Nanoscale reversed-phase liquid chromatography-mass spectrometry of permethylated N-glycans

Analytical and Bioanalytical Chemistry

Volumn 405, Issue 8, 2013, Pages 2469-2480

  Ritamo, Ilja ^a   Räbinä, Jarkko ^a   Natunen, Suvi ^a   Valmu, Leena ^a,b  

^a FINNISH RED CROSS BLOOD SERVICE   (Finland)

^b Biova Ltd   (Finland)

Author keywords

Glycan; Liquid chromatography; Mass spectrometry; Permethylation

Indexed keywords

ALPHA-1-ACID GLYCOPROTEIN; CHROMATOGRAPHIC RESOLUTIONS; ELECTROSPRAY TANDEM MASS SPECTROMETRY; GLYCAN; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; PERMETHYLATION; REVERSED-PHASE CHROMATOGRAPHY; REVERSED-PHASE LIQUID CHROMATOGRAPHY;

LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHYLATION; NANOTECHNOLOGY; SEPARATION;

POLYSACCHARIDES;

IMMUNOGLOBULIN G; OROSOMUCOID; POLYSACCHARIDE;

ARTICLE; CHEMISTRY; EVALUATION; HUMAN; ISOLATION AND PURIFICATION; ISOMERISM; MASS SPECTROMETRY; METHODOLOGY; METHYLATION; REVERSED PHASE LIQUID CHROMATOGRAPHY;

CHROMATOGRAPHY, REVERSE-PHASE; HUMANS; IMMUNOGLOBULIN G; ISOMERISM; MASS SPECTROMETRY; METHYLATION; OROSOMUCOID; POLYSACCHARIDES;

EID: 84878387687     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-012-6680-5     Document Type: Article

References (74)

