Matrix-Assisted Laser Desorption/Ionization Mass Spectrometric Analysis of Polysulfated-Derived Oligosaccharides Using Pyrenemethylguanidine

Journal of the American Society for Mass Spectrometry

Volumn 20, Issue 1, 2009, Pages 131-137

  Ohara, Keiichiro ^a   Jacquinet, Jean Claude ^b   Jouanneau, Diane ^c   Helbert, William ^c   Smietana, Michael ^a   Vasseur, Jean Jacques ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITÉ D'ORLÉANS   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; CARBOHYDRATES; DESORPTION; IONIZATION; MASS SPECTROMETERS; MASS SPECTROMETRY; OLIGOMERS; OLIGOSACCHARIDES; ORGANIC COMPOUNDS; POLYMERS; SPECTROMETRY;

ANALYTE; CARRAGEENAN; CARRAGEENANS; CHONDROITIN; COMPOSITIONAL INFORMATIONS; IONIZATION EFFICIENCIES; IONIZATION MODES; LASER DESORPTION/IONIZATION; RAPID DETERMINATIONS; SOFTWARE TOOLS; STRUCTURAL DIVERSITIES; STRUCTURAL ELUCIDATIONS; STRUCTURAL INFORMATIONS; SULFATE GROUPS;

STRUCTURAL ANALYSIS;

CARRAGEENAN; CHONDROITIN SULFATE; GUANIDINE DERIVATIVE; OLIGOSACCHARIDE; PYRENEMETHYLGUANIDINE; SUCRALFATE; UNCLASSIFIED DRUG;

ARTICLE; MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION MASS SPECTROMETRY; PROTEIN ANALYSIS; PROTEIN STRUCTURE; SULFATION;

ALGAE; CARRAGEENAN; CHONDROITIN SULFATES; METHYLGUANIDINE; OLIGOSACCHARIDES; PYRENES; SOFTWARE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SUCROSE; SULFATES;

EID: 57749201601     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2008.09.004     Document Type: Article

References (29)

