Glycan analysis: Scope and limitations of different techniques - A case for integrated use of LC-MS(/MS) and NMR techniques

Analytical and Bioanalytical Chemistry

Volumn 405, Issue 23, 2013, Pages 7291-7305

  Fellenberg, Meike ^a   Behnken, Henning N ^a   Nagel, Tim ^a   Wiegandt, Alena ^a   Baerenfaenger, Melissa ^a   Meyer, Bernd ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

3D cross correlation (3DCC); Liquid chromatography (LC); Mass spectrometry (MS); N Glycans; Nuclear magnetic resonance (NMR); Porous graphitized carbon (PGC)

Indexed keywords

3D CROSS-CORRELATION; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; MS/MS FRAGMENTATION; N-GLYCANS; NUCLEAR MAGNETIC RESONANCE(NMR); POROUS GRAPHITIZED CARBONS; STRUCTURAL CHARACTERIZATION; TIGHT INTEGRATIONS;

LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RNA; THREE DIMENSIONAL;

POLYSACCHARIDES;

BOVINAE;

FIBRINOGEN; POLYSACCHARIDE;

ANIMAL; ARTICLE; CARBOHYDRATE ANALYSIS; CATTLE; CHEMISTRY; GLYCOSYLATION; LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY;

ANIMALS; CARBOHYDRATE SEQUENCE; CATTLE; CHROMATOGRAPHY, LIQUID; FIBRINOGEN; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; POLYSACCHARIDES; TANDEM MASS SPECTROMETRY;

EID: 84883556118     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-013-7164-y     Document Type: Article

References (43)

1. Laine RA (1994) Invited commentary: a calculation of all possible oligosaccharide isomers both branched and linear yields 1.05 × 1012 structures for a reducing hexasaccharide: the isomer barrier to development of single-method saccharide sequencing or synthesis systems. Glycobiology 4(6):759-767
2. Apweiler R, Hermjakob H, Sharon N (1999) On the frequency of protein glycosylation, as deduced from analysis of the SWISS-PROT database. Biochim Biophys Acta 1473(1):4-12
3. Dell A, Morris HR (2001) Glycoprotein structure determination mass spectrometry. Science 291(5512):2351-2356
4. Fellenberg M, Coksezen A, Meyer B (2010) Characterization of picomole amounts of oligosaccharides from glycoproteins by 1H NMR spectroscopy. Angew Chem Int Ed Engl 49(14):2630-2633
5. Wilhelm D, Behnken HN, Meyer B (2012) Glycosylation assists binding of HIV protein gp120 to human CD4 receptor. ChemBioChem 13(4):524-527
6. Coutinho PM, Deleury E, Davies GJ, Henrissat B (2003) An evolving hierarchical family classification for glycosyltransferases. J Mol Biol 328(2):307-317
7. Kikuchi N, Narimatsu H (2006) Bioinformatics for comprehensive finding and analysis of glycosyltransferases. Biochim Biophys Acta, Gen Subj 1760(4):578-583
8. Pabst M, Bondili JS, Stadlmann J, Mach L, Altmann F (2007) Mass plus retention time = structure: a strategy for the analysis of N-glycans by carbon LC-ESI-MS and its application to fibrin N-glycans. Anal Chem 79(13):5051-5057
9. Ruhaak LR, Deelder AM, Wuhrer M (2009) Oligosaccharide analysis by graphitized carbon liquid chromatography-mass spectrometry. Anal Bioanal Chem 394(1):163-174
10. Wuhrer M, Deelder AM (2005) Negative-mode MALDI-TOF/TOF-MS of oligosaccharides labeled with 2-aminobenzamide. Anal Chem 77(21):6954-6959
11. König S, Leary J (1998) Evidence for linkage position determination in cobalt coordinated pentasaccharides using ion trap mass spectrometry. J Am Soc Mass Spectrom 9(11):1125-1159
12. Viseux N, de Hoffmann E, Domon B (1998) Structural assignment of permethylated oligosaccharide subunits using sequential tandem mass spectrometry. Anal Chem 70(23):4951-4960
13. Weiskopf A, Vouros P, Harvey D (1998) Electrospray ionization-ion trap mass spectrometry for structural analysis of complex N-linked glycoprotein oligosaccharides. Anal Chem 70(20):4441-4448
14. Domon B, Costello CE (1988) A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates. Glycoconjugate J 5(4):397-409
15. Harvey DJ (2005) Structural determination of N-linked glycans by matrix-assisted laser desorption/ionization and electrospray ionization mass spectrometry. Proteomics 5(7):1774-1786
16. van Kuik JA, Vliegenthart JFG (1992) Databases of complex carbohydrates. Trends Biotechnol 10(6):182-185
17. van Kuik JA, Hard K, Vliegenthart JFG (1992) A H-1-NMR database computer-program for the analysis of the primary structure of complex carbohydrates. Carbohydr Res 235:53-68
18. Meyer B, Hansen T, Nute D, Albersheim P, Darvill A, York W, Sellers J (1991) Identification of the H-1-NMR spectra of complex oligosaccharides with artificial neural networks. Science 251(4993):542-544
19. Vliegenthart JFG, Dorland L, van Halbeek H (1983) High-resolution, H-1-nuclear magnetic-resonance spectroscopy as a tool in the structural-analysis of carbohydrates related to glycoproteins. Adv Carbohydr Chem Biochem 41:209-374
20. Harvey DJ (2001) Identification of protein-bound carbohydrates by mass spectrometry. Proteomics 1(2):311-328
21. Leeflang BR, Vliegenthart JFG (2006) Glycoprotein analysis: using nuclear magnetic resonance. In: Meyers R (ed) Encyclopedia of analytical chemistry. Wiley, New York
22. Behnken HN, Fellenberg M, Koetzler MP, Jirmann R, Nagel T, Meyer B (2012) Resolving the problem of chromatographic overlap by 3D cross correlation (3DCC) processing of LC, MS and NMR data for characterization of complex glycan mixtures. Anal Bioanal Chem 404(5):1427-1437
23. Tamura T, Wadhwa MS, Rice KG (1994) Reducing-end modification of N-linked oligosaccharides with tyrosine. Anal Biochem 216(2):335-344
24. Rice KG, DaSilva MLC (1996) Preparative purification of tyrosinamide N-linked oligosaccharides. J Chromatogr A 720(1-2):235-249
25. Kötzler M, Blank S, Behnken H, Alpers D, Bantleon F, Spillner E, Meyer B (2012) Formation of the immunogenic α1,3-fucose epitope: elucidation of substrate specificity and of enzyme mechanism of core fucosyltransferase A. Insect Biochem Mol Biol 42(2):116-141
26. Ceroni A, Maass K, Geyer H, Geyer R, Dell A, Haslam S (2008) GlycoWorkbench: a tool for the computer-assisted annotation of mass spectra of glycans. J Proteome Res 7(4):1650-1659
27. Wishart DS, Bigam CG, Holm A, Hodges RS, Sykes BD (1995) H-1, C-13 and N-15 random coil NMR chemical-shifts of the common amino-acids. 1. Investigations of nearest-neighbor effects. J Biomol NMR 5(1):67-81
28. Fan JQ, Kondo A, Kato I, Lee YC (1994) High-performance liquid chromatography of glycopeptides and oligosaccharides on graphitized carbon columns. Anal Biochem 219(2):224-229
29. Lewandrowski U, Resemann A, Sickmann A (2005) Laser-induced dissociation/high-energy collision-induced dissociation fragmentation using MALDI-TOF/TOF-MS instrumentation for the analysis of neutral and acidic oligosaccharides. Anal Chem 77(10):3274-3357
30. Stephens E, Maslen S, Green L, Williams D (2004) Fragmentation characteristics of neutral N-linked glycans using a MALDI-TOF/TOF tandem mass spectrometer. Anal Chem 76(8):2343-2354
31. Bendiak B, Orr J, Brockhausen I, Vella G, Phoebe C (1988) Separation of neutral reducing oligosaccharides derived from glycoproteins by HPLC on a hydroxylated polymeric support. Anal Biochem 175(1):96-201
32. Bernard N, Engler R, Strecker G, Montreuil J, van Halbeek H, Vliegenthart JFG (1984) The structure of a trisialyl di-antennary N-type glycopeptide obtained from rat plasma hemopexin. Glycoconjugate J 1(2):123-140
33. Bergwerff A, Stroop C, Murray B, Holtorf A, Pluschke G, Van Oostrum J, Kamerling J, Vliegenthart J (1995) Variation in N-linked carbohydrate chains in different batches of two chimeric monoclonal IgG1 antibodies produced by different murine SP2/0 transfectoma cell subclones. Glycoconjugate J 12(3):318-348
34. de Waard P, Koorevaar A, Kamerling JP, Vliegenthart JF (1991) Structure determination by 1H NMR spectroscopy of (sulfated) sialylated N-linked carbohydrate chains released from porcine thyroglobulin by peptide-N4-(N-acetyl- beta-glucosaminyl)asparagine amidase-F. J Biol Chem 266(7):4237-4243
35. Hokke C, Bergwerff A, Van Dedem G, Kamerling J, Vliegenthart J (1995) Structural analysis of the sialylated N- and O-linked carbohydrate chains of recombinant human erythropoietin expressed in Chinese hamster ovary cells. Sialylation patterns and branch location of dimeric N-acetyllactosamine units. Eur J Biochem 228(3):981-1008
36. Lipniunas P, Grönberg G, Krotkiewski H, Angel A, Nilsson B (1993) Investigation of the structural heterogeneity in the carbohydrate portion of a mouse monoclonal immunoglobulin A antibody. Arch Biochem Biophys 300(1):335-345
37. Zaia J (2004) Mass spectrometry of oligosaccharides. Mass Spectrom Rev 23(3):161-227
38. 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(19):7534-7542
39. Manger I, Rademacher T, Dwek R (1992) 1-N-Glycyl beta-oligosaccharide derivatives as stable intermediates for the formation of glycoconjugate probes. Biochemistry-Us 31(44):10724-10732
40. Pabst M, Kolarich D, Pöltl G, Dalik T, Lubec G, Hofinger A, Altmann F (2009) Comparison of fluorescent labels for oligosaccharides and introduction of a new postlabeling purification method. Anal Biochem 384(2):263-273
41. Harvey DJ (2005) Collision-induced fragmentation of negative ions from N-linked glycans derivatized with 2-aminobenzoic acid. J Mass Spectrom 40(5):642-653
42. Harvey DJ, Sobott F, Crispin M, Wrobel A, Bonomelli C, Vasiljevic S, Scanlan CN, Scarff CA, Thalassinos K, Scrivens JH (2011) Ion mobility mass spectrometry for extracting spectra of N-glycans directly from incubation mixtures following glycan release: application to glycans from engineered glycoforms of intact, folded HIV gp120. J Am Soc Mass Spectrom 22(3):568-581
43. Leymarie N, Zaia J (2012) Effective use of mass spectrometry for glycan and glycopeptide structural analysis. Anal Chem 84(7):3040-3048