Recent advances in the analysis of carbohydrates for biomedical use

Journal of Pharmaceutical and Biomedical Analysis

Volumn 55, Issue 4, 2011, Pages 702-727

  Yamada, Keita ^a,b   Kakehi, Kazuaki ^a  

^a KINKI UNIVERSITY   (Japan)

^b KAGAWA UNIVERSITY   (Japan)

Author keywords

Bioinformatics tools; Capillary microchip electrophoresis; Glycomics; HPLC; Mass spectrometry; Microarray

Indexed keywords

GLYCAN; GLYCOCONJUGATE; GLYCOLIPID; GLYCOPEPTIDE; GLYCOPROTEIN; PROTEOGLYCAN;

BIOINFORMATICS; CAPILLARY ELECTROPHORESIS; CARBOHYDRATE ANALYSIS; DATA BASE; DRUG DETERMINATION; DRUG LABELING; ELECTROSPRAY; GLYCOBIOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROARRAY ANALYSIS; MICROCHIP ELECTROPHORESIS; NONHUMAN; PRIORITY JOURNAL; REVIEW;

CARBOHYDRATES; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, ANALYTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMPUTATIONAL BIOLOGY; ELECTROPHORESIS, CAPILLARY; ELECTROPHORESIS, MICROCHIP; EQUIPMENT DESIGN; GLYCOPROTEINS; HUMANS; MASS SPECTROMETRY; OLIGONUCLEOTIDE ARRAY SEQUENCE ANALYSIS; POLYSACCHARIDES; SOLVENTS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 79955477752     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.02.003     Document Type: Review

References (284)

1. Peter-Katalinic J. Methods in enzymology: O-glycosylation of proteins. Methods Enzymol. 2005, 405:139-171.
2. Sugahara K., Yamashina I., De Waard P., Van Halbeek H., Vliegenthart J.F. Structural studies on sulfated glycopeptides from the carbohydrate-protein linkage region of chondroitin 4-sulfate proteoglycans of swarm rat chondrosarcoma. Demonstration of the structure Gal(4-O-sulfate)beta 1-3Gal beta 1-4XYL beta 1-O-Ser. J. Biol. Chem. 1988, 263:10168-10174.
3. Sugahara K., Kitagawa H. Recent advances in the study of the biosynthesis and functions of sulfated glycosaminoglycans. Curr. Opin. Struct. Biol. 2000, 10:518-527.
4. Ogata S.I., Muramatsu T., Kobata A. New structural characteristic of the large glycopeptides from transformed cells. Nature 1976, 259:580-582.
5. Brockhausen I. Pathways of O-glycan biosynthesis in cancer cells. Biochim. Biophys. Acta 1999, 1473:67-95.
6. Brockhausen I. Sulphotransferases acting on mucin-type oligosaccharides. Biochem. Soc. Trans. 2003, 31:318-325.
7. Brockhausen I. Glycodynamics of mucin biosynthesis in gastrointestinal tumor cells. Adv. Exp. Med. Biol. 2003, 535:163-188.
8. Springer G.F. T and Tn, general carcinoma autoantigens. Science 1984, 224:1198-1206.
9. Kumamoto K., Goto Y., Sekikawa K., Takenoshita S., Ishida N., Kawakita M., Kannagi R. Increased expression of UDP-galactose transporter messenger RNA in human colon cancer tissues and its implication in synthesis of Thomsen-Friedenreich antigen and sialyl Lewis A/X determinants. Cancer Res. 2001, 61:4620-4627.
10. Arnold J.N., Wormald M.R., Sim R.B., Rudd P.M., Dwek R.A. The impact of glycosylation on the biological function and structure of human immunoglobulins. Annu. Rev. Immunol. 2007, 25:21-50.
11. Lindahl B., Eriksson L., Spillmann D., Caterson B., Lindahl U. Selective loss of cerebral keratan sulfate in Alzheimer's disease. J. Biol. Chem. 1996, 271:16991-16994.
12. Rossi A., Bonaventure J., Delezoide A.L., Cetta G., Superti-Furga A. Undersulfation of proteoglycans synthesized by chondrocytes from a patient with achondrogenesis type 1B homozygous for an L483P substitution in the diastrophic dysplasia sulfate transporter. J. Biol. Chem. 1996, 271:18456-18464.
13. Iozzo R.V. Matrix proteoglycans: from molecular design to cellular function. Annu. Rev. Biochem. 1998, 67:609-652.
14. Theocharis A.D. Human colon adenocarcinoma is associated with specific post-translational modifications of versican and decorin. Biochim. Biophys. Acta 2002, 1588:165-172.
15. Domann P.J., Pardos-Pardos A.C., Fernandes D.L., Spencer D.I., Radcliffe C.M., Royle L., Dwek R.A., Rudd P.M. Separation-based glycoprofiling approaches using fluorescent labels. Proteomics 2007, 7:70-76.
16. Wada Y., Azadi P., Costello C.E., Dell A., Dwek R.A., Geyer H., Geyer R., Kakehi K., Karlsson N.G., Kato K., Kawasaki N., Khoo K.H., Kim S., Kondo A., Lattova E., Mechref Y., Miyoshi E., Nakamura K., Narimatsu H., Novotny M.V., Packer N.H., Perreault H., Peter-Katalinic J., Pohlentz G., Reinhold V.N., Rudd P.M., Suzuki A., Taniguchi N. Comparison of the methods for profiling glycoprotein glycans--HUPO Human Disease Glycomics/Proteome Initiative multi-institutional study. Glycobiology 2007, 17:411-422.
17. Wada Y., Dell A., Haslam S.M., Tissot B., Canis K., Azadi P., Backstrom M., Costello C.E., Hansson G.C., Hiki Y., Ishihara M., Ito H., Kakehi K., Karlsson N., Hayes C.E., Kato K., Kawasaki N., Khoo K.H., Kobayashi K., Kolarich D., Kondo A., Lebrilla C., Nakano M., Narimatsu H., Novak J., Novotny M.V., Ohno E., Packer N.H., Palaima E., Renfrow M.B., Tajiri M., Thomsson K.A., Yagi H., Yu S.Y., Taniguchi N. Comparison of methods for profiling O-glycosylation: Human Proteome Organisation Human Disease Glycomics/Proteome Initiative multi-institutional study of IgA1. Mol. Cell. Proteomics 2010, 9:719-727.
18. 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.
19. Ciucanu I., Caprita R. Per-O-methylation of neutral carbohydrates directly from aqueous samples for gas chromatography and mass spectrometry analysis. Anal. Chim. Acta 2007, 585:81-85.
20. Kang P., Mechref Y., Novotny M.V. High-throughput solid-phase permethylation of glycans prior to mass spectrometry. Rapid Commun. Mass. Spectrom. 2008, 22:721-734.
21. Renfrow M.B., Cooper H.J., Tomana M., Kulhavy R., Hiki Y., Toma K., Emmett M.R., Mestecky J., Marshall A.G., Novak J. Determination of aberrant O-glycosylation in the IgA1 hinge region by electron capture dissociation fourier transform-ion cyclotron resonance mass spectrometry. J. Biol. Chem. 2005, 280:19136-19145.
22. Fan X., She Y.M., Bagshaw R.D., Callahan J.W., Schachter H., Mahuran D.J. A method for proteomic identification of membrane-bound proteins containing Asn-linked oligosaccharides. Anal. Biochem. 2004, 332:178-186.
23. Bunkenborg J., Pilch B.J., Podtelejnikov A.V., Wisniewski J.R. Screening for N-glycosylated proteins by liquid chromatography mass spectrometry. Proteomics 2004, 4:454-465.
24. Kaji H., Yamauchi Y., Takahashi N., Isobe T. Mass spectrometric identification of N-linked glycopeptides using lectin-mediated affinity capture and glycosylation site-specific stable isotope tagging. Nat. Protoc. 2006, 1:3019-3027.
25. Blixt O., Head S., Mondala T., Scanlan C., Huflejt M.E., Alvarez R., Bryan M.C., Fazio F., Calarese D., Stevens J., Razi N., Stevens D.J., Skehel J.J., van Die I., Burton D.R., Wilson I.A., Cummings R., Bovin N., Wong C.H., Paulson J.C. Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proc. Natl. Acad. Sci. U.S.A. 2004, 101:17033-17038.
26. Fukui S., Feizi T., Galustian C., Lawson A.M., Chai W. Oligosaccharide microarrays for high-throughput detection and specificity assignments of carbohydrate-protein interactions. Nat. Biotechnol. 2002, 20:1011-1017.
27. Uchiyama N., Kuno A., Tateno H., Kubo Y., Mizuno M., Noguchi M., Hirabayashi J. Optimization of evanescent-field fluorescence-assisted lectin microarray for high-sensitivity detection of monovalent oligosaccharides and glycoproteins. Proteomics 2008, 8:3042-3050.
28. Kuno A., Uchiyama N., Koseki-Kuno S., Ebe Y., Takashima S., Yamada M., Hirabayashi J. Evanescent-field fluorescence-assisted lectin microarray: a new strategy for glycan profiling. Nat. Methods 2005, 2:851-856.
29. Yosizawa Z., Sato T., Schmid K. Hydrazinolysis of alpha-1-acid glycoprotein. Biochim. Biophys. Acta 1966, 121:417-420.
30. Takasaki S., Mizuochi T., Kobata A. Hydrazinolysis of asparagine-linked sugar chains to produce free oligosaccharides. Methods Enzymol. 1982, 83:263-268.
31. Takahashi N., Tomiya N. Analysis of N-linked oligosaccharides: application of glycoamidase A. Handbook of Endoglycosidases and Glycoamidases 1992, 199-332. CRC Press, Boca Raton. N. Takahashi, T. Muramatsu (Eds.).
32. Sheeley D.M., Reinhold V.N. Structural characterization of carbohydrate sequence, linkage, and branching in a quadrupole Ion trap mass spectrometer: neutral oligosaccharides and N-linked glycans. Anal. Chem. 1998, 70:3053-3059.
33. Kuster B., Wheeler S.F., Hunter A.P., Dwek R.A., Harvey D.J. 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, 250:82-101.
34. Sagi D., Kienz P., Denecke J., Marquardt T., Peter-Katalinic J. Glycoproteomics of N-glycosylation by in-gel deglycosylation and matrix-assisted laser desorption/ionisation-time of flight mass spectrometry mapping: application to congenital disorders of glycosylation. Proteomics 2005, 5:2689-2701.
35. Kamoda S., Nakanishi Y., Kinoshita M., Ishikawa R., Kakehi K. Analysis of glycoprotein-derived oligosaccharides in glycoproteins detected on two-dimensional gel by capillary electrophoresis using on-line concentration method. J. Chromatogr. A 2006, 1106:67-74.
36. Royle L., Campbell M.P., Radcliffe C.M., White D.M., Harvey D.J., Abrahams J.L., Kim Y.G., Henry G.W., Shadick N.A., Weinblatt M.E., Lee D.M., Rudd P.M., Dwek R.A. HPLC-based analysis of serum N-glycans on a 96-well plate platform with dedicated database software. Anal. Biochem. 2008, 376:1-12.
37. Cancilla M.T., Penn S.G., Lebrilla C.B. Alkaline degradation of oligosaccharides coupled with matrix-assisted laser desorption/ionization Fourier transform mass spectrometry: a method for sequencing oligosaccharides. Anal. Chem. 1998, 70:663-672.
38. Royle L., Mattu T.S., Hart E., Langridge J.I., Merry A.H., Murphy N., Harvey D.J., Dwek R.A., Rudd P.M. An analytical and structural database provides a strategy for sequencing O-glycans from microgram quantities of glycoproteins. Anal. Biochem. 2002, 304:70-90.
39. Merry A.H., Neville D.C., Royle L., Matthews B., Harvey D.J., Dwek R.A., Rudd P.M. Recovery of intact 2-aminobenzamide-labeled O-glycans released from glycoproteins by hydrazinolysis. Anal. Biochem. 2002, 304:91-99.
40. Kakehi K., Susami A., Taga A., Suzuki S., Honda S. High-performance capillary electrophoresis of O-glycosidically linked sialic acid-containing oligosaccharides in glycoproteins as their alditol derivatives with low-wavelength UV monitoring. J. Chromatogr. A 1994, 680:209-215.
41. Schulz B.L., Packer N.H., Karlsson N.G. Small-scale analysis of O-linked oligosaccharides from glycoproteins and mucins separated by gel electrophoresis. Anal. Chem. 2002, 74:6088-6097.
42. Backstrom M., Thomsson K.A., Karlsson H., Hansson G.C. Sensitive liquid chromatography-electrospray mass spectrometry allows for the analysis of the O-glycosylation of immunoprecipitated proteins from cells or tissues: application to MUC1 glycosylation in cancer. J. Proteome Res. 2009, 8:538-545.
43. Huang Y., Mechref Y., Novotny M.V. Microscale nonreductive release of O-linked glycans for subsequent analysis through MALDI mass spectrometry and capillary electrophoresis. Anal. Chem. 2001, 73:6063-6069.
44. Karlsson N.G., Packer N.H. Analysis of O-linked reducing oligosaccharides released by an in-line flow system. Anal. Biochem. 2002, 305:173-185.
45. Yamada K., Hyodo S., Matsuno Y.K., Kinoshita M., Maruyama S.Z., Osaka Y.S., Casal E., Lee Y.C., Kakehi K. Rapid and sensitive analysis of mucin-type glycans using an in-line flow glycan-releasing apparatus. Anal. Biochem. 2007, 371:52-61.
46. Sakaguchi H., Watanabe M., Ueoka C., Sugiyama E., Taketomi T., Yamada S., Sugahara K. Isolation of reducing oligosaccharide chains from the chondroitin/dermatan sulfate-protein linkage region and preparation of analytical probes by fluorescent labeling with 2-aminobenzamide. J. Biochem. 2001, 129:107-118.
47. Matsuno Y.K., Yamada K., Tanabe A., Kinoshita M., Maruyama S.Z., Osaka Y.S., Masuko T., Kakehi K. Development of an apparatus for rapid release of oligosaccharides at the glycosaminoglycan-protein linkage region in chondroitin sulfate-type proteoglycans. Anal. Biochem. 2007, 362:245-257.
48. Takagaki K., Iwafune M., Kakizaki I., Ishido K., Kato Y., Endo M. Cleavage of the xylosyl serine linkage between a core peptide and a glycosaminoglycan chain by cellulases. J. Biol. Chem. 2002, 277:18397-18403.
49. Takagaki K., Kon A., Kawasaki H., Nakamura T., Tamura S., Endo M. Isolation and characterization of Patnopecten mid-gut gland endo-beta-xylosidase active on peptidochondroitin sulfate. J. Biol. Chem. 1990, 265:854-860.
50. Yamada K., Hyodo S., Kinoshita M., Hayakawa T., Kakehi K. Hyphenated technique for releasing and MALDI MS analysis of O-glycans in mucin-type glycoprotein samples. Anal. Chem. 2010, 82:7436-7443.
51. Lattova E., Kapkova P., Krokhin O., Perreault H. Method for investigation of oligosaccharides from glycopeptides: direct determination of glycosylation sites in proteins. Anal. Chem. 2006, 78:2977-2984.
52. Lattova E., McKenzie E.J., Gruwel M.L., Spicer V., Goldman R., Perreault H. Mass spectrometric study of N-glycans from serum of woodchucks with liver cancer. Rapid Commun. Mass Spectrom. 2009, 23:2983-2995.
53. Bigge J.C., Patel T.P., Bruce J.A., Goulding P.N., Charles S.M., Parekh R.B. Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid. Anal. Biochem. 1995, 230:229-238.
54. Locke D., Bevans C.G., Wang L.X., Zhang Y., Harris A.L., Lee Y.C. Neutral, acidic, and basic derivatives of anthranilamide that confer different formal charge to reducing oligosaccharides. Carbohydr. Res. 2004, 339:221-231.
55. Hase S. Analysis of sugar chains by pyridylamination. Methods Mol. Biol. 1993, 14:69-80.
56. Hase S., Ikenaka T., Matsushima Y. Structure analyses of oligosaccharides by tagging of the reducing end sugars with a fluorescent compound. Biochem. Biophys. Res. Commun. 1978, 85:257-263.
57. Takahashi N., Lee K.B., Nakagawa H., Tsukamoto Y., Kawamura Y., Li Y.T., Lee Y.C. Enzymatic sialylation of N-linked oligosaccharides using an alpha-(2,3)-specific trans-sialidase from Trypanosoma cruzi: structural identification using a three-dimensional elution mapping technique. Anal. Biochem. 1995, 230:333-342.
58. Nakagawa H., Kawamura Y., Kato K., Shimada I., Arata Y., Takahashi N. Identification of neutral and sialyl N-linked oligosaccharide structures from human serum glycoproteins using three kinds of high-performance liquid chromatography. Anal. Biochem. 1995, 226:130-138.
59. Suzuki Y., Suzuki M., Ito E., Ishii H., Miseki K., Suzuki A. Convenient and rapid analysis of linkage isomers of fucose-containing oligosaccharides by matrix-assisted laser desorption/ionization quadrupole ion trap time-of-flight mass spectrometry. Glycoconj. J. 2005, 22:427-431.
60. Takegawa Y., Deguchi K., Ito S., Yoshioka S., Sano A., Yoshinari K., Kobayashi K., Nakagawa H., Monde K., Nishimura S. Assignment and quantification of 2-aminopyridine derivatized oligosaccharide isomers coeluted on reversed-phase HPLC/MS by MSn spectral library. Anal. Chem. 2004, 76:7294-7303.
61. Saldova R., Royle L., Radcliffe C.M., Abd Hamid U.M., Evans R., Arnold J.N., Banks R.E., Hutson R., Harvey D.J., Antrobus R., Petrescu S.M., Dwek R.A., Rudd P.M. Ovarian cancer is associated with changes in glycosylation in both acute-phase proteins and IgG. Glycobiology 2007, 17:1344-1356.
