Skip to main content
SpringerLink
Log in

Isolation and Analysis of Gangliosides with O-Acetylated Sialic Acids

  • Conference paper
Gangliosides and Modulation of Neuronal Functions

Part of the book series: NATO ASI Series ((ASIH,volume 7))

Abstract

Sialic acids are a group of about 30 closely related sugars derived from neuraminic acid. The most frequently occurring members of this family are N-acetylneuraminic acid (Neu5Ac) > N-glycolylneuraminic acid (Neu5Gc) > N-acetyl-9-0-acetylneuraminic acid (Neu5,9Ac2) > N-glycolyl-9-0-acetylneuraminic acid (Neu9Ac5Gc) > N-acetyl-4-0-acetylneuraminic acid (Neu4,5Ac2). As sialic acids are in most cases linked to the terminal position of carbohydrate chains and are thus the first molecules to be recognized from outside of e.g. a cell, they may influence the interaction of cells with other cells or molecules (see this volume, Schauer & Reuter). Consequently, modification of sialic acids as e.g. 0-acetylation is expected to alter these interaction phenomena and other properties of sialic acids.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Sonnino S, Ghidoni R, Chigorno V, Masserini M, Tettamanti G (1983) Recognition by two-dimensional thin-layer chromatography and densitometric quantification of alkali-labile gangliosides from the brain of different animals. Anal Biochem 128: 104–114

    Article  PubMed  CAS  Google Scholar 

  2. Hakomori S-i, Saito T (1969) Isolation and characterization of a glycosphingolipid having a new sialic acid. Biochemistry 8: 5082–5088

    Article  PubMed  CAS  Google Scholar 

  3. Veh RW, Sander M, Haverkamp J, Schauer R (1979) Demonstration of 0-acetyl groups in ganglioside-bound sialic acids and their effect on the action of bacterial and mammalian neuraminidases. Glycoconj Res (Gregory JD, Jeanloz RW eds) Vol 1, 557–559. Academic Press New York

    Google Scholar 

  4. Ghidoni R, Sonnino S, Tettamanti G, Baumann N, Reuter G, Schauer R (1980) Isolation and characterization of a trisialoganglioside from mouse brain, containing 9-0-acetyl-N-acetylneuraminic acid. J Biol Chem 255: 6990–6995

    PubMed  CAS  Google Scholar 

  5. Chigorno V, Sonnino S, Ghidoni R, Tettamanti G (1982) Isolation and characterization of a tetrasialoganglioside from mouse brain, containing 9-0-acetyl, N-acetylneuraminic acid. Neurochem Int 4: 531–539

    Google Scholar 

  6. Gowda DC, Reuter G, Shukla AK, Schauer R (1984) Identification of a disialoganglioside (GD1a) containing terminal N-acetyl-9-0-acetylneuraminic acid in rat erythrocytes. Hoppe-Seyler’s Z Physiol Chem 365: 1247–1253

    Article  PubMed  CAS  Google Scholar 

  7. Cheresh DA, Varki AP, Varki NM, Stallcup WB, Levine J, Reisfeld RA (1984) A monoclonal antibody recognizes an O-acylated sialic acid in a human melanoma-associated ganglioside. J Biol Chem 259: 7453–7459

    PubMed  CAS  Google Scholar 

  8. Thurin J, Herlyn M, Hindsgaul O, Strömberg N, Karlsson K-A, Elder D, Steplweski Z, Koprowski H (1985) Proton NMR and fast-atom bombardment mass spectrometry analysis of the melanoma-associated ganglioside 9-0-acetyl-GD3. J Biol Chem 260: