Download PDF

On the use of DHB/aniline and DHB/N,N-dimethylaniline matrices for improved detection of carbohydrates: Automated identification of oligosaccharides and quantitative analysis of sialylated glycans by MALDI-TOF mass spectrometry

  • Sergei I. Snovida
  • Justin M. Rak-Banville
  • Hélène Perreault
Articles
First Online:
Received:
Revised:
Accepted:

Abstract

This study demonstrates the application of 2,5-dihydrohybenzoic acid/aniline (DHB/An) and 2,5-dihydroxybenzoic acid/N,N-dimethylaniline (DHB/DMA) matrices for automated identification and quantitative analysis of native oligosaccharides by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS). Both matrices are shown to be superior to pure DHB for native glycans in terms of signal intensities of analytes and homogeneity of sample distribution throughout the crystal layer. On-target formation of stable aniline Schiff base derivatives of glycans in DHB/An and the complete absence of such products in the mass spectra acquired in DHB/DMA matrix provide a platform for automated identification of reducing oligosaccharides in the MALDI mass spectra of complex samples. The study also shows how enhanced sensitivity is achieved with the use of these matrices and how the homogeneity of deposited sample material may be exploited for quick and accurate quantitative analysis of native glycan mixtures containing neutral and sialylated oligosaccharides in the low-nanogram to mid-picogram range.

Keywords

Oligosaccharide Schiff Base Sialic Acid Reflector Mode Sialic Acid Residue 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
Download to read the full article text

References

  1. 1.
    Ohtsubo, K.; Marth, J. D. Glycosylation in Cellular Mechanisms of Health and Disease. Cell. 2006, 126, 855–867.CrossRefGoogle Scholar
  2. 2.
    Eklund, R. A.; Freeze, H. H. Essentials of Glycosylation. Semin. Pediatr. Neurol. 2005, 12, 134–143.CrossRefGoogle Scholar
  3. 3.
    Varki, A. Nothing in Glycobiology Makes Sense, Except in the Light of Evolution. Cell. 2006, 126, 841–845.CrossRefGoogle Scholar
  4. 4.
    Wyss, D. F.; Wagner, G. The Structural Role of Sugars in Glycoproteins. Curr. Opin. Biotechnol. 1996, 7, 409–416.CrossRefGoogle Scholar
  5. 5.
    Schmidt, M. A.; Riley, L. W.; Benz, I. Sweet New World: Glycoproteins in Bacterial Pathogens. Trends Microbiol. 2003, 11, 554–561.CrossRefGoogle Scholar
  6. 6.
    Vigerust, D. J.; Shepherd, V. L. Virus Glycosylation: Role in Virulence and Immune Interactions. Trends Microbiol. 2007, 15, 211–218.CrossRefGoogle Scholar
  7. 7.
    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.CrossRefGoogle Scholar
  8. 8.
    Freeze, H. H. Genetic Defects in the Human Glycome. Nat. Rev. Genet. 2006, 7, 537–551.CrossRefGoogle Scholar
  9. 9.
    Harvey, D. J. Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry of Carbohydrates. Mass Spectrom. Rev. 1999, 18, 349–450.CrossRefGoogle Scholar
  10. 10.
    Zaia, J. Mass Spectrometry of Oligosaccharides. Mass Spectrom. Rev. 2004, 23, 161–227.CrossRefGoogle Scholar
  11. 11.
    Karas, M.; Bachmann, D.; Hillenkamp, F. Influence of the Wavelength in High-Irradiance Ultraviolet Laser Desorption Mass Spectrometry of Organic Molecules. Anal. Chem. 1985, 57, 2935–2939.CrossRefGoogle Scholar
  12. 12.
    Karas, M.; Hillenkamp, F. Laser Desorption Ionization of Proteins with Molecular Masses Exceeding 10,000 Daltons. Anal. Chem. 1988, 60, 2299–2301.CrossRefGoogle Scholar
  13. 13.
    Krüger, R.; Pfenninger, A.; Fournier, I.; Glülckmann, M.; Karas, M. Analyte Incorporation and Ionization in Matrix-Assisted Laser Desorption/Ionization Visualized by pH Indicator Molecular Probes. Anal. Chem. 2001, 73, 5812–5821.CrossRefGoogle Scholar
  14. 14.
    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.CrossRefGoogle Scholar
  15. 15.
    Lattová, E.; Snovida, S.; Perreault, H.; Krokhin, O. Influence of Labeling Group on Ionization and Fragmentation of Carbohydrates in Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2005, 16, 683–696.CrossRefGoogle Scholar
  16. 16.
    Delaney, J.; Vouros, P. Liquid Chromatography Ion Trap Mass Spectrometric Analysis of Oligosaccharides Using Permethylated Derivatives. Rapid Commun. Mass Spectrom. 2001, 15, 325–334.CrossRefGoogle Scholar
  17. 17.
    Snovida, S. I.; Chen, V. C.; Perreault, H. Use of a 2,5-Dihydroxybenzoic Acid/Aniline MALDI Matrix for Improved Detection and On-Target Derivatization of Glycans: A Preliminary Report. Anal. Chem. 2006, 78, 8561–8568.CrossRefGoogle Scholar
  18. 18.
    Snovida, S. I.; Perreault, H. A 2,5-Dihydroxybenzoic Acid/N,N-Dimethylaniline Matrix for the Analysis of Oligosaccharides by Matrix-Assisted Laser Desorption Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 3711–3715.CrossRefGoogle Scholar
  19. 19.
    Snovida, S. I.; Perreault, H. Corrigendum: A 2,5-Dihydroxybenzoic Acid/N,N-Dimethylaniline Matrix for the Analysis of Oligosaccharides by Matrix-Assisted Laser Desorption Ionization Mass Spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 4162.CrossRefGoogle Scholar
  20. 20.
    Snovida, S. I.; Chen, V. C.; Krokhin, O.; Perreault, H. Isolation and Identification of Sialylated Glycopeptides from Bovine alpha1-Acid Glycoprotein by Off-Line Capillary Electrophoresis MALDI-TOF Mass Spectrometry. Anal. Chem. 2006, 78, 6556–6563.CrossRefGoogle Scholar
  21. 21.
    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.CrossRefGoogle Scholar
  22. 22.
    Li, Y. L.; Gross, M. L. Ionic-Liquid Matrices for Quantitative Analysis by MALDI-TOF Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2004, 15, 1833–1837.CrossRefGoogle Scholar
  23. 23.
    Mank, M.; Stahl, B.; Boehm, G. 2,5-Dihydroxybenzoic Acid Butylamine and Other Ionic Liquid Matrixes for Enhanced MALDI-MS Analysis of Biomolecules. Anal. Chem. 2004, 76, 2938–2950.CrossRefGoogle Scholar
  24. 24.
    Sekiya, S.; Wada, Y.; Tanaka, K. Derivatization for Stabilizing Sialic Acids in MALDI-MS. Anal. Chem. 2005, 77, 4962–4968.CrossRefGoogle Scholar
  25. 25.
    Wheeler, S. F.; Harvey, D. J. Negative Ion Mass Spectrometry of Sialylated Carbohydrates: Discrimination of N-Acetylneuraminic Acid Linkages by MALDI-TOF and ESI-TOF Mass Spectrometry. Anal. Chem. 2000, 72, 5027–5039.CrossRefGoogle Scholar

Copyright information

© American Society for Mass Spectrometry 2008

Authors and Affiliations

  • Sergei I. Snovida
    • 1
  • Justin M. Rak-Banville
    • 1
  • Hélène Perreault
    • 1
  1. 1.Department of ChemistryUniversity of ManitobaWinnipegCanada

Personalised recommendations