62. Storr S.J., Royle L., Chapman C.J., Hamid U.M., Robertson J.F., Murray A., Dwek R.A., Rudd P.M. The O-linked glycosylation of secretory/shed MUC1 from an advanced breast cancer patient's serum. Glycobiology 2008, 18:456-462.
63. Ritchie G., Harvey D.J., Stroeher U., Feldmann F., Feldmann H., Wahl-Jensen V., Royle L., Dwek R.A., Rudd P.M. Identification of N-glycans from Ebola virus glycoproteins by matrix-assisted laser desorption/ionisation time-of-flight and negative ion electrospray tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2010, 24:571-585.
64. Artemenko N.V., Campbell M.P., Rudd P.M. GlycoExtractor: a web-based interface for high throughput processing of HPLC-glycan data. J. Proteome Res. 2010, 9:2037-2041.
65. Anumula K.R., Dhume S.T. High resolution and high sensitivity methods for oligosaccharide mapping and characterization by normal phase high performance liquid chromatography following derivatization with highly fluorescent anthranilic acid. Glycobiology 1998, 8:685-694.
66. Kamoda S., Ishikawa R., Kakehi K. Capillary electrophoresis with laser-induced fluorescence detection for detailed studies on N-linked oligosaccharide profile of therapeutic recombinant monoclonal antibodies. J. Chromatogr. A 2006, 1133:332-339.
67. Yamada K., Kinoshita M., Hayakawa T., Nakaya S., Kakehi K. Comparative studies on the structural features of O-glycans between leukemia and epithelial cell lines. J. Proteome Res. 2009, 8:521-537.
68. Cheng H.L., Pai P.J., Her G.R. Linkage and branch determination of N-linked oligosaccharides using sequential degradation/closed-ring chromophore labeling/negative ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2007, 18:248-259.
69. Guttman A., Pritchett T. Capillary gel electrophoresis separation of high-mannose type oligosaccharides derivatized by 1-aminopyrene-3,6,8-trisulfonic acid. Electrophoresis 1995, 16:1906-1911.
70. Guttman A., Chen F.T., Evangelista R.A., Cooke N. High-resolution capillary gel electrophoresis of reducing oligosaccharides labeled with 1-aminopyrene-3,6,8-trisulfonate. Anal. Biochem. 1996, 233:234-242.
71. Guttman A., Starr C. Capillary and slab gel electrophoresis profiling of oligosaccharides. Electrophoresis 1995, 16:993-997.
72. Briggs J.B., Keck R.G., Ma S., Lau W., Jones A.J. An analytical system for the characterization of highly heterogeneous mixtures of N-linked oligosaccharides. Anal. Biochem. 2009, 389:40-51.
73. Gennaro L.A., Salas-Solano O. On-line CE-LIF-MS technology for the direct characterization of N-linked glycans from therapeutic antibodies. Anal. Chem. 2008, 80:3838-3845.
74. Volpi N. High-performance liquid chromatography and on-line mass spectrometry detection for the analysis of chondroitin sulfates/hyaluronan disaccharides derivatized with 2-aminoacridone. Anal. Biochem. 2010, 397:12-23.
75. Nakajima K., Oda Y., Kinoshita M., Kakehi K. Capillary affinity electrophoresis for the screening of post-translational modification of proteins with carbohydrates. J. Proteome Res. 2003, 2:81-88.
76. Li D.T., Her G.R. Structural analysis of chromophore-labeled disaccharides and oligosaccharides by electrospray ionization mass spectrometry and high-performance liquid chromatography/electrospray ionization mass spectrometry. J. Mass Spectrom. 1998, 33:644-652.
77. Guttman A., Chen F.T., Evangelista R.A. Separation of 1-aminopyrene-3,6,8-trisulfonate-labeled asparagine-linked fetuin glycans by capillary gel electrophoresis. Electrophoresis 1996, 17:412-417.
78. Okafo G., Langridge J., North S., Organ A., West A., Morris M., Camilleri P. High-performance liquid chromatographic analysis of complex N-linked glycans derivatized with 2-aminoacridone. Anal. Chem. 1997, 69:4985-4993.
79. Prater B.D., Anumula K.R., Hutchins J.T. Automated sample preparation facilitated by PhyNexus MEA purification system for oligosaccharide mapping of glycoproteins. Anal. Biochem. 2007, 369:202-209.
80. Honda S., Kakehi K., Takiura K. Studies of oligosaccharidelinkages by simultaneous determination of component aldehydes in dialdehyde fragemnts as (2.4-dinitrophenyl)hydrazones. Carbohydr. Res. 1976, 47:213-220.
81. Alpenfels W.F. A rapid and sensitive method for the determination of monosaccharides as their dansyl hydrazones by high-performance liquid chromatography. Anal. Biochem. 1981, 114:153-157.
82. Lattova E., Perreault H. Labelling saccharides with phenylhydrazine for electrospray and matrix-assisted laser desorption-ionization mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2003, 793:167-179.
83. Lattova E., Perreault H. Profiling of N-linked oligosaccharides using phenylhydrazine derivatization and mass spectrometry. J. Chromatogr. A 2003, 1016:71-87.
84. Kamoda S., Nakano M., Ishikawa R., Suzuki S., Kakehi K. Rapid and sensitive screening of N-glycans as 9-fluorenylmethyl derivatives by high-performance liquid chromatography: a method which can recover free oligosaccharides after analysis. J. Proteome Res. 2005, 4:146-152.
85. Nakano M., Higo D., Arai E., Nakagawa T., Kakehi K., Taniguchi N., Kondo A. Capillary electrophoresis-electrospray ionization mass spectrometry for rapid and sensitive N-glycan analysis of glycoproteins as 9-fluorenylmethyl derivatives. Glycobiology 2009, 19:135-143.
86. Furukawa J., Shinohara Y., Kuramoto H., Miura Y., Shimaoka H., Kurogochi M., Nakano M., Nishimura S. Comprehensive approach to structural and functional glycomics based on chemoselective glycoblotting and sequential tag conversion. Anal. Chem. 2008, 80:1094-1101.
87. Shimaoka H., Kuramoto H., Furukawa J., Miura Y., Kurogochi M., Kita Y., Hinou H., Shinohara Y., Nishimura S. One-pot solid-phase glycoblotting and probing by transoximization for high-throughput glycomics and glycoproteomics. Chemistry 2007, 13:1664-1673.
88. Ciucanu I. Per-O-methylation reaction for structural analysis of carbohydrates by mass spectrometry. Anal. Chim. Acta 2006, 576:147-155.
89. Zaia J. Mass spectrometry of oligosaccharides. Mass Spectrom. Rev. 2004, 23:161-227.
90. Guillard M., Gloerich J., Wessels H.J., Morava E., Wevers R.A., Lefeber D.J. Automated measurement of permethylated serum N-glycans by MALDI-linear ion trap mass spectrometry. Carbohydr. Res. 2009, 344:1550-1557.
91. Morelle W., Michalski J.C. Analysis of protein glycosylation by mass spectrometry. Nat. Protoc. 2007, 2:1585-1602.
92. Prien J.M., Ashline D.J., Lapadula A.J., Zhang H., Reinhold V.N. The high mannose glycans from bovine ribonuclease B isomer characterization by ion trap MS. J. Am. Soc. Mass Spectrom. 2009, 20:539-556.
93. Ciucanu I., Kerek F. A simple and rapid method for the permethylation of carbohydrates. Carbohydra. Res. 1984, 131:209-217.
94. Costello C.E., Contado-Miller J.M., Cipollo J.F. A glycomics platform for the analysis of permethylated oligosaccharide alditols. J. Am. Soc. Mass Spectrom. 2007, 18:1799-1812.
95. Easton R.L., Patankar M.S., Clark G.F., Morris H.R., Dell A. Pregnancy-associated changes in the glycosylation of tamm-horsfall glycoprotein. Expression of sialyl Lewis(x) sequences on core 2 type O-glycans derived from uromodulin. J. Biol. Chem. 2000, 275:21928-21938.
96. Kang P., Mechref Y., Klouckova I., Novotny M.V. Solid-phase permethylation of glycans for mass spectrometric analysis. Rapid Commun. Mass Spectrom. 2005, 19:3421-3428.
97. Kang P., Mechref Y., Kyselova Z., Goetz J.A., Novotny M.V. Comparative glycomic mapping through quantitative permethylation and stable-isotope labeling. Anal. Chem. 2007, 79:6064-6073.
98. Lei M., Mechref Y., Novotny M.V. Structural analysis of sulfated glycans by sequential double-permethylation using methyl iodide and deuteromethyl iodide. J. Am. Soc. Mass Spectrom. 2009, 20:1660-1671.
99. Wheeler S.F., Domann P., Harvey D.J. 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.
100. Toyoda M., Ito H., Matsuno Y.K., Narimatsu H., Kameyama A. Quantitative derivatization of sialic acids for the detection of sialoglycans by MALDI MS. Anal. Chem. 2008, 80:5211-5218.
101. Isailovic D., Kurulugama R.T., Plasencia M.D., Stokes S.T., Kyselova Z., Goldman R., Mechref Y., Novotny M.V., Clemmer D.E. Profiling of human serum glycans associated with liver cancer and cirrhosis by IMS-MS. J. Proteome Res. 2008, 7:1109-1117.
102. Plasencia M.D., Isailovic D., Merenbloom S.I., Mechref Y., Novotny M.V., Clemmer D.E. Resolving and assigning N-linked glycan structural isomers from ovalbumin by IMS-MS. J. Am. Soc. Mass Spectrom. 2008, 19:1706-1715.
103. Harvey D.J. Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: an update for the period 2005-2006. Mass Spectrom. Rev. 2010.
104. Tholey A., Heinzle E. Ionic (liquid) matrices for matrix-assisted laser desorption/ionization mass spectrometry-applications and perspectives. Anal. Bioanal. Chem. 2006, 386:24-37.
105. Laremore T.N., Zhang F., Linhardt R.J. Ionic liquid matrix for direct UV-MALDI-TOF-MS analysis of dermatan sulfate and chondroitin sulfate oligosaccharides. Anal. Chem. 2007, 79:1604-1610.
106. C. Przybylski, F. Gonnet, D. Bonnaffe, Y. Hersant, H. Lortat-Jacob, R. Daniel, HABA-based ionic liquid matrices for UV-MALDI-MS analysis of heparin and heparan sulfate oligosaccharides, Glycobiology 20 224-234.
107. Cooke C.L., An H.J., Kim J., Solnick J.V., Lebrilla C.B. Method for profiling mucin oligosaccharides from gastric biopsies of rhesus monkeys with and without Helicobacter pylori infection. Anal. Chem. 2007, 79:8090-8097.
108. Cooke C.L., An H.J., Kim J., Canfield D.R., Torres J., Lebrilla C.B., Solnick J.V. Modification of gastric mucin oligosaccharide expression in rhesus macaques after infection with Helicobacter pylori. Gastroenterology 2009, 137:1061-1071. 1071 e1-e8.
109. An H.J., Miyamoto S., Lancaster K.S., Kirmiz C., Li B., Lam K.S., Leiserowitz G.S., Lebrilla C.B. Profiling of glycans in serum for the discovery of potential biomarkers for ovarian cancer. J. Proteome Res. 2006, 5:1626-1635.
110. Kirmiz C., Li B., An H.J., Clowers B.H., Chew H.K., Lam K.S., Ferrige A., Alecio R., Borowsky A.D., Sulaimon S., Lebrilla C.B., Miyamoto S. A serum glycomics approach to breast cancer biomarkers. Mol. Cell. Proteomics 2007, 6:43-55.
111. Kyselova Z., Mechref Y., Kang P., Goetz J.A., Dobrolecki L.E., Sledge G.W., Schnaper L., Hickey R.J., Malkas L.H., Novotny M.V. Breast cancer diagnosis and prognosis through quantitative measurements of serum glycan profiles. Clin. Chem. 2008, 54:1166-1175.
112. Alley W.R., Novotny M.V. Glycomic analysis of sialic acid linkages in glycans derived from blood serum glycoproteins. J. Proteome Res. 2010, 9:3062-3072.
113. Goetz J.A., Mechref Y., Kang P., Jeng M.H., Novotny M.V. Glycomic profiling of invasive and non-invasive breast cancer cells. Glycoconj. J. 2009, 26:117-131.
114. Goldman R., Ressom H.W., Varghese R.S., Goldman L., Bascug G., Loffredo C.A., Abdel-Hamid M., Gouda I., Ezzat S., Kyselova Z., Mechref Y., Novotny M.V. Detection of hepatocellular carcinoma using glycomic analysis. Clin. Cancer Res. 2009, 15:1808-1813.
115. Hammoud Z.T., Mechref Y., Hussein A., Bekesova S., Zhang M., Kesler K.A., Novotny M.V. Comparative glycomic profiling in esophageal adenocarcinoma. J. Thorac. Cardiovasc. Surg. 2010, 139:1216-1223.
116. Harvey D.J. Collision-induced fragmentation of underivatized N-linked carbohydrates ionized by electrospray. J. Mass Spectrom. 2000, 35:1178-1190.
117. 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.
118. Takegawa Y., Ito H., Keira T., Deguchi K., Nakagawa H., Nishimura S. Profiling of N- and O-glycopeptides of erythropoietin by capillary zwitterionic type of hydrophilic interaction chromatography/electrospray ionization mass spectrometry. J. Sep. Sci. 2008, 31:1585-1593.
119. Thomsson K.A., Karlsson N.G., 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.
120. Hanisch F.G., Muller S. Analysis of methylated O-glycan alditols by reversed-phase NanoLC coupled CAD-ESI mass spectrometry. Methods Mol. Biol. 2009, 534:107-115.
121. Volpi N. On-line HPLC/ESI-MS separation and characterization of hyaluronan oligosaccharides from 2-mers to 40-mers. Anal. Chem. 2007, 79:6390-6397.
122. N. Volpi, R.J. Linhardt, High-performance liquid chromatography-mass spectrometry for mapping and sequencing glycosaminoglycan-derived oligosaccharides, Nat. Protoc. 5 993-1004.
123. Zamfir A.D., Bindila L., Lion N., Allen M., Girault H.H., Peter-Katalinic J. Chip electrospray mass spectrometry for carbohydrate analysis. Electrophoresis 2005, 26:3650-3673.
124. Bindila L., Peter-Katalinic J. Chip-mass spectrometry for glycomic studies. Mass Spectrom. Rev. 2009, 28:223-253.
125. Zamfir A., Vakhrushev S., Sterling A., Niebel H.J., Allen M., Peter-Katalinic J. Fully automated chip-based mass spectrometry for complex carbohydrate system analysis. Anal. Chem. 2004, 76:2046-2054.
126. Flangea C., Schiopu C., Sisu E., Serb A., Przybylski M., Seidler D.G., Zamfir A.D. Determination of sulfation pattern in brain glycosaminoglycans by chip-based electrospray ionization ion trap mass spectrometry. Anal. Bioanal. Chem. 2009, 395:2489-2498.
127. Chu C.S., Ninonuevo M.R., Clowers B.H., Perkins P.D., An H.J., Yin H., Killeen K., Miyamoto S., Grimm R., Lebrilla C.B. Profile of native N-linked glycan structures from human serum using high performance liquid chromatography on a microfluidic chip and time-of-flight mass spectrometry. Proteomics 2009, 9:1939-1951.
128. Ninonuevo M., An H., Yin H., Killeen K., Grimm R., Ward R., German B., Lebrilla C. Nanoliquid chromatography-mass spectrometry of oligosaccharides employing graphitized carbon chromatography on microchip with a high-accuracy mass analyzer. Electrophoresis 2005, 26:3641-3649.
129. Staples G.O., Bowman M.J., Costello C.E., Hitchcock A.M., Lau J.M., Leymarie N., Miller C., Naimy H., Shi X., Zaia J. A chip-based amide-HILIC LC/MS platform for glycosaminoglycan glycomics profiling. Proteomics 2009, 9:686-695.
130. Wuhrer M., de Boer A.R., Deelder A.M. Structural glycomics using hydrophilic interaction chromatography (HILIC) with mass spectrometry. Mass Spectrom. Rev. 2009, 28:192-206.
131. Alpert A.J., Shukla M., Shukla A.K., Zieske L.R., Yuen S.W., Ferguson M.A., Mehlert A., Pauly M., Orlando R. Hydrophilic-interaction chromatography of complex carbohydrates. J. Chromatogr. A 1994, 676. 191-122.
132. Hemstrom P., Irgum K. Hydrophilic interaction chromatography. J. Sep. Sci. 2006, 29:1784-1821.
133. Takegawa Y., Deguchi K., Keira T., Ito H., Nakagawa H., Nishimura S. Separation of isomeric 2-aminopyridine derivatized N-glycans and N-glycopeptides of human serum immunoglobulin G by using a zwitterionic type of hydrophilic-interaction chromatography. J. Chromatogr. A 2006, 1113:177-181.
134. Anumula K.R. Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Anal. Biochem. 2006, 350:1-23.
135. Deguchi K., Keira T., Yamada K., Ito H., Takegawa Y., Nakagawa H., Nishimura S. Two-dimensional hydrophilic interaction chromatography coupling anion-exchange and hydrophilic interaction columns for separation of 2-pyridylamino derivatives of neutral and sialylated N-glycans. J. Chromatogr. A 2008, 1189:169-174.
136. Takegawa Y., Deguchi K., Ito H., Keira T., Nakagawa H., Nishimura S. Simple separation of isomeric sialylated N-glycopeptides by a zwitterionic type of hydrophilic interaction chromatography. J. Sep. Sci. 2006, 29:2533-2540.
137. Anumula K.R. Unique anthranilic acid chemistry facilitates profiling and characterization of Ser/Thr-linked sugar chains following hydrazinolysis. Anal. Biochem. 2008, 373:104-111.
138. Campbell M.P., Royle L., Radcliffe C.M., Dwek R.A., Rudd P.M. GlycoBase and autoGU: tools for HPLC-based glycan analysis. Bioinformatics 2008, 24:1214-1216.
139. Ercan A., Cui J., Chatterton D.E., Deane K.D., Hazen M.M., Brintnell W., O'Donnell C.I., Derber L.A., Weinblatt M.E., Shadick N.A., Bell D.A., Cairns E., Solomon D.H., Holers V.M., Rudd P.M., Lee D.M. Aberrant IgG galactosylation precedes disease onset, correlates with disease activity, and is prevalent in autoantibodies in rheumatoid arthritis. Arthritis Rheum 2010, 62:2239-2248.
140. Hitchcock A.M., Yates K.E., Costello C.E., Zaia J. Comparative glycomics of connective tissue glycosaminoglycans. Proteomics 2008, 8:1384-1397.
141. Zauner G., Koeleman C.A., Deelder A.M., Wuhrer M. Protein glycosylation analysis by HILIC-LC-MS of Proteinase K-generated N- and O-glycopeptides. J. Sep. Sci. 2010, 33:903-910.
142. Wohlgemuth J., Karas M., Jiang W., Hendriks R., Andrecht S. Enhanced glyco-profiling by specific glycopeptide enrichment and complementary monolithic nano-LC (ZIC-HILIC/RP18e)/ESI-MS analysis. J. Sep. Sci. 2010, 33:880-890.
143. Hase S., Ibuki T., Ikenaka T. Reexamination of the pyridylamination used for fluorescence labeling of oligosaccharides and its application to glycoproteins. J. Biochem. 1984, 95:197-203.
144. Naka R., Kamoda S., Ishizuka A., Kinoshita M., Kakehi K. Analysis of total N-glycans in cell membrane fractions of cancer cells using a combination of serotonin affinity chromatography and normal phase chromatography. J. Proteome Res. 2006, 5:88-97.
145. Pabst M., Altmann F. Influence of electrosorption, solvent, temperature, and ion polarity on the performance of LC-ESI-MS using graphitic carbon for acidic oligosaccharides. Anal. Chem. 2008, 80:7534-7542.
146. Hashii N., Kawasaki N., Itoh S., Hyuga M., Kawanishi T., Hayakawa T. Glycomic/glycoproteomic analysis by liquid chromatography/mass spectrometry: analysis of glycan structural alteration in cells. Proteomics 2005, 5:4665-4672.
147. Itoh S., Kawasaki N., Hashii N., Harazono A., Matsuishi Y., Hayakawa T., Kawanishi T. N-linked oligosaccharide analysis of rat brain Thy-1 by liquid chromatography with graphitized carbon column/ion trap-Fourier transform ion cyclotron resonance mass spectrometry in positive and negative ion modes. J. Chromatogr. A 2006, 1103:296-306.
148. Kawasaki N., Itoh S., Ohta M., Hayakawa T. Microanalysis of N-linked oligosaccharides in a glycoprotein by capillary liquid chromatography/mass spectrometry and liquid chromatography/tandem mass spectrometry. Anal. Biochem. 2003, 316:15-22.
149. Thomsson K.A., Prakobphol A., Leffler H., Reddy M.S., Levine M.J., Fisher S.J., Hansson G.C. The salivary mucin MG1 (MUC5B) carries a repertoire of unique oligosaccharides that is large and diverse. Glycobiology 2002, 12:1-14.
150. Thomsson K.A., Schulz B.L., Packer N.H., Karlsson N.G. MUC5B glycosylation in human saliva reflects blood group and secretor status. Glycobiology 2005, 15:791-804.
151. Karlsson N.G., Thomsson K.A. Salivary MUC7 is a major carrier of blood group I type O-linked oligosaccharides serving as the scaffold for sialyl Lewis x. Glycobiology 2009, 19:288-300.
152. Stadlmann J., Pabst M., Kolarich D., Kunert R., Altmann F. Analysis of immunoglobulin glycosylation by LC-ESI-MS of glycopeptides and oligosaccharides. Proteomics 2008, 8:2858-2871.
153. Gornik O., Royle L., Harvey D.J., Radcliffe C.M., Saldova R., Dwek R.A., Rudd P., Lauc G. Changes of serum glycans during sepsis and acute pancreatitis. Glycobiology 2007, 17:1321-1332.
154. Limtiaco J.F., Jones C.J., Larive C.K. Characterization of heparin impurities with HPLC-NMR using weak anion exchange chromatography. Anal. Chem. 2009, 81:10116-10123.
155. M. Pucic, S. Pinto, M. Novokmet, A. Knezevic, O. Gornik, O. Polasek, K. Vlahovicek, W. Wang, P.M. Rudd, A.F. Wright, H. Campbell, I. Rudan, G. Lauc, Common aberrations from the normal human plasma N-glycan profile. Glycobiology 20 970-975.
156. Takahashi N. Three-dimensional mapping of N-linked oligosaccharides using anion-exchange, hydrophobic and hydrophilic interaction modes of high-performance liquid chromatography, J. Chromatogr. A 1996, 720:217-225.
157. Su Y., Royle L., Radcliffe C.M., Harvey D.J., Dwek R.A., Martinez-Pomares L., Rudd P.M. Detailed N-glycan analysis of mannose receptor purified from murine spleen indicates tissue specific sialylation. Biochem. Biophys. Res. Commun. 2009, 384:436-443.
158. Volpi N., Bolognani L. Glycosaminoglycans and proteins: different behaviours in high-performance size-exclusion chromatography. J. Chromatogr. 1993, 630:390-396.
159. Maccari F., Volpi N. Structural characterization of the skin glycosaminoglycans in patients with pseudoxanthoma elasticum. Int. J. Dermatol. 2008, 47:1024-1027.
160. Coppa G.V., Buzzega D., Zampini L., Maccari F., Galeazzi T., Pederzoli F., Gabrielli O., Volpi N. Effect of six years of enzyme-replacement therapy on plasma and urine glycosaminoglycans in attenuated MPS I patients. Glycobiology 2010, 20:1259-1273.
161. Berry L.R., Puzzuoli F.V., Hatton M.W. On the interaction between 5-hydroxytryptamine and N-acetylneuraminic acid under aqueous conditions. Can. J. Biochem. Cell Biol. 1985, 63:757-763.
162. Sturgeon R.J., Sturgeon C.M. Affinity chromatography of sialoglycoproteins, utilising the interaction of serotonin with n-acetylneuraminic acid and its derivatives. Carbohydr. Res. 1982, 103:213-219.
163. el Rassi Z., Horvath C., Yu R.K., Ariga T. High-performance liquid chromatography of sialooligosaccharides and gangliosides. J. Chromatogr. 1989, 488:229-236.
164. Takahashi N., Wada Y., Awaya J., Kurono M., Tomiya N. Two-dimensional elution map of GalNAc-containing N-linked oligosaccharides. Anal. Biochem. 1993, 208:96-109.
165. Takahashi N., Nakagawa H., Fujikawa K., Kawamura Y., Tomiya N. Three-dimensional elution mappong of pyridylaminated N-linked neutral and sialyl oligosaccharides. Anal. Biochem. 1995, 226:139-146.
166. Ishizuka A., Hashimto Y., Naka R., Kinoshita M., Kakehi K., Seino J., Funakoshi Y., Suzuki T., Kameyama A., Narimatsu H. Accumulation of free complex-type N-glycans in MKN7 and MKN45 stomach cancer cells. Biochem. J. 2008, 413:227-237.
167. Kamoda S., Kakehi K. Capillary electrophoresis for the analysis of glycoprotein pharmaceuticals. Electrophoresis 2006, 27:2495-2504.
168. Kamoda S., Kakehi K. Evaluation of glycosylation for quality assurance of antibody pharmaceuticals by capillary electrophoresis. Electrophoresis 2008, 29:3595-3604.
169. Zamfir A., Peter-Katalinic J. Capillary electrophoresis-mass spectrometry for glycoscreening in biomedical research. Electrophoresis 2004, 25:1949-1963.
170. Amon S., Zamfir A.D., Rizzi A. Glycosylation analysis of glycoproteins and proteoglycans using capillary electrophoresis-mass spectrometry strategies. Electrophoresis 2008, 29:2485-2507.
171. Okafo G., Burrow L., Carr S.A., Roberts G.D., Johnson W., Camilleri P. A coordinated high-performance liquid chromatographic, capillary electrophoretic, and mass spectrometric approach for the analysis of oligosaccharide mixtures derivatized with 2-aminoacridone. Anal. Chem. 1996, 68:4424-4430.
172. Okafo G.N., Burrow L.M., Neville W., Truneh A., Smith R.A., Reff M., Camilleri P. Simple differentiation between core-fucosylated and nonfucosylated glycans by capillary electrophoresis. Anal. Biochem. 1996, 240:68-74.
173. Matsuno Y.K., Nakamura H., Kakehi K. Comparative studies on the analysis of urinary trypsin inhibitor (ulinastatin) preparations. Electrophoresis 2006, 27:2486-2494.