1. Esko J.D., and Selleck S.B. Order Out of Chaos: Assembly of Ligand Binding Sites in Heparan Sulfate. Annu. Rev. Biochem. 71 (2002) 435-471
2. Linhardt R.J., and Toida T. Role of Glycosaminoglycans in Cellular Communication. Acc. Chem. Res. 37 (2004) 431-438
3. Capila I., and Linhardt R.J. Heparin-Protein Interactions. Angew. Chem. Int. Ed. Engl. 41 (2002) 391-412
4. Lopin C., and Jacquinet J.C. From Polymer to Size-defined Oligomers: An Expeditious Route for the Preparation of Chondroitin Oligosaccharides. Angew. Chem. Int. Ed. Engl. 45 (2006) 2574-2578
5. van de Velde F., Peppelman H.A., Rollema H.S., and Tromp R.H. On the Structure of kappa/iota-Hybrid Carrageenans. Carbohydr. Res. 331 (2001) 271-283
6. Menard R., de Ruffray P., Fritig B., Yvin J.C., and Kauffmann S. Defense and Resistance-inducing Activities in Tobacco of the Sulfated beta-1,3 Glucan PS3 and Its Synergistic Activities with the Unsulfated Molecule. Plant Cell Physiol. 46 (2005) 1964-1972
7. McReynolds K.D., and Gervay-Hague J. Chemotherapeutic Interventions Targeting HIV Interactions with Host-associated Carbohydrates. Chem. Rev. 107 (2007) 1533-1552
8. van de Velde F., Knutsen S.H., Usov A.I., Rollema H.S., and Cerezo A.S. H-1 and C-13 High Resolution NMR Spectroscopy of Carrageenans: Application in Research and Industry. Trends Food Sci. Technol. 13 (2002) 73-92
9. Chi L., Amster J., and Linhardt R.J. Mass Spectrometry for the Analysis of Highly Charged Sulfated Carbohydrates. Curr. Anal. Chem. 1 (2005) 223-240
10. Chai W.G., Luo J., Lim C.K., and Lawson A.M. Characterization of Heparin Oligosaccharide Mixtures as Ammonium Salts Using Electrospray Mass Spectrometry. Anal. Chem. 70 (1998) 2060-2066
11. Gunay N.S., Tadano-Aritomi K., Toida T., Ishizuka I., and Linhardt R.J. Evaluation of Counterions for Electrospray Ionization Mass Spectral Sulfated Analysis of a Highly Sulfated Carbohydrate, Sucrose Octasulfate. Anal. Chem. 75 (2003) 3226-3231
12. Siegel M.M., Tabei K., Kagan M.Z., Vlahov I.R., Hileman R.E., and Linhardt R.J. Polysulfated Carbohydrates Analyzed as Ion-paired Complexes with Basic Peptides and Proteins Using Electrospray Negative Ionization Mass Spectrometry. J. Mass Spectrom. 32 (1997) 760-772
13. Zaia J. Mass Spectrometry of Oligosaccharides. Mass Spectrom. Rev. 23 (2004) 161-227
14. Zaia J., Li X.Q., Chan S.Y., and Costello C.E. Tandem Mass Spectrometric Strategies for Determination of Sulfation Positions and Uronic Acid Epimerization in Chondroitin Sulfate Oligosaccharides. J. Am. Soc. Mass Spectrom. 14 (2003) 1270-1281
15. Juhasz P., and Biemann K. Mass-Spectrometric Molecular-Weight Determination of Highly Acidic Compounds of Biological Significance via Their Complexes with Basic Polypeptides. Proc. Natl. Acad. Sci. U. S. A. 91 (1994) 4333-4337
16. Juhasz P., and Biemann K. Utility of Noncovalent Complexes in the Matrix-Assisted Laser-Desorption Ionization Mass-Spectrometry of Heparin-Derived Oligosaccharides. Carbohydr. Res. 270 (1995) 131-147
17. Venkataraman G., Shriver Z., Raman R., and Sasisekharan R. Sequencing Complex Polysaccharides. Science 286 (1999) 537-542
18. Laremore T.N., Murugesan S., Park T.J., Avci F.Y., Zagorevski D.V., and Linhardt R.J. Matrix-Assisted Laser Desorption/Ionization Mass Spectrometric Analysis of Uncomplexed Highly Sulfated Oligosaccharides Using Ionic Liquid Matrices. Anal. Chem. 78 (2006) 1774-1779
19. Laremore T.N., Zhang F.M., and Linhardt R.J. Ionic Liquid Matrix for Direct UV-MALDI-TOF-MS Analysis of Dermatan Sulfate and Chondroitin Sulfate Oligosaccharides. Anal. Chem. 79 (2007) 1604-1610
20. Tissot B., Gasiunas N., Powell A.K., Ahmed Y., Zhi Z.L., Haslam S.M., Morris H.R., Turnbull J.E., Gallagher J.T., and Dell A. Towards GAG Glycomics: Analysis of Highly Sulfated Heparins by MALDI-TOF Mass Spectrometry. Glycobiology 17 (2007) 972-982
21. Laremore T.N., and Linhardt R.J. Improved Matrix-Assisted Laser Desorption/Ionization Mass Spectrometric Detection of Glycosaminoglycan Disaccharides as Cesium Salts. Rapid Commun. Mass Spectrom. 21 (2007) 1315-1320
22. Ohara K., Smietana M., and Vasseur J.J. Characterization of Specific Noncovalent Complexes between Guanidinium Derivatives and Single-stranded DNA by MALDI. J. Am. Soc. Mass Spectrom. 17 (2006) 283-291
23. Schug K.A., and Lindner W. Noncovalent Binding between Guanidinium and Anionic Groups: Focus on Biological- and Synthetic-based Arginine/Guanidinium Interactions with Phosph[on]ate and Sulf[on]ate Residues. Chem. Rev. 105 (2005) 67-113
24. Karst N., and Jacquinet J.C. Stereocontrolled Total Syntheses of Shark Cartilage Chondroitin Sulfate D-related Tetra- and Hexasaccharide Methyl Glycosides. Eur. J. Org. Chem. 5 (2002) 815-825
25. Guibet M., Boulenguer P., Mazoyer J., Kervarec N., Antonopoulos A., Lafosse M., and Helbert W. Composition and Distribution of Carrabiose Moieties in Hybrid kappa-/iota-Carrageenans Using Carrageenases. Biomacromolecules 9 (2008) 408-415
26. Guibet M., Colin S., Barbeyron T., Genicot S., Kloareg B., Michel G., and Helbert W. Degradation of lambda-Carrageenan by Pseudoalteromonas carrageenovora lambda-Carrageenase: A New Family of Glycoside Hydrolases Unrelated to kappa- and iota-Carrageenases. Biochem. J. 404 (2007) 105-114
27. Guibet M., Kervarec N., Genicot S., Chevolot Y., and Helbert W. Complete Assignment of H-1 and C-13 NMR Spectra of Gigartina skottsbergii lambda-Carrageenan Using Carrabiose Oligosaccharides Prepared by Enzymatic Hydrolysis. Carbohydr. Res. 341 (2006) 1859-1869
28. Ohara K., Smietana M., Restouin A., Mollard S., Borg J.P., Collette Y., and Vasseur J.J. Amine-Guanidine Switch: A Promising Approach to Improve DNA Binding and Antiproliferative Activities. J. Med. Chem. 50 (2007) 6465-6475
29. Salih B., and Zenobi R. MALDI Mass Spectrometry of Dye-Peptide and Dye-Protein Complexes. Anal. Chem. 70 (1998) 1536-1543