1. Marth JD, Grewal PK (2008) Mammalian glycosylation in immunity. Nat Rev Immunol 8:874-887
2. van Kooyk Y, Rabinovich GA (2008) Protein-glycan interactions in the control of innate and adaptive immune responses. Nat Immunol 9:593-601
3. Kim Y, Varki A (1997) Perspectives on the significance of altered glycosylation of glycoproteins in cancer. Glycoconjugate J 14:569-576
4. Fuster MM, Esko JD (2005) The sweet and sour of cancer: glycans as novel therapeutic targets. Nat Rev Cancer 5:526-542
5. Pang PC, Chiu PC, Lee CL, Chang LY, Panico M, Morris HR, Haslam SM, Khoo KH, Clark GF, Yeung WS, Dell A (2011) Human sperm binding is mediated by the sialyl-Lewis(x) oligosaccharide on the zona pellucida. Science 333:1761-1764
6. Dennis JW, Granovsky M, Warren CE (1999) Protein glycosylation in development and disease. Bioessays 21:412-421
7. Haltiwanger RS, Lowe JB (2004) Role of glycosylation in development. Annu Rev Biochem 73:491-537
8. Karas M, Bachmann D, Bahr U, Hillenkamp F (1987) Matrix-assisted ultraviolet laser desorption of non-volatile compounds. Int J Mass Spectrom Ion Process 78:53-68
9. Mittermayr S, Bones J, Doherty M, Guttman A, Rudd PM (2011) Multiplexed analytical glycomics: rapid and confident IgG N-glycan structural elucidation. J Proteome Res 10:3820-3829
10. Rudd PM, Dwek RA (1997) Rapid, sensitive sequencing of oligosaccharides from glycoproteins. Curr Opin Biotechnol 8:488-497
11. Royle L, Dwek RA, Rudd PM (2001) Current protocols in protein science. Wiley, New York
12. Whitehouse CM, Dreyer RN, Yamashita M, Fenn JB (1985) Electrospray interface for liquid chromatographs and mass spectrometers. Anal Chem 57:675-679
13. Harvey DJ (2005) Structural determination of N-linked glycans by matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometry. Proteomics 5:1774-1786
14. Harvey DJ (1993) Quantitative aspects of the matrix-assisted laser desorption mass spectrometry of complex oligosaccharides. Rapid Commun Mass Spectrom 7:614-619
15. Bentley R, Sweeley CC, Makita M, Wells WW (1963) Gas chromatography of sugars and other polyhydroxy compounds. Biochem Biophys Res Commun 11:14-18
16. Honda S, Makino A, Suzuki S, Kakehi K (1990) Analysis of the oligosaccharides in ovalbumin by high-performance capillary electrophoresis. Anal Biochem 191:228-234
17. Alpert AJ (1990) Hydrophilic-interaction chromatography for the separation of peptides, nucleic acids and other polar compounds. J Chromatogr A 499:177-196
18. Reich WS (1939) A method for the separation of sugars by the chromatographic adsorption of their coloured esters: separation of glucose and fructose. Biochem J 33:1000-1004
19. Davies M, Smith KD, Harbin A, Hounsell EF (1992) High-performance liquid chromatography of oligosaccharide alditols and glycopeptides on a graphitized carbon column. J Chromatogr A 609:125-131
20. Jolley RL, Warren KS, Scott CD, Jainchill JL, Freeman ML (1970) Carbohydrates in normal urine and blood serum as determined by high-resolution column chromatography. Am J Clin Pathol 53:793-802
21. Townsend RR, Hardy MR (1991) Analysis of glycoprotein oligosaccharides using high-pH anion exchange chromatography. Glycobiology 1:139-147
22. Tolstikov VV, Fiehn O (2002) Analysis of highly polar compounds of plant origin: combination of hydrophilic interaction chromatography and electrospray ion trap mass spectrometry. Anal Biochem 301:298-307
23. Bruggink C, Wuhrer M, Koeleman CAM, Barreto V, Liu Y, Pohl C, Ingendoh A, Hokke CH, Deelder AM (2005) Oligosaccharide analysis by capillary-scale high-pH anion-exchange chromatography with on-line ion-trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 829:136-143
24. Niñonuevo M, An H, Yin H, Killeen K, Grimm R, Ward R, German B, Lebrilla C (2005) Nanoliquid chromatography-mass spectrometry of oligosaccharides employing graphitized carbon chromatography on microchip with a high-accuracy mass analyzer. Electrophoresis 26:3641-3649
25. Ruhaak L, Deelder A, Wuhrer M (2009) Oligosaccharide analysis by graphitized carbon liquid chromatography-mass spectrometry. Anal Bioanal Chem 394:163-174
26. Wuhrer M, Koeleman CAM, Deelder AM (2009) In: Walker JM (ed) Methods in molecular biology. Humana Press Inc, New York
27. Hua S, Nwosu C, Strum J, Seipert R, An H, Zivkovic A, German J, Lebrilla C (2012) Site-specific protein glycosylation analysis with glycan isomer differentiation. Anal Bioanal Chem 403:1291-1302
28. Karlsson NG, McGuckin MA (2012) O-linked glycome and proteome of high molecular mass proteins in human ovarian cancer ascites: identification of sulfation, disialic acid and O-linked fucose. Glycobiology 22:918-929
29. Ceroni A, Maass K, Geyer H, Geyer R, Dell A, Haslam SM (2008) GlycoWorkbench: a tool for the computer-assisted annotation of mass spectra of glycans. J Proteome Res 7:1650-1659
30. 2 profiling of N-glycans. Glycoconj J. doi: 10.1007/s10719-012-9412-3
31. Hakomori S (1964) A rapid permethylation of glycolipid, and polysaccharide catalyzed by methylsulfinyl carbanion in dimethyl sulfoxide. J Biochem 55:205-208
32. Kang P, Mechref Y, Klouckova I, Novotny MV (2005) Solid-phase permethylation of glycans for mass spectrometric analysis. Rapid Commun Mass Spectrom 19:3421-3428
33. Alvarez-Manilla G, Warren NL, Abney T, Atwood J, Azadi P, York WS, Pierce M, Orlando R (2007) Tools for glycomics: relative quantitation of glycans by isotopic permethylation using 13CH3I. Glycobiology 17:677-687
34. Delaney J, Vouros P (2001) Liquid chromatography ion trap mass spectrometric analysis of oligosaccharides using permethylated derivatives. Rapid Commun Mass Spectrom 15:325-334
35. Hanisch F, Müller S (2009) Analysis of methylated O-glycan alditols by reversed-phase NanoLC coupled CAD-ESI mass spectrometry. Methods Mol Biol 534:107-115
36. Alley WR, Madera M, Mechref Y, Novotny MV (2010) Chip-based reversed-phase liquid chromatography-mass spectrometry of permethylated N-linked glycans: a potential methodology for cancer-biomarker discovery. Anal Chem 82:5095-5106
37. Kinter M, Sherman NE (2005) Protein sequencing and identification using tandem mass spectrometry, 1st edn. Wiley, Hoboken
38. Nuck R, Zimmermann M, Sauvageot D, Josi D, Reutter W (1990) Optimized deglycosylation of glycoproteins by peptide-N4-(N-acetyl-beta-glucosaminyl)- asparagine amidase from Flavobacterium meningosepticum. Glycoconj J 7:279-286
39. Jang-Lee J, North SJ, Sutton-Smith M, Goldberg D, Panico M, Morris H, Haslam S, Dell A (2006) Glycomic profiling of cells and tissues by mass spectrometry: fingerprinting and sequencing methodologies. Methods Enzymol 415:59-86
40. Itoh S, Kawasaki N, Ohta M, Hyuga M, Hyuga S, Hayakawa T (2002) Simultaneous microanalysis of N-linked oligosaccharides in a glycoprotein using microbore graphitized carbon column liquid chromatography-mass spectrometry. J Chromatogr A 968:89-100
41. Packer NH, Lawson MA, Jardine DR, Redmond JW (1998) A general approach to desalting oligosaccharides released from glycoproteins. Glycoconj J 15:737-747
42. Kang P, Mechref Y, Novotny MV (2008) High-throughput solid-phase permethylation of glycans prior to mass spectrometry. Rapid Commun Mass Spectrom 22:721-734
43. Wuhrer M, Deelder AM, van der Burgt YEM (2011) Mass spectrometric glycan rearrangements. Mass Spectrom Rev 30:664-680
44. Pabst M, Altmann F (2008) Influence of electrosorption, solvent, temperature, and ion polarity on the performance of LC-ESI-MS using graphitic carbon for acidic oligosaccharides. Anal Chem 80:7534-7542
45. Kamiyama F, Yamazaki K, Kawamura K, Kohara M (1996) Temperature dependence of retention in reversed-phase liquid chromatography on a porous acrylic support. Biomed Chromatogr 10:105-110
46. Doyle CA, Vickers TJ, Mann CK, Dorsey JG (2000) Characterization of C18-bonded liquid chromatographic stationary phases by Raman spectroscopy: the effect of temperature. J Chromatogr A 877:41-59
47. Costello C, Contado-Miller J, Cipollo J (2007) A glycomics platform for the analysis of permethylated oligosaccharide alditols. J Am Soc Mass Spectrom 18:1799-1812
48. Durandy A, Kaveri SV, Kuijpers TW, Basta M, Miescher S, Ravetch JV, Rieben R (2009) Intravenous immunoglobulins - understanding properties and mechanisms. Clin Exp Immunol 158(Suppl 1):2-13
49. Rezaei N, Abolhassani H, Aghamohammadi A, Ochs HD (2011) Indications and safety of intravenous and subcutaneous immunoglobulin therapy. Expert Rev Clin Immunol 7:301-316
50. Hodoniczky J, Zheng YZ, James DC (2005) Control of recombinant monoclonal antibody effector functions by Fc N-glycan remodeling in vitro. Biotechnol Prog 21:1644-1652
51. Iida S, Kuni-Kamochi R, Mori K, Misaka H, Inoue M, Okazaki A, Shitara K, Satoh M (2009) Two mechanisms of the enhanced antibody-dependent cellular cytotoxicity (ADCC) efficacy of non-fucosylated therapeutic antibodies in human blood. BMC Cancer 9:58