174. Klockow A., Amado R., Widmer H.M., Paulus A. Separation of 8-aminonaphthalene-1,3,6-trisulfonic acid-labelled neutral and sialylated N-linked complex oligosaccharides by capillary electrophoresis. J. Chromatogr. A 1995, 716:241-247.
175. Che F.Y., Song J.F., Zeng R., Wang K.Y., Xia Q.C. Analysis of 8-aminonaphthalene-1,3,6-trisulfonate-derivatized oligosaccharides by capillary electrophoresis-electrospray ionization quadrupole ion trap mass spectrometry. J. Chromatogr. A 1999, 858:229-238.
176. Laroy W., Contreras R., Callewaert N. Glycome mapping on DNA sequencing equipment. Nat. Protoc. 2006, 1:397-405.
177. Callewaert N., Geysens S., Molemans F., Contreras R. Ultrasensitive profiling and sequencing of N-linked oligosaccharides using standard DNA-sequencing equipment. Glycobiology 2001, 11:275-281.
178. Chen F.T., Evangelista R.A. Profiling glycoprotein n-linked oligosaccharide by capillary electrophoresis. Electrophoresis 1998, 19:2639-2644.
179. Tegeler T.J., Mechref Y., Boraas K., Reilly J.P., Novotny M.V. Microdeposition device interfacing capillary electrochromatography and microcolumn liquid chromatography with matrix-assisted laser desorption/ionization mass spectrometry. Anal. Chem. 2004, 76:6698-6706.
180. Que A.H., Mechref Y., Huang Y., Taraszka J.A., Clemmer D.E., Novotny M.V. Coupling capillary electrochromatography with electrospray Fourier transform mass spectrometry for characterizing complex oligosaccharide pools. Anal. Chem. 2003, 75:1684-1690.
181. Hirabayashi J. Lectin-based structural glycomics: glycoproteomics and glycan profiling. Glycoconj. J. 2004, 21:35-40.
182. Nakajima K., Kinoshita M., Matsushita N., Urashima T., Suzuki M., Suzuki A., Kakehi K. Capillary affinity electrophoresis using lectins for the analysis of milk oligosaccharide structure and its application to bovine colostrum oligosaccharides. Anal. Biochem. 2006, 348:105-114.
183. Nakajima K., Kinoshita M., Oda Y., Masuko T., Kaku H., Shibuya N., Kakehi K. Screening method of carbohydrate-binding proteins in biological sources by capillary affinity electrophoresis and its application to determination of Tulipa gesneriana agglutinin in tulip bulbs. Glycobiology 2004, 14:793-804.
184. Kim J.B., Otsuka K., Terabe S. On-line sample preconcentration in micellar electrokinetic chromatography using ion-pair reagents. J. Chromatogr. A 2002, 979:131-136.
185. Quirino J.P., Kim J.B., Terabe S. Sweeping: concentration mechanism and applications to high-sensitivity analysis in capillary electrophoresis. J. Chromatogr. A 2002, 965:357-373.
186. Zhang C.X., Thormann W. Head-column field-amplified sample stacking in binary system capillary electrophoresis. 2. Optimization with a preinjection plug and application to micellar electrokinetic chromatography. Anal. Chem. 1998, 70:540-548.
187. Callewaert N., Van Vlierberghe H., Van Hecke A., Laroy W., Delanghe J., Contreras R. Noninvasive diagnosis of liver cirrhosis using DNA sequencer-based total serum protein glycomics. Nat. Med. 2004, 10:429-434.
188. Vanderschaeghe D., Laroy W., Sablon E., Halfon P., Van Hecke A., Delanghe J., Callewaert N. GlycoFibroTest is a highly performant liver fibrosis biomarker derived from DNA sequencer-based serum protein glycomics. Mol. Cell. Proteomics 2009, 8:986-994.
189. Honda S. Monosaccharide analysis by capillary electrophoresis. Methods Mol. Biol. 2003, 213:81-92.
190. Tseng H.M., Gattolin S., Pritchard J., Newbury H.J., Barrett D.A. Analysis of mono-, di- and oligosaccharides by CE using a two-stage derivatization method and LIF detection. Electrophoresis 2009, 30:1399-1405.
191. Che F.Y., Liu Z.Y., Wang K.Y., Xia Q.C. Analysis of Monosaccharides Derivatized with 2-aminoacridone by Capillary Electrophoresis. Sheng Wu Hua Xue Yu Sheng Wu Wu Li Xue Bao (Shanghai) 1998, 30:251-256.
192. Rustighi I., Campa C., Rossi M., Semeraro S., Vetere A., Gamini A. Analysis of N-acetylaminosugars by CE: a comparative derivatization study. Electrophoresis 2009, 30:2632-2639.
193. Kodama S., Aizawa S., Taga A., Yamashita T., Kemmei T., Yamamoto A., Hayakawa K. Simultaneous chiral resolution of monosaccharides as 8-aminonaphthalene-1,3,6-trisulfonate derivatives by ligand-exchange CE using borate as a central ion of the chiral selector. Electrophoresis 2007, 28:3930-3933.
194. Kodama S., Aizawa S., Taga A., Yamashita T., Yamamoto A. Chiral resolution of monosaccharides as 1-phenyl-3-methyl-5-pyrazolone derivatives by ligand-exchange CE using borate anion as a central ion of the chiral selector. Electrophoresis 2006, 27:4730-4734.
195. Yamada K., Watanabe S., Kita S., Kinoshita M., Hayakawa T., Kakehi K. Determination of Tn antigen released from cultured cancer cells by capillary electrophoresis. Anal. Biochem. 2010, 396:161-163.
196. Konska G., Guerry M., Caldefie-Chezet F., De Latour M., Guillot J. Study of the expression of Tn antigen in different types of human breast cancer cells using VVA-B4 lectin. Oncol. Rep. 2006, 15:305-310.
197. Ju T., Cummings R.D. A unique molecular chaperone Cosmc required for activity of the mammalian core 1 beta 3-galactosyltransferase. Proc. Natl. Acad. Sci. U.S.A. 2002, 99:16613-16618.
198. Trainer D.L., Kline T., McCabe F.L., Faucette L.F., Feild J., Chaikin M., Anzano M., Rieman D., Hoffstein S., Li D.J., et al. Biological characterization and oncogene expression in human colorectal carcinoma cell lines. Int. J. Cancer 1988, 41:287-296.
199. Dordal M.S., Wang F.F., Goldwasser E. The role of carbohydrate in erythropoietin action. Endocrinology 1985, 116:2293-2299.
200. Bietlot H.P., Girard M. Analysis of recombinant human erythropoietin in drug formulations by high-performance capillary electrophoresis. J. Chromatogr. A 1997, 759:177-184.
201. Cifuentes A., Moreno-Arribas M.V., de Frutos M., Diez-Masa J.C. Capillary isoelectric focusing of erythropoietin glycoforms and its comparison with flat-bed isoelectric focusing and capillary zone electrophoresis. J. Chromatogr. A 1999, 830:453-643.
202. Kinoshita M., Murakami E., Oda Y., Funakubo T., Kawakami D., Kakehi K., Kawasaki N., Morimoto K., Hayakawa T. Comparative studies on the analysis of glycosylation heterogeneity of sialic acid-containing glycoproteins using capillary electrophoresis. J. Chromatogr. A 2000, 866:261-271.
203. Leader K.A., Kumpel B.M., Hadley A.G., Bradley B.A. Functional interactions of aglycosylated monoclonal anti-D with Fc gamma RI+ and Fc gamma RIII+ cells. Immunology 1991, 72:481-485.
204. Umana P., Jean-Mairet J., Moudry R., Amstutz H., Bailey J.E. Engineered glycoforms of an antineuroblastoma IgG1 with optimized antibody-dependent cellular cytotoxic activity. Nat. Biotechnol. 1999, 17:176-180.
205. Leatherbarrow R.J., Rademacher T.W., Dwek R.A., Woof J.M., Clark A., Burton D.R., Richardson N., Feinstein A. Effector functions of a monoclonal aglycosylated mouse IgG2a: binding and activation of complement component C1 and interaction with human monocyte Fc receptor. Mol. Immunol. 1985, 22:407-415.
206. Tao M.H., Morrison S.L. Studies of aglycosylated chimeric mouse-human IgG. Role of carbohydrate in the structure and effector functions mediated by the human IgG constant regio. J. Immunol. 1989, 143:2595-2601.
207. Chee Furng Wong D., Tin Kam Wong K., Tang Goh L., Kiat Heng C., Gek Sim Yap M. Impact of dynamic online fed-batch strategies on metabolism, productivity and N-glycosylation quality in CHO cell cultures. Biotechnol. Bioeng. 2005, 89:164-177.
208. Volpi N., Maccari F., Linhardt R.J. Quantitative capillary electrophoresis determination of oversulfated chondroitin sulfate as a contaminant in heparin preparations. Anal. Biochem. 2009, 388:140-145.
