Monosaccharide compositional analysis of glycoproteins using liquid chromatography-mass spectrometry

Current Proteomics

Volumn 8, Issue 4, 2011, Pages 257-268

  Hammad, Loubna A ^a   Mechref, Yehia ^b  

^a INDIANA UNIVERSITY   (United States)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

Glycans; High performance liquid chromatography; LC MS; Monosaccharides

Indexed keywords

GLYCOCONJUGATE; GLYCOLIPID; GLYCOPROTEIN; MONOSACCHARIDE;

ACCURACY; ANALYTIC METHOD; CAPILLARY ELECTROPHORESIS; CARBOHYDRATE ANALYSIS; DERIVATIZATION; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; IONIZATION; MASS SPECTROMETRY; PRIORITY JOURNAL; REVIEW; SEPARATION TECHNIQUE;

EID: 82155171411     PISSN: 15701646     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016411798220835     Document Type: Review

References (68)

1. Varki, A. Biological roles of oligosaccharides: All of the theories are correct. Glycobiology, 1993, 3, 97-130.
2. Bayliss, M.T.; Osborne, D.; Woodhouse, S. and Davidson, C. Sulfation of chondroitin sulfate in human articular cartilage: The effect of age, topographical position, and zone of cartilage on tissue composition. J. Biol. Chem., 1999, 274, 15892-15900.
3. Plaas, A.H.; West, L.A.; Wong-Palms, S. and Nelson, F.R. Glycosaminoglycan Sulfation in Human Osteoarthritis. Disease- related alterations at the non-reducing termini of chondroitin and dermatan sulfate. J. Biol. Chem., 1998, 273, 12642-12649.
4. Tondorov, P.T.; Deacon, M. and Tisdale, M.J. Structural analysis of a tumor-produced sulfated glycoprotein capable of initiating muscle protein degradation. J. Biol. Chem., 1997, 272, 12279-12288.
5. Chace, K.V.; Flux, M. and Sachdev, G.P. Comparison of physicochemical properties of purified mucus glycoproteins isolated from respiratory secretions of cystic fibrosis and asthmatic patients. Biochemistry, 1985, 24, 7334-7341.
6. Chace, K.V.; Leahy, D.S.; Martin, R.; Carubelli, R.; Flux, M. and Sachdev, G.P. Respiratory mucous secretions in patients with cystic fibrosis: relationship between levels of highly sulfated mucin component and severity of the disease. Clin. Chim. Acta, 1983, 132, 143-155.
7. Davril, M.; Degroote, S.; Humbert, P.; Galabert, C.; Dumur, V.; Lafitte, J.J.; Lamblin, G. and Roussel, P. The sialylation of bronchial mucins secreted by patients suffering from cystic fibrosis or from chronic bronchitis is related to the severity of airway infection. Glycobiology, 1999, 9, 311-321
8. Xia, B.; Royall, J.A.; Damera, G.; Sachdev, G.P. and Cummings, R.D. Altered O-glycosylation and sulfation of airway mucins associated with cystic fibrosis. Glycobiology, 2005, 15, 747-775.
9. Bowman, K.G.; Cook, B.N.; de Graffenried, C.L. and Bertozzi, C.R. Biosynthesis of L-selectin ligands: sulfation of sialyl lewis x-related oligosaccharides by a family of GlcNAc-6-sulfotransferases. Biochemistry, 2001, 40, 5382-5391.
10. Sangadala, S.; Bhat, U.R. and Mendicino, J. Structures of sulfated oligosaccharides in human trachea mucin glycoproteins Mol. Cell. Biochem., 1993, 126, 37-47.
11. Thomsson, K.A.; Karlsson, N.G. and Hansson, G.C. Liquid chromatography-electrospray mass spectrometry as a tool for the analysis of sulfated oligosaccharides from mucin glycoproteins. J. Chromatogr. A., 1999, 854, 131-139.
12. Baldus, S.E.; Wienand, J.R.; Werner, J.P.; Landsberg, S.; Drebber, U.; Hanisch, F.G. and Dienes, H.P. Expression of MUC1, MUC2 and oligosaccharide epitopes in breast cancer: prognostic significance of a sialylated MUC1 epitope. Int. J. Oncol., 2005, 27, 1289-1297.