52. Kaneko Y, Nimmerjahn F, Ravetch JV (2006) Anti-inflammatory activity of immunoglobulin G resulting from Fc sialylation. Science 313:670-673
53. Parekh RB, Dwek RA, Sutton BJ, Fernandes DL, Leung A, Stanworth D, Rademacher TW, Mizuochi T, Taniguchi T, Matsuta K (1985) Association of rheumatoid arthritis and primary osteoarthritis with changes in the glycosylation pattern of total serum IgG. Nature 316:452-457
54. Scherer HU, Burmester GR (2009) A clinical perspective of rheumatoid arthritis. Eur J Immunol 39:2044-2048
55. Scherer HU, van der Woude D, Ioan-Facsinay A, el Bannoudi H, Trouw LA, Wang J, Haupl T, Burmester GR, Deelder AM, Huizinga TW, Wuhrer M, Toes RE (2010) Glycan profiling of anti-citrullinated protein antibodies isolated from human serum and synovial fluid. Arthritis Rheum 62:1620-1629
56. Wuhrer M, Porcelijn L, Kapur R, Koeleman CA, Deelder A, de Haas M, Vidarsson G (2009) Regulated glycosylation patterns of IgG during alloimmune responses against human platelet antigens. J Proteome Res 8:450-456
57. Selman MHJ, Derks RJE, Bondt A, Palmblad M, Schoenmaker B, Koeleman CAM, van de Geijn FE, Dolhain RJEM, Deelder AM, Wuhrer M (2012) Fc specific IgG glycosylation profiling by robust nano-reverse phase HPLC-MS using a sheath-flow ESI sprayer interface. J Proteomics 75:1318-1329
58. Wang J, Balog CI, Stavenhagen K, Koeleman CA, Scherer HU, Selman MH, Deelder AM, Huizinga TW, Toes RE, Wuhrer M (2011) Fc-glycosylation of IgG1 is modulated by B-cell stimuli. Mol Cell Proteomics 10:M110.004655
59. Walsh G (2010) Biopharmaceutical benchmarks 2010. Nat Biotechnol 28:917-924
60. Stadlmann J, Weber A, Pabst M, Anderle H, Kunert R, Ehrlich HJ, Peter Schwarz H, Altmann F (2009) A close look at human IgG sialylation and subclass distribution after lectin fractionation. Proteomics 9:4143-4153
61. Stadlmann J, Pabst M, Kolarich D, Kunert R, Altmann F (2008) Analysis of immunoglobulin glycosylation by LC-ESI-MS of glycopeptides and oligosaccharides. Proteomics 8:2858-2871
62. Huhn C, Selman MH, Ruhaak LR, Deelder AM, Wuhrer M (2009) IgG glycosylation analysis. Proteomics 9:882-913
63. Turner GA (1992) N-glycosylation of serum proteins in disease and its investigation using lectins. Clin Chim Acta 208:149-171
64. van Dijk W, Havenaar EC, Brinkman-van der Linden EC (1995) Alpha 1-acid glycoprotein (orosomucoid): pathophysiological changes in glycosylation in relation to its function. Glycoconj J 12:227-233
65. Gornik O, Lauc G (2008) Glycosylation of serum proteins in inflammatory diseases. Dis Markers 25:267-278
66. Fournier T, Medjoubi-N N, Porquet D (2000) Alpha-1-acid glycoprotein. Biochim Biophys Acta 1482:157-171
67. Hochepied T, Berger FG, Baumann H, Libert C (2003) Alpha(1)-acid glycoprotein: an acute phase protein with inflammatory and immunomodulating properties. Cytokine Growth Factor Rev 14:25-34
68. de Vries B, Walter SJ, Wolfs TG, Hochepied T, Räbinä J, Heeringa P, Parkkinen J, Libert C, Buurman WA (2004) Exogenous alpha-1-acid glycoprotein protects against renal ischemia-reperfusion injury by inhibition of inflammation and apoptosis. Transplantation 78:1116-1124
69. Israili ZH, Dayton PG (2001) Human alpha-1-glycoprotein and its interactions with drugs. Drug Metab Rev 33:161-235
70. Arnold JN, Wormald MR, Sim RB, Rudd PM, Dwek RA (2007) The impact of glycosylation on the biological function and structure of human immunoglobulins. Annu Rev Immunol 25:21-50
71. Wada Y, Azadi P, Costello CE, Dell A, Dwek RA, Geyer H, Geyer R, Kakehi K, Karlsson NG, Kato K, Kawasaki N, Khoo K, Kim S, Kondo A, Lattova E, Mechref Y, Miyoshi E, Nakamura K, Narimatsu H, Novotny MV, Packer NH, Perreault H, Peter-Katalinić J, Pohlentz G, Reinhold VN, Rudd PM, Suzuki A, Taniguchi N (2007) Comparison of the methods for profiling glycoprotein glycans - HUPO Human Disease Glycomics/Proteome Initiative multi-institutional study. Glycobiology 17:411-422
72. Wuhrer M, Stam JC, van de Geijn FE, Koeleman CAM, Verrips CT, Dolhain RJEM, Hokke CH, Deelder AM (2007) Glycosylation profiling of immunoglobulin G (IgG) subclasses from human serum. Proteomics 7:4070-4081
73. Imre T, Schlosser G, Pocsfalvi G, Siciliano R, Molnár- Szöllosi É, Kremmer T, Malorni A, Vékey K (2005) Glycosylation site analysis of human alpha-1-acid glycoprotein (AGP) by capillary liquid chromatography-electrospray mass spectrometry. J Mass Spectrom 40:1472-1483
74. Domon B, Costello CE (1988) A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconj J 5:397-409