A relative and absolute quantification of neutral N-linked oligosaccharides using modification with carboxymethyl trimethylammonium hydrazide and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

Analytical Biochemistry

Volumn 379, Issue 1, 2008, Pages 45-59

  Gil, Geun Cheol ^a   Kim, Yun Gon ^a   Kim, Byung Gee ^a  

^a Seoul National University   (South Korea)

Author keywords

Carboxymethyl trimethylammonium hydrazide; Glycomics; MS; Oligosaccharide; Quantification

Indexed keywords

DESORPTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INDUCTIVELY COUPLED PLASMA; MAMMALS; OLIGOSACCHARIDES; POLYSACCHARIDES; PROTEINS;

ABSOLUTE QUANTIFICATION; CARBOXYMETHYL; GLYCOMICS; HUMAN IMMUNOGLOBULIN G; IONIZATION EFFICIENCY; MATRIX-ASSISTED LASER DESORPTION/IONIZATION-TIME-OF-FLIGHT MASS SPECTROMETRY; NEUTRAL OLIGOSACCHARIDES; QUANTIFICATION;

MASS SPECTROMETRY;

ASPARAGINE LINKED OLIGOSACCHARIDE; CARBOXYMETHYL TRIMETHYLAMMONIUM HYDRAZIDE; CATION; DEXTRAN; GLYCAN DERIVATIVE; HYDRAZIDE DERIVATIVE; IMMUNOGLOBULIN G; MAGNESIUM ION; MEMBRANE PROTEIN; OLIGOSACCHARIDE; OVALBUMIN; POTASSIUM ION; SODIUM ION;

ANIMAL TISSUE; ARTICLE; GLYCOBIOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KIDNEY; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MINIPIG; NONHUMAN; PRIORITY JOURNAL; RELIABILITY; REPRODUCIBILITY; SENSITIVITY ANALYSIS;

SUIDAE;

EID: 45049083308     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2008.04.039     Document Type: Article

References (26)

1. Anumula K.R. Advances in fluorescence derivatization methods for high-performance liquid chromatographic analysis of glycoprotein carbohydrates. Anal. Biochem. 350 (2006) 1-23
2. Karlsson N.G., and Hansson G.C. Analysis of monosaccharide composition of mucin oligosaccharide alditols by high-performance anion-exchange chromatography. Anal. Biochem. 224 (1995) 538-541
3. Wang W.T., Erlansson K., Lindh F., Lundgren T., and Zopf D. High-performance liquid chromatography of sialic acid-containing oligosaccharides and acidic monosaccharides. Anal. Biochem. 190 (1990) 182-187
4. Viseux N., Hronowski X., Delaney J., and Domon B. Qualitative and quantitative analysis of the glycosylation pattern of recombinant proteins. Anal. Chem. 73 (2001) 4755-4762
5. Wuhrer M., Koeleman C.A., Deelder A.M., and Hokke C.H. Normal-phase nanoscale liquid chromatography-mass spectrometry of underivatized oligosaccharides at low-femtomole sensitivity. Anal. Chem. 76 (2004) 833-838
6. Garner B., Harvey D.J., Royle L., Frischmann M., Nigon F., Chapman M.J., and Rudd P.M. Characterization of human apolipoprotein B100 oligosaccharides in LDL subfractions derived from normal and hyperlipidemic plasma: Deficiency of α- N -acetylneuraminyllactosyl ceramide in light and small dense LDL particles. Glycobiology 11 (2001) 791-802
7. Behr J.R., Matsumoto Y., White F.M., and Sasisekharan R. Quantification of isomers from a mixture of twelve heparin and heparan sulfate disaccharides using tandem mass spectrometry. Rapid Commun. Mass Spectrom. 19 (2005) 2553-2562
8. Ninonuevo M.R., Ward R.E., LoCascio R.G., German J.B., Freeman S.L., Barboza M., Mills D.A., and Lebrilla C.B. Methods for the quantitation of human milk oligosaccharides in bacterial fermentation by mass spectrometry. Anal. Biochem. 361 (2007) 15-23
9. Kang P., Mechref Y., Kyselova Z., Goetz J.A., and Novotny M.V. Comparative glycomic mapping through quantitative permethylation and stable-isotope labeling. Anal. Chem. 79 (2007) 6064-6073
10. Kameyama A., Kaneda Y., Yamanaka H., Yoshimine H., Narimatsu H., and Shinohara Y. Detection of oligosaccharides labeled with cyanine dyes using matrix-assisted laser desorption/ionization mass spectrometry. Anal. Chem. 76 (2004) 4537-4542
11. Miura Y., Shinohara Y., Furukawa J., Nagahori N., and Nishimura S. Rapid and simple solid-phase esterification of sialic acid residues for quantitative glycomics by mass spectrometry. Chemistry 13 (2007) 4797-4804
12. Gouw J.W., Burgers P.C., Trikoupis M.A., and Terlouw J.K. Derivatization of small oligosaccharides prior to analysis by matrix-assisted laser desorption/ionization using glycidyltrimethylammonium chloride and Girard′s reagent T. Rapid Commun. Mass Spectrom. 16 (2002) 905-912
13. Naven T.J.P., and Harvey D.J. Cationic derivatization of oligosaccharides with Girard's T reagent for improved performance in matrix-assisted laser desorption/ionization and electrospray mass spectrometry. Rapid Commun. Mass Spectrom. 10 (1996) 829-834
14. Setcavage T.M., and Kim Y.B. Variability of the immunological state of germ-free colostrums-deprived Minnesota miniature piglets. Infect. Immun. 13 (1976) 600-607
15. Kim Y.G., Kim S.Y., Hur Y.M., Joo H.S., Chung J., Lee D.S., Royle L., Rudd P.M., Dwek R.A., Harvey D.J., and Kim B.G. The identification and characterization of xenoantigenic nonhuman carbohydrate sequences in membrane proteins from porcine kidney. Proteomics 6 (2006) 1133-1142
16. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
17. Jefferis R., Lund J., Mizutani H., Nakagawa H., Kawazoe Y., Arata Y., and Takahashi N. A comparative study of the N-linked oligosaccharide structures of human IgG subclass proteins. Biochem. J. 268 (1990) 529-537
18. Krapp S., Mimura Y., Jefferis R., Huber R., and Sondermann P. Structural analysis of human IgG-Fc glycoforms reveals a correlation between glycosylation and structural integrity. J. Mol. Biol. 325 (2003) 979-989
19. Nisbet A.D., Saundry R.H., Moir A.J., Fothergill L.A., and Fothergill J.E. The complete amino-acid sequence of hen ovalbumin. Eur. J. Biochem. 115 (1981) 335-345
20. Suzuki T., Kitajima K., Emori Y., Inoue Y., and Inoue S. Site-specific de- N -glycosylation of diglycosylated ovalbumin in hen oviduct by endogenous peptide: N -Glycanase as a quality control system for newly synthesized proteins. Proc. Natl. Acad. Sci. USA 94 (1997) 6244-6249
21. Y-G. Kim, G-C. Gil, D. J. Harvey, B-G. Kim, Structural analysis of α-Gal and new non-Gal carbohydrate epitopes from specific pathogen-free miniature pig kidney, Proteomics (in press).
22. Cooper D.K., Koren E., and Oriol R. Genetically engineered pigs. Lancet 342 (1993) 682-683
23. Galili U. The α-Gal epitope (Gal α 1-3Gal β 1-4GlcNAc-R) in xenotransplantation. Biochimie 83 (2001) 557-563
24. Good A.H., Cooper D.K., Malcolm A.J., Ippolito R.M., Koren E., Neethling F.A., Ye Y., Zuhdi N., and Lamontagne L.R. Identification of carbohydrate structures that bind human antiporcine antibodies: Implications for discordant xenografting in humans. Transplant Proc. 24 (1992) 559-562
25. Harvey D.J. Quantitative aspects of the matrix-assisted laser desorption mass spectrometry of complex oligosaccharides. Rapid Commun. Mass Spectrom. 7 (1993) 614-619
26. Naven T.J., and Harvey D.J. Effect of structure on the signal strength of oligosaccharides in matrix-assisted laser desorption/ionization mass spectrometry on time-of-flight and magnetic sector instruments. Rapid Commun. Mass Spectrom. 10 (1996) 1361-1366