Abstract
A strategic method with high speed and sensitivity is outlined for the analysis of mucin-type oligosaccharide from the jelly coat of Xenopus laevis. The method relies primarily on mass spectrometric techniques, in this case matrix-assisted laser desorption/ionization Fourier-transform mass spectrometry (MALDI-FTMS) and collision-induced dissociation (CID). Separation with isolation of the oligosaccharides was streamlined to couple well with mass spectrometry allowing the rapid determination of all detectable components from both neutral and anionic species. Partial structures of anionic components, composed primarily of sulfate esters, were obtained with CID. For neutral species, a method that allowed the complete structural determination using mass spectrometry was used. The method builds on the structure of small number of known compounds to determine unknown structures from the same biological source. In this example, a small number of oligosaccharides, elucidated previously by NMR, were used to develop a set of substructural motifs that were characterized by CID. The presence of the motifs in the CID spectra were then used to determine the structures of unknown compounds that were in abundances too small for NMR analysis.
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References
Varki A, Biological roles of oligosaccharides: all the theories are correct, Glycobiology 3, 97–130 (1993).
Hedrick JL, Nishihara T, Structure and function of the extracellular matrix of anuran eggs, J Electron Microsc Tech 17, 319–35 (1991).
Hedrick JL, Hardy DM, In Methods in Cell Biology, Vol. 36. (Academic Press, NY, 1991), pp. 231–47.
Mozingo NM, Hedrick JL, Distribution of lectin binding sites in Xenopus laevis egg jelly, Developmental Bio 210, 428–39 (1999).
Larabell C, Chandler DE, Fertilization changes in the vitelline envelope of echinoderm and amphibian eggs – self-assembly of an extracellular matrix, J Electron Microsc Tech 17, 294–318 (1991).
Katagiri C, Role of oviducal secretions in mediating gamete fusion in anuran amphibians, Zool Sci 4, 1–14 (1987).
Koyota S, Wimalasir SKM, Hoshi M, Structure of the main saccharide chain in the acrosome reaction-inducing substance of the startish, Asterial amurensis, J Biol Chem 272, 10372–6 (1997).
Alves AP, Mulloy B, Diniz JA, Mourao PAS, Sulfated polysaccharides from the egg jelly layer are species-specific inducers of acrosomal reactions in sperms of sea urchins, J Biol Chem 272, 6965–71 (1997).
Hedrick JL, Vo LH, The glycobiology of the acrsome reaction, J Reprod Devel 44 (suppl.), 15 (1998).
Bonnell BS, Smith SG, Hedrick JL, Microscopy of Glycoproteins, Anal Biochem 271, 91–3 (1999).
Plancke Y, Wieruszeski JM, Alonso C, Boilly B, Strecker G, Structure of four acidic oligosaccharides from the jelly coat surrounding the eggs of Xenopus Laevis, Eur J Biochem 231, 434–9 (1995).
Strecker G, Wieruszeski J-M, Plancke Y, Boilly B, Primary structure of 12 neutral oligosaccharide-alditols released from the jelly coats of the anuran Xenopus laevis by reductive betaelimination, Glycobiology 5, 137–46 (1995).
Yang Y, Orlando R, Simplifying the Exoglycosidase Digestion/ MALDI-MS Procedures for Sequencing N-Linked Carbohydrate Side Chains, Anal Chem 68, 570–2 (1996).
Küster B, Naven TJP, Harvey DJ, Rapid approach for sequencing neutral oligosaccharides by exoglysidase digestion and matrixassisted laser desorption/ionization time-of-flight mass spectrometry, J Mass Spectrom 31, 1131–40 (1996).
Dell A, FAB-mass spectrometry of carbohydrates, Adv Carbohydr Chem Biochem 45, 19–72 (1987).
Domon B, Costello CE, A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates, Glycoconjugate J 5, 397–409 (1988).
Harvey DJ, Quantitative aspects of the matrix-assisted laser desorption ionization mass spectrometry of complex oligosaccharides, Rapid Commun Mass Spectrom 7, 614–9 (1993).
Hofmeister GE, Zhou Z, Leary JA, Linkage position determination in lithium-cationized disaccharides: Tandem mass spectrometry and semiempirical calculations, J Am Chem Soc 113, 5964–70 (1991).
Wong AWC, Voss MT, Lebrilla LR, An anion dopant for oligosaccharides in matrix-assisted laser desorption/ionization mass spectrometry, Anal Chem 71, 205–11 (1999).
Cancilla MT, Penn SG, Lebrilla CB, Alkaline degradation of oligosaccharides coupled with matrix-assisted laser desorption/ ionization – Fourier transform mass spectrometry, a new method for sequencing oligosaccharides, Anal Chem 70, 663–72 (1998).
Tseng K, Lindsay LL, Penn SG, Hedrick JL, Lebrilla CB, Characterization of neutral oligosaccharide-alditols from Xenopus laevis jelly coats by matrix assisted laser Desorption Fourier transform mass spectrometry, Anal Biochem 250, 18–28 (1997).
Wong AW, Wang H, Lebrilla CB, Selection of anionic dopant for quantifying desialylation reactions with MALDI-FTMS, Anal Chem 72, 1419–25 (2000).
Cancilla MT, Wong AW, Voss LR, Lebrilla CB, Fragmentation reactions in the mass spectrometry of neutral oligosaccharides, Anal Chem 71, 3206–18 (1999).
Cancilla MT, Penn SG, Carroll JA, Lebrilla CB, Coordination of alkali metals to oligosaccharide dictates fragmentation behavior in matrix-assited laser desorption/ionization Fourier transform mass spectrometry, J Am Chem Soc 118, 6736–45 (1996).
Tseng K, Hedrick JL, Lebrilla CB, The catalog-library approach for the rapid and sensitive structural elucidation of oligosaccharides, Anal Chem 71, 3747–54 (1999).
Xie Y, Tseng K, Hedrick JL, Lebrilla CB, Structural refinement and confirmation of neutral o-lined oligosaccharides by coupling exoglycosidase digestion and MALDI-FTMS, J Am Soc Mass Spectrom 12, 877–84 (2001).
Guerardel Y, Kol O, Maes E, Lefebvre T, Boilly B, Davril M, Strecker G, O-Glycan variability of egg-jelly mucins from Xenopus laevis: Characterization of four phenotypes that differ by the terminal glycosylation of their mucins, Biochem J 352, 449–63 (2001).
An HJ, Lebrilla CB, Suppression of sialylated by sulfated oligosaccharides in negative MALDI-FTMS, Israel J Chem, in press (2001).
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Tseng, K., Xie, Y., Seeley, J. et al. Profiling with structural elucidation of the neutral and anionic O-linked oligosaccharides in the egg jelly coat of Xenopus laevis by Fourier transform mass spectrometry. Glycoconj J 18, 309–320 (2001). https://doi.org/10.1023/A:1013665031668
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DOI: https://doi.org/10.1023/A:1013665031668