13. Dwek, M.V.; Lacey, H.A. and Leathem, A. Breast cancer progression is associated with a reduction in the diversity of sialylated and neutral oligosaccharides. J. Clin. Chim. Acta, 1998, 271, 191-202.
14. Handerson, T.; Camp, R.; Harigopal, M.; Rimm, D. and Pawelek, J. Beta 1,6-branched oligosaccharides are increased in lymph node metastases and predict poor outcome in breast carcinoma. Clin. Cancer Res., 2005, 11, 2969-2973.
15. Alper, J.; Glycobiology. Turning sweet on cancer. Science, 2003, 301, 159-160.
16. Hakomori, S. Tumor malignancy defined by aberrant glycosylation and sphingo(glyco)-lipid metabolism. Cancer Res., 1996, 56, 5309-5318.
17. Kobata, A. A retrospective and prospective view of glycopathology. Glycoconj. J., 1998, 15, 323-331.
18. Manzi, A.E. and H.v. Halbeek, Principles of Structural Analysis and Sequencing of Glycans, in Essentials of Glycobiology, A.V.et. al., Editor. 1999, Cold Spring Harbor Laboratory Press: Cold Spring Harbor. p. 581-599.
19. Binder, H. Separation of monosaccharides by high-performance liquid chromatography: comparison of ultraviolet and refractive index detection. J. Chromatogr., 1980, 189, 414-420.
20. Brons, C. and Olieman, C. Study of the high-performance liquid chromatographic separation of reducing sugars, applied to the determination of lactose sugars. J. Chromatogr., 1983, 259, 79-86.
21. Hase, S, Ikenaka, T. and Matsushima, Y. A highly sensitive method for analyses of sugar moieties of glycoproteins by fluorescence labeling. J. Biochem., 1981, 90, 407-414.
22. Anumula, K.P. Quantitative determination of monosaccharides in glycoproteins by high-performance liquid chromatography with highly sensitive fluorescence detection. Anal. Biochem., 1994, 275, 275.
23. Bigge, J.C.; Patel, T.P.; Bruce, J.A. Gouling, P.N.; Charles, S.M. and Parekh, R.B. Nonselective and efficient fluorescent lableing of glycans using 2-amino benzamide and anthranilic acid. Anal. Biochem., 1995, 230, 229-238.
24. Hara, S.; Takemori, Y.; Yamaguchi, M.; Nakamura, M. and Ohkura, Y. Fluorometric high-performance liquid chromatgraphy of N-acetyl- and N-glycolylneuraminic acids and its application on their microdetermination in human and animal sera, glycoproteins, and glycolipids. Anal. Biochem., 1987, 164, 138-145.
25. Hardy, M.R.; Townsend, R.R. and Lee, Y.C. Monosaccharide analysis of glycoconjugates by anion exchange chromatography with pulsed amperometric detection. Anal. Biochem., 1988, 170, 54-62.
26. Conboy, J.J. and Henion, J.D. High-performance anion-exchange chromatography coupled with mass spectrometry for the determination of carbohydrates. Biol. Mass Spectrom., 1992, 21, 397-407.
27. Conboy, J.J.; Henion, J.D.; Martin, M.W. and Zweigenbaum, J.A. Ion chromatography/mass spectrometry for the determination of organic ammonium and sulfate compounds. Anal. Chem., 1990, 62, 800-807.
28. Simpson, R.C.; Fenselau, C.C.; Hardy, M.R.; Townsend, R.R.; Lee, Y.C. and Cotter, R.J. Adaptation of a thermospray liquid chromatography/mass spectrometry interface for use with alkaline anion exchange liquid chromatography of carbohydrates. Anal. Chem., 1990, 62, 248-252.
29. Cataldi, T.R.I.; Campa, C. and De Benedetto, G.E. Carbohydrate analysis by high-performance anion-exchange chromatography with pulsed amperometric detection: The potential is still growing. Fresenius J. Anal. Chem., 2000, 368, 739-758.
30. Lee, Y.C.; Carbohydrate analyses with high-performance anion-exchange chromatography. J. Chromatogr. A., 1996, 720, 137-149.
31. Spellman, M.W.; Carbohydrate characterization of recombinant glycoproteins of pharmaceutical interest. Anal. Chem., 1990, 62, 1714-1722.