209. Kakoi N., Kinoshita M., Kawasaki N., Yamaguchi T., Hayakawa T., Kakehi K. Capillary electrophoresis analysis of contaminants in heparin sodium for the Japanese pharmacopoeia purity test. Yakugaku Zasshi 2009, 129:1255-1264.
210. Guerrini M., Zhang Z., Shriver Z., Naggi A., Masuko S., Langer R., Casu B., Linhardt R.J., Torri G., Sasisekharan R. Orthogonal analytical approaches to detect potential contaminants in heparin. Proc. Natl. Acad. Sci. U.S.A. 2009, 106:16956-16961.
211. Somsen G.W., Tak Y.H., Torano J.S., Jongen P.M., de Jong G.J. Determination of oversulfated chondroitin sulfate and dermatan sulfate impurities in heparin by capillary electrophoresis. J. Chromatogr. A 2009, 1216:4107-4112.
212. Mechref Y., Novotny M.V. Glycomic analysis by capillary electrophoresis-mass spectrometry. Mass Spectrom. Rev. 2009, 28:207-222.
213. von Brocke A., Nicholson G., Bayer E. Recent advances in capillary electrophoresis/electrospray-mass spectrometry. Electrophoresis 2001, 22:1251-1266.
214. Janini G.M., Zhou M., Yu L.R., Blonder J., Gignac M., Conrads T.P., Issaq H.J., Veenstra T.D. On-column sample enrichment for capillary electrophoresis sheathless electrospray ionization mass spectrometry: evaluation for peptide analysis and protein identification. Anal. Chem. 2003, 75:5984-5993.
215. Stutz H. Advances in the analysis of proteins and peptides by capillary electrophoresis with matrix-assisted laser desorption/ionization and electrospray-mass spectrometry detection. Electrophoresis 2005, 26:1254-1290.
216. Sandra K., Van Beeumen J., Stals I., Sandra P., Claeyssens M., Devreese B. Characterization of cellobiohydrolase I N-glycans differentiation of their phosphorylated isomers by capillary electrophoresis-Q-Trap mass spectrometry. Anal. Chem. 2004, 76:5878-5886.
217. Dang F., Kakehi K., Nakajima K., Shinohara Y., Ishikawa M., Kaji N., Tokeshi M., Baba Y. Rapid analysis of oligosaccharides derived from glycoproteins by microchip electrophoresis. J. Chromatogr. A 2006, 1109:138-143.
218. Zhuang Z., Starkey J.A., Mechref Y., Novotny M.V., Jacobson S.C. Electrophoretic analysis of N-glycans on microfluidic devices. Anal. Chem. 2007, 79:7170-7175.
219. Callewaert N., Contreras R., Mitnik-Gankin L., Carey L., Matsudaira P., Ehrlich D. Total serum protein N-glycome profiling on a capillary electrophoresis-microfluidics platform. Electrophoresis 2004, 25:3128-3131.
220. Matsuno Y.K., Kinoshita M., Kakehi K. Fast analysis of glycosaminoglycans by microchip electrophoresis with in situ fluorescent detection using ethidium bromide. J. Pharm. Biomed. Anal. 2005, 37:429-436.
221. Matsuno Y.K., Kinoshita M., Kakehi K. Electrophoretic analysis of di- and oligosaccharides derived from glycosaminoglycans on microchip format. J. Pharm. Biomed. Anal. 2004, 36:9-15.
222. Sharon N. Lectins: past, present and future. Biochem. Soc. Trans. 2008, 36:1457-1460.
223. Gemeiner P., Mislovicova D., Tkac J., Svitel J., Patoprsty V., Hrabarova E., Kogan G., Kozar T. Lectinomics II. A highway to biomedical/clinical diagnostics. Biotechnol. Adv. 2009, 27:1-15.
224. Hsu K.L., Mahal L.K. Sweet tasting chips: microarray-based analysis of glycans. Curr. Opin. Chem. Biol. 2009, 13:427-432.
225. Angeloni S., Ridet J.L., Kusy N., Gao H., Crevoisier F., Guinchard S., Kochhar S., Sigrist H., Sprenger N. Glycoprofiling with micro-arrays of glycoconjugates and lectins. Glycobiology 2005, 15:31-41.
226. Pilobello K.T., Krishnamoorthy L., Slawek D., Mahal L.K. Development of a lectin microarray for the rapid analysis of protein glycopatterns. Chembiochem 2005, 6:985-989.
227. Kuno A., Kato Y., Matsuda A., Kaneko M.K., Ito H., Amano K., Chiba Y., Narimatsu H., Hirabayashi J. Focused differential glycan analysis with the platform antibody-assisted lectin profiling for glycan-related biomarker verification. Mol. Cell Proteomics 2009, 8:99-108.
228. Hsu K.L., Pilobello K.T., Mahal L.K. Analyzing the dynamic bacterial glycome with a lectin microarray approach. Nat. Chem. Biol. 2006, 2:153-157.
229. Pilobello K.T., Slawek D.E., Mahal L.K. Proc. Natl. Acad. Sci. U.S.A. A ratiometric lectin microarray approach to analysis of the dynamic mammalian glycome 2007, 104:11534-11539.
230. Krishnamoorthy L., Bess J.W., Preston A.B., Nagashima K., Mahal L.K. HIV-1 and microvesicles from T cells share a common glycome, arguing for a common origin. Nat. Chem. Biol. 2009, 5:244-250.
231. Matsuda A., Kuno A., Ishida H., Kawamoto T., Shoda J., Hirabayashi J. Development of an all-in-one technology for glycan profiling targeting formalin-embedded tissue sections. Biochem. Biophys. Res. Commun. 2008, 370:259-263.
232. Bochner B.S., Alvarez R.A., Mehta P., Bovin N.V., Blixt O., White J.R., Schnaar R.L. Glycan array screening reveals a candidate ligand for Siglec-8. J. Biol. Chem. 2005, 280:4307-4312.
233. Tateno H., Nakamura-Tsuruta S., Hirabayashi J. Frontal affinity chromatography: sugar-protein interactions. Nat. Protoc. 2007, 2:2529-2537.
234. Zheng T., Peelen D., Smith L.M. Lectin arrays for profiling cell surface carbohydrate expression. J. Am. Chem. Soc. 2005, 127:9982-9983.
235. Chen S., Zheng T., Shortreed M.R., Alexander C., Smith L.M. Analysis of cell surface carbohydrate expression patterns in normal and tumorigenic human breast cell lines using lectin arrays. Anal. Chem. 2007, 79:5698-5702.
236. Tateno H., Uchiyama N., Kuno A., Togayachi A., Sato T., Narimatsu H., Hirabayashi J. A novel strategy for mammalian cell surface glycome profiling using lectin microarray. Glycobiology 2007, 17:1138-1146.
237. Patwa T.H., Zhao J., Anderson M.A., Simeone D.M., Lubman D.M. Screening of glycosylation patterns in serum using natural glycoprotein microarrays and multi-lectin fluorescence detection. Anal. Chem. 2006, 78:6411-6421.
238. Patwa T.H., Wang Y., Miller F.R., Goodison S., Pennathur S., Barder T.J., Lubman D.M. A novel phosphoprotein analysis scheme for assessing changes in premalignant and malignant breast cell lines using 2D liquid separations, protein microarrays and tandem mass spectrometry. Proteomics Clin. Appl. 2008, 3:51-66.
239. Li C., Simeone D.M., Brenner D.E., Anderson M.A., Shedden K.A., Ruffin M.T., Lubman D.M. Pancreatic cancer serum detection using a lectin/glyco-antibody array method. J. Proteome Res. 2009, 8:483-492.
240. Wuhrer M., Catalina M.I., Deelder A.M., Hokke C.H. Glycoproteomics based on tandem mass spectrometry of glycopeptides. J. Chromatogr. B Analyt. Technol. Biomed. Life. Sci. 2007, 849:115-128.
241. Tang J., Liu Y., Yin P., Yao G., Yan G., Deng C., Zhang X. Concanavalin A-immobilized magnetic nanoparticles for selective enrichment of glycoproteins and application to glycoproteomics in hepatocelluar carcinoma cell line. Proteomics 2010, 10:2000-2014.
242. Wang L., Li F., Sun W., Wu S., Wang X., Zhang L., Zheng D., Wang J., Gao Y. Concanavalin A-captured glycoproteins in healthy human urine. Mol. Cell Proteomics 2006, 5:560-562.
243. Wang Y., Wu S.L., Hancock W.S. Approaches to the study of N-linked glycoproteins in human plasma using lectin affinity chromatography and nano-HPLC coupled to electrospray linear ion trap--Fourier transform mass spectrometry. Glycobiology 2006, 16:514-523.
244. Durham M., Regnier F.E. Targeted glycoproteomics: serial lectin affinity chromatography in the selection of O-glycosylation sites on proteins from the human blood proteome. J. Chromatogr. A 2006, 1132:165-173.
245. Takahashi K., Hiki Y., Odani H., Shimozato S., Iwase H., Sugiyama S., Usuda N. Structural analyses of O-glycan sugar chains on IgA1 hinge region using SELDI-TOFMS with various lectins. Biochem. Biophys. Res. Commun. 2006, 350:580-587.
246. Gastaldi D., Paradisi L., Baiocchi C., Medana C., Lo Duca G., Sena L.M., Roccatello D. Mass spectrometry analysis of IgA1 hinge region in patients with IgA nephropathy. J. Nephrol. 2007, 20:689-695.
247. Yang Z., Hancock W.S. Monitoring glycosylation pattern changes of glycoproteins using multi-lectin affinity chromatography. J. Chromatogr. A 2005, 1070:57-64.
248. Qiu R., Regnier F.E. Comparative glycoproteomics of N-linked complex-type glycoforms containing sialic acid in human serum. Anal. Chem. 2005, 77:7225-7231.
249. Alvarez-Manilla G., Atwood J., Guo Y., Warren N.L., Orlando R., Pierce M. Tools for glycoproteomic analysis: size exclusion chromatography facilitates identification of tryptic glycopeptides with N-linked glycosylation sites. J. Proteome Res. 2006, 5:701-708.
250. Wada Y., Tajiri M., Yoshida S. Hydrophilic affinity isolation and MALDI multiple-stage tandem mass spectrometry of glycopeptides for glycoproteomics. Anal. Chem. 2004, 76:6560-6565.
251. Tajiri M., Yoshida S., Wada Y. Differential analysis of site-specific glycans on plasma and cellular fibronectins: application of a hydrophilic affinity method for glycopeptide enrichment. Glycobiology 2005, 15:1332-1340.
252. Wada Y., Tajiri M., Ohshima S. Quantitation of saccharide compositions of O-glycans by mass spectrometry of glycopeptides and its application to rheumatoid arthritis. J. Proteome Res. 2010, 9:1367-1373.
253. Wohlgemuth J., Karas M., Eichhorn T., Hendriks R., Andrecht S. Quantitative site-specific analysis of protein glycosylation by LC-MS using different glycopeptide-enrichment strategies. Anal. Biochem. 2009, 395:178-188.
254. Kurogochi M., Amano M., Fumoto M., Takimoto A., Kondo H., Nishimura S. Reverse glycoblotting allows rapid-enrichment glycoproteomics of biopharmaceuticals and disease-related biomarkers. Angew. Chem. Int. Ed. Engl. 2007, 46:8808-8813.
255. Nishimura S., Niikura K., Kurogochi M., Matsushita T., Fumoto M., Hinou H., Kamitani R., Nakagawa H., Deguchi K., Miura N., Monde K., Kondo H. High-throughput protein glycomics: combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry. Angew. Chem. Int. Ed. Engl. 2004, 44:91-96.
256. von der Lieth C.W., Lutteke T., Frank M. The role of informatics in glycobiology research with special emphasis on automatic interpretation of MS spectra. Biochim. Biophys. Acta 2006, 1760:568-577.
257. von der Lieth C.W., Bohne-Lang A., Lohmann K.K., Frank M. Bioinformatics for glycomics: status, methods, requirements and perspectives. Brief. Bioinform. 2004, 5:164-178.
258. Aoki-Kinoshita K.F. An introduction to bioinformatics for glycomics research. PLoS Comput. Biol. 2008, 4. e1000075.
259. Doubet S., Bock K., Smith D., Darvill A., Albersheim P. The Complex Carbohydrate Structure Database. Trends Biochem. Sci. 1989, 14:475-477.
260. Doubet S., Albersheim P. CarbBank. Glycobiology 1992, 2:505.
261. Aoki K.F., Yamaguchi A., Ueda N., Akutsu T., Mamitsuka H., Goto S., Kanehisa M. KCaM (KEGG Carbohydrate Matcher): a software tool for analyzing the structures of carbohydrate sugar chains. Nucleic Acids Res. 2004, 32:W267-W272.
262. Raman R., Venkataraman M., Ramakrishnan S., Lang W., Raguram S., Sasisekharan R. Advancing glycomics: implementation strategies at the consortium for functional glycomics. Glycobiology 2006, 16:82R-90R.
263. Lutteke T., Bohne-Lang A., Loss A., Goetz T., Frank M., von der Lieth C.W. GLYCOSCIENCES.de: an Internet portal to support glycomics and glycobiology research. Glycobiology 2006, 16:71R-81R.
264. Toukach P., Joshi H.J., Ranzinger R., Knirel Y., von der Lieth C.W. Sharing of worldwide distributed carbohydrate-related digital resources: online connection of the Bacterial Carbohydrate Structure DataBase and GLYCOSCIENCES.de. Nucleic Acids Res. 2007, 35:D280-D286.
265. Herget S., Ranzinger R., Maass K., Lieth C.W. GlycoCT-a unifying sequence format for carbohydrates. Carbohydr. Res. 2008, 343:2162-2171.
266. Maass K., Ranzinger R., Geyer H., von der Lieth C.W., Geyer R. " Glyco-peakfinder" -de novo composition analysis of glycoconjugates. Proteomics 2007, 7:4435-4444.
267. Ceroni A., Maass K., Geyer H., Geyer R., Dell A., Haslam S.M. GlycoWorkbench: a tool for the computer-assisted annotation of mass spectra of glycans. J. Proteome Res. 2008, 7:1650-1659.
268. Ranzinger R., Herget S., Wetter T., von der Lieth C.W. GlycomeDB - integration of open-access carbohydrate structure databases. BMC Bioinformatics 2008, 9:384.
269. Ranzinger R., Frank M., von der Lieth C.W., Herget S. Glycome-DB.org: a portal for querying across the digital world of carbohydrate sequences. Glycobiology 2009, 19:1563-1567.
270. Sahoo S.S., Thomas C., Sheth A., Henson C., York W.S. GLYDE-an expressive XML standard for the representation of glycan structure. Carbohydr. Res. 2005, 340:2802-2807.
271. Packer N.H., von der Lieth C.W., Aoki-Kinoshita K.F., Lebrilla C.B., Paulson J.C., Raman R., Rudd P., Sasisekharan R., Taniguchi N., York W.S. Frontiers in glycomics: bioinformatics and biomarkers in disease. An NIH white paper prepared from discussions by the focus groups at a workshop on the NIH campus, Bethesda MD (September 11-13, 2006). Proteomics 2008, 8:8-20.
272. Loss A., Stenutz R., Schwarzer E., von der Lieth C.W. GlyNest and CASPER: two independent approaches to estimate 1H and 13C NMR shifts of glycans available through a common web-interface. Nucleic Acids Res. 2006, 34:W733-W737.
273. Lutteke T., Frank M., von der Lieth C.W. Carbohydrate Structure Suite (CSS): analysis of carbohydrate 3D structures derived from the PDB. Nucleic Acids Res. 2005, 33:D242-D246.
274. Hansen J.E., Lund O., Tolstrup N., Gooley A.A., Williams K.L., Brunak S. NetOglyc: prediction of mucin type O-glycosylation sites based on sequence context and surface accessibility. Glycoconj. J. 1998, 15:115-130.
275. Julenius K., Molgaard A., Gupta R., Brunak S. Prediction, conservation analysis, and structural characterization of mammalian mucin-type O-glycosylation sites. Glycobiology 2005, 15:153-164.
276. Gupta R., Brunak S. Prediction of glycosylation across the human proteome and the correlation to protein function. Pac. Symp. Biocomput. 2002, 310-322.
277. Bohne-Lang A., von der Lieth C.W. GlyProt: in silico glycosylation of proteins. Nucleic Acids Res. 2005, 33:W214-W219.
278. Cooper C.A., Gasteiger E., Packer N.H. GlycoMod-a software tool for determining glycosylation compositions from mass spectrometric data. Proteomics 2001, 1:340-349.
279. Cooper C.A., Harrison M.J., Wilkins M.R., Packer N.H. GlycoSuiteDB: a new curated relational database of glycoprotein glycan structures and their biological sources. Nucleic Acids Res. 2001, 29:332-335.
280. Cooper C.A., Joshi H.J., Harrison M.J., Wilkins M.R., Packer N.H. GlycoSuiteDB: a curated relational database of glycoprotein glycan structures and their biological sources. 2003 update. Nucleic Acids Res. 2003, 31:511-513.
281. Goldberg D., Sutton-Smith M., Paulson J., Dell A. Automatic annotation of matrix-assisted laser desorption/ionization N-glycan spectra. Proteomics 2005, 5:865-875.
282. Tissot B., Ceroni A., Powell A.K., Morris H.R., Yates E.A., Turnbull J.E., Gallagher J.T., Dell A., Haslam S.M. Software tool for the structural determination of glycosaminoglycans by mass spectrometry. Anal. Chem. 2008, 80:9204-9212.
283. Lohmann K.K., von der Lieth C.W. GLYCO-FRAGMENT: a web tool to support the interpretation of mass spectra of complex carbohydrates. Proteomics 2003, 3:2028-2035.
284. Go E.P., Rebecchi K.R., Dalpathado D.S., Bandu M.L., Zhang Y., Desaire H., GlycoPep DB: a tool for glycopeptide analysis using a " Smart Search" Anal. Chem. 2007, 79:1708-1713.