Mesker WE; Tollenaar RA; Multimodal Mass Spectrometry Imaging of N-Glycans and Proteins from the Same Tissue Section. Anal. Chem 2016, 88, 7745– 7753. 27373711
  178. [181]Everest-Dass AV; Briggs MT; Kaur G; Oehler MK; Hoffmann P; Packer NH N-Glycan MALDI Imaging Mass Spectrometry on Formalin-Fixed Paraffin-Embedded Tissue Enables the Delineation of Ovarian Cancer Tissues. Mol. Cell. Proteomics 2016, 15, 3003– 3016. 27412689 PMC5013313
  179. [182]Nwosu C; Yau HK; Becht S Assignment of Core versus Antenna Fucosylation Types in Protein N-Glycosylation via Procainamide Labeling and Tandem Mass Spectrometry. Anal. Chem 2015, 87, 5905– 5913. 25978524
  180. [183]Zhang JH; Schubothe K; Li BS; Russell S; Lebrilla CB Infrared multiphoton dissociation of O-linked mucin-type oligosaccharides. Anal. Chem 2005, 77, 208– 214. 15623298
  181. [184]Lancaster KS; An HJ; Li BS; Lebrilla CB Interrogation of N-linked oligosaccharides using infrared multiphoton dissociation in FT-ICR mass spectrometry. Anal. Chem 2006, 78, 4990– 4997. 16841922
  182. [185]Williams JP; Pringle S; Richardson K; Gethings L; Vissers JP; De Cecco M; Houel S; Chakraborty AB; Yu YQ; Chen W; Characterisation of glycoproteins using a quadrupole time-of-flight mass spectrometer configured for electron transfer dissociation. Rapid Commun. Mass Spectrom 2013, 27, 2383– 2390. 24097394
  183. [186]Huang Y; Yu X; Mao Y; Costello CE; Zaia J; Lin C De novo sequencing of heparan sulfate oligosaccharides by electron-activated dissociation. Anal. Chem 2013, 85, 11979– 11986. 24224699 PMC3912864
  184. [187]Zhou S; Dong X; Veillon L; Huang Y; Mechref Y LC-MS/MS analysis of permethylated N-glycans facilitating isomeric characterization. Anal. Bioanal. Chem 2017, 409, 453– 466. 27796453 PMC5444817
  185. [188]Wheeler SF; Harvey DJ Negative ion mass spectrometry of sialylated carbohydrates: Discrimination of N-acetylneuraminic acid linkages by MALDI-TOF and ESI-TOF mass spectrometry. Anal. Chem 2000, 72, 5027– 5039. 11055725
  186. [189]Michael C; Rizzi AM Tandem mass spectrometry of isomeric aniline-labeled N-glycans separated on porous graphitic carbon: Revealing the attachment position of terminal sialic acids and structures of neutral glycans. Rapid Commun. Mass Spectrom 2015, 29, 1268– 1278. 26395610
  187. [190]Harvey DJ; Mattu TS; Wormald MR; Royle L; Dwek RA; Rudd PM ″Internal residue loss″: Rearrangements occurring during the fragmentation of carbohydrates derivatized at the reducing terminus. Anal. Chem 2002, 74, 734– 740. 11866052
  188. [191]Fellenberg M; Behnken HN; Nagel T; Wiegandt A; Baerenfaenger M; Meyer B Glycan analysis: scope and limitations of different techniques-a case for integrated use of LC-MS(/MS) and NMR techniques. Anal. Bioanal. Chem 2013, 405, 7291– 7305. 23852147
  189. [192]Wiegandt A; Meyer B Unambiguous characterization of N-glycans of monoclonal antibody cetuximab by integration of LC-MS/MS and (1)H NMR spectroscopy. Anal. Chem 2014, 86, 4807– 4814. 24725217
  190. [193]Smith DF; Cummings RD Application of microarrays for deciphering the structure and function of the human glycome. Mol. Cell. Proteomics 2013, 12, 902– 912. 23412570 PMC3617337
  191. [194]Guttman A Multistructure sequencing of N-linked fetuin glycans by capillary gel electrophoresis and enzyme matrix digestion. Electrophoresis 1997, 18, 1136– 1141. 9237569
  192. [195]Guttman A; Ulfelder KW Exoglycosidase matrix-mediated sequencing of a complex glycan pool by capillary electrophoresis. J. Chromatogr. A 1997, 781, 547– 554. 9368399
  193. [196]Royle L; Radcliffe CM; Dwek RA; Rudd PM Detailed structural analysis of N-glycans released from glycoproteins in SDS-PAGE gel bands using HPLC combined with exoglycosidase array digestions. Methods Mol. Biol 2006, 347, 125– 143. 17072008
  194. [197]Takegawa Y; Deguchi K; Nakagawa H; Nishimura S Structural analysis of an N-glycan with ″beta1–4 bisecting branch″ from human serum IgG by negative-ion MSn spectral matching and exoglycosidase digestion. Anal. Chem 2005, 77, 6062– 6068. 16159142
  195. [198]Campbell MP; Royle L; Radcliffe CM; Dwek RA; Rudd PM GlycoBase and autoGU: tools for HPLC-based glycan analysis. Bioinformatics 2008, 24, 1214– 1216. 18344517
  196. [199]Campbell MP; Royle L; Rudd PM GlycoBase and autoGU: resources for interpreting HPLC-glycan data. Methods Mol. Biol 2015, 1273, 17– 28. 25753700
  197. [200]Aldredge D; An HJ; Tang N; Waddell K; Lebrilla CB Annotation of a serum N-glycan library for rapid identification of structures. J. Proteome Res 2012, 11, 1958– 1968. 22320385 PMC3292799
  198. [201]Abrahams JL; Campbell MP; Packer NH Building a PGC-LC-MS N-glycan retention library and elution mapping resource. Glycoconjugate J. 2017, 9793– 4. 28905148
  199. [202]Kolarich D; Rapp E; Struwe WB; Haslam SM; Zaia J; McBride R; Agravat S; Campbell MP; Kato M; Ranzinger R; The minimum information required for a glycomics experiment (MIRAGE) project: improving the standards for reporting mass-spectrometry-based glycoanalytic data. Mol. Cell. Proteomics 2013, 12, 991– 995. 23378518 PMC3617344
  200. [203]York WS; Agravat S; Aoki-Kinoshita KF; McBride R; Campbell MP; Costello CE; Dell A; Feizi T; Haslam SM; Karlsson N; MIRAGE: the minimum information required for a glycomics experiment. Glycobiology 2014, 24, 402– 406. 24653214 PMC3976285

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Authors
Ruhaak, L. R., Xu, G., Li, Q., Goonatilleke, E., & Lebrilla, C. B.
Affiliations
  • Leiden University Medical Center (NL)
  • University of California, Davis (US)
Corresponding author
Lebrilla, Carlito B.
Venue
Chemical Reviews
Published
2018-03-19
Volume
118
Issue
17
Pages
7886-7930
ISSN
  • 0009-2665 (ISSN-L)
  • 1520-6890
OpenAlex
W2789682399
Cited by
395
References
6
Citations by year
2026: 32 · 2025: 44 · 2024: 48 · 2023: 40 · 2022: 50 · 2021: 77 · 2020: 50 · 2019: 45 · 2018: 8
FWCI
4.41
Type
journal article
Language
en
Open access
Locations
  • Chemical Reviews (publishedVersion)
  • PubMed (publishedVersion)
  • PubMed Central (acceptedVersion)
  • eScholarship (California Digital Library) (submittedVersion, cc-by)
  • Data Archiving and Networked Services (DANS) (submittedVersion)
  • Leiden Repository (Leiden University) (submittedVersion)
Funders
  • National Institute of Child Health and Human Development (R01 HD061923)
  • National Center for Complementary and Integrative Health (RO1 AT008759)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Glycosylation and Glycoproteins Research
  • Physical Sciences › Chemistry › Spectroscopy › Mass Spectrometry Techniques and Applications
  • Physical Sciences › Chemistry › Spectroscopy › Advanced Proteomics Techniques and Applications
Keywords
glycomics, glycoproteomics, glycans, oligosaccharides, glycan analysis, glycoforms, post-translational modification, glycan separation, mass spectrometry workflow, glycan characterization
MeSH terms
Glycoproteins, Glycosylation, Polysaccharides, Protein Processing, Post-Translational, Mass Spectrometry, Proteomics, Glycomics

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