32. Huck, C.W.; Huber, C.G. and Bonn, G.K. HPLC of carbohydrate with cation- and anion-exchange silica and resin-based stationary phases, in Carbohydrate analysis by modern chromatgraphy and electrophoresis. Z. El Rassi, Editor. 2002, Elsevier Science B.V.: Amsterdam, The Netherlands. 182-201.
33. Liu J.; Shirota, O. Wiesler D. and Novotny M.V. Ultrasensitive fluorometric detection of carbohydrates as derivatives in mixtures separated by capillary electrophoresis. Proc. Natl. Acad. Sci. USA, 1991, 88, 2302-2306.
34. Evangelista, R.A.; Liu, M.S. and Chen, F.-T. Characterization of 9-aminopyrene-1,4,6-trisulfonate derivatized sugars by capillary electrophoresis with laser-induced fluorescence detection. An. Chem., 1995, 67, 2239-2245.
35. Chen, F.-T. and Evangelista, R.A. Analysis of mono- and oligosaccahride isomers derivatized with 9-aminopyrene-1,4,6- trisulfonate by capillary electrophoresis with laser-induced fluorescence. Anal. Biochem., 1995, 230, 273-280.
36. Liu, J.P.; Osamu, O. and Novotny, M.V. Capillary Electrophoresis of Amino Sugars With Laser-Induced Fluorescence Detection. Anal. Chem., 1991, 63, 413-417.
37. Zhang, Y.; Arriaga, E.; Diedrich, P.; Hindsgaul, O. and Dovichi, N.J. Nanomolar determination of aminated sugars by capillary electrophoresis. J. Chromatogr. A., 1995, 716, 221-229.
38. Lamari, F.N.; Kuhn, R. and Karamanos, N.K. Derivatization of carbohydrates for chromatographic, electrophoetic and mass spectrometric structure analysis. J. Chromatogr. B., 2003, 793, 15-36.
39. Townsend, R.R.; Quantitative Monosaccharide Analysis of Glycoproteins, in Chromatgraphy in Biotechnology, Horvath C. and Ettre, L.S. Editors. 1993, American Chemical Aociety: Washington, DC. p. 86-101.
40. Anumula, K. and Taylor, P.B. Quantitative determination of phenyl isothiocyanate-derivatized amino sugars and amino sugar alcohols by high-performance liquid chromatgraphy. Anal. Biochem., 1991, 197, 113-120.
41. Takeuchi, M.; Takasaki, S. Inoue N. and Kobata A. Sensitive methods for carbohydrate composition analysis of glycoproteins by high-performance liquid chromatgraphy. J. Chromatogr., 1987, 400, 207-213.
42. Eggert, F.M. and Jones, M.J. Measurement of neutral sugars in glycoproteins as dansyl derivatives by automated high-performance liquid chromatography. J. Chromatogr., 1985, 333, 123-131.
43. Varki, A. and Diaz, S. The release and purification of sialic acids from glycoconjugates: Methods to minimize the loss and migration of O-acetyl groups. Anal. Biochem., 1984, 137, 236-247.
44. Schauer, R. Characterization of sialic acids. Meth. Enzymol., 1978, 50, 64-89.
45. Varki, A. and Kornfeld, S. An autosomal dominant gene regulates the extent of 9-O-acetylation of murine erthrocyte sialic acids. A probable explanation for the variation in capacity to activate the human alternate complement pathway. J. Exp. Med., 1980, 152, 532-544.
46. Neuberger, A. and Ratcliffe, W.A. The acid and enzymic hydrolysis of O-acetylated sialic acid residues from rabbit Tamm- Horsfall glycoprotein. Biochem. J., 1972, 129, 683-693.
47. Neuberger, A. and Ratcliffe, W.A. Kinetic studies on the acid hydrolysis of the methyl ketoside of unsubstituted and O-acetylated N-acetylneuraminic acid. Biochem. J., 1973, 133, 623-628.
48. Fenn, J.B.; Mann, M.; Meng, C.K.; Wong, S.F. and Whitehouse, C.M. Electrospray ionization for mass spectrometry of large biomolecules. Science, 1989, 246, 64-71.
49. Strupat, K.; Karas, M. and Hillenkamp, F. 2,5-Dihydroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry. Int. J. Mass Spectrom Ion Processes, 1991, 111, 89-102.
50. Kato, Y. and Numajiri, Y. Chloride attachment negative-ion mass spectra of sugars by combined liquid chromatography and atmospheric pressure chemical ionization mass spectrometry. J. Chromatogr., 1991, 562(1-2), 81-97.
51. Kohler, M. and Leary, J. LC/MS/MS of carbohydrates with postcolumn addition of metal chlorides using triaxial electrospray probe. Anal. Chem., 1995, 67(19), 3501-3508.
52. McIntosh, T.S.; Davis, H.M. and Matthews, D.E. A liquid chromatography-mass spectrometry method to measure stable isotopic tracer enrichments of glycerol and glucose in human serum. Anal. Biochem., 2002, 300(2), 163-169.
53. Zhu, J. and Cole, R.B. Ranking gas-phase acidities and chloride affinities of monosaccharides and linkage sepcificity in collision- induced decompositions of negative ion electrospray generated chloride adducts of oligosaccharides. J. Am. Soc. Mass Spectrom., 2001, 12, 1193-1204.
54. Harvey, D.J. 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, 622-630.
55. Yuan, J.; Hashii, N.; Kawasaki, N.; Itoh, S.; Kawanishi, T. and Hayakawa, T. Isotope tag method for the quantitative analysis of carbohydrates by liquid chromatography-mass spectrometry. J. Chromatogr. A., 2005, 1067, 145-152.
56. Liang, H.R.; Takagaki, T.; Foltz, R.L. and Bennett, P. Quantitative determination of endogenous sorbitol and fructose in human erythrocytes by atmospheric-pressure chemical ionization LC tandem mass spectrometry. J. Chromatogr. B., 2005, 824, 36-44.
57. Bruggink, C.; Maurer, R.; Herrmann, H.; Cavalli, S. and Hoefler, F. Analysis of carbohydrates by anion exchange chrmoatography and mass spectrometry. J. Chromatogr. A., 2005, 1085, 104-109.
58. + attachment. J. Am. Soc. Mass Spectrom., 2005, 16, 1805-1811.
59. Rogatsky, E.; Tomuta, V. and Stein, D.T. LC/MS quantitative study of glucose by iodine attachment. Anal. Chim. Acta., 2007, 591, 155-160.
60. Clarke, M.B.; Bezabeh, D.Z. and Howard, C.T. Determination of carbohydrates in tobacco products by liquid chromatography-mass spectrometry: A comparison with ion chromatography and application to product discrimination. J. Agric. Food Chem., 2006, 54, 1975-1981.
61. Wang, T.; Ham, P.K.-S.; Shi, H. and Ma, Y. Compositional monosaccharide analysis of transgenic corn glycoproteins by HPLC with fluorescence detection and LC-MS with sonic spray ionization. J. Chromatogr. Sci., 2007, 45, 200-206.
62. Hammad, L.A.; Saleh, M.M.; Novotny, M.V. and Mechref, Y. Multiple-reaction monitoring liquid chromatgraphy mass spectrometry for monosaccahride compositional analysis of glycoproteins. J. Am. Soc. Mass Spectrom., 2009, 20, 1224-1234.
63. Koizumi, K. High-performance liquid chromatographic separation of carbohydrates on graphitized carbon columns. J. Chromatogr., A., 1996, 720, 119-126.
64. Huang, Y.; Konse, T.; Mechref, Y. and Novotny, M.V. Matrix-assisted laser desorption/ionization mass spetrometry compatible - elimination of O-linked oligosaccharides. Rapid Commun. Mass Spectrom., 2002, 16, 1199-1204.
65. Hammad, L.A.; Derryberry, D.Z.; Jmeian, Y.R. and Mechref, Y. Quantification of monosaccharides through multiple-reaction monitoring liquid chromatography/mass spectrometry using an aminopropyl column. Rapid Commun. Mass Spectrom., 2010, 24(11), 1565-1574.
66. Linden, J.C. and Lawhead, C.L. Liquid chromatography of saccharides. J. Chromatogr., 1975, 105, 125-133.
67. Barton, F.E., Windham, W.R. and Himmelsbach, D.S. Analysis of neutral sugar hyrolysates of forage cell walls by high-pressure liquid chromatography. J. Agric. Food Chem., 1982, 30, 1119-1123.
68. Wei, Y.-A. and Fang, J.-N. Studies on the chromatographic behaviour of some uronic acids and neutral sugars on an amino-bonded phase column. J. Chromatogr., 1990, 513, 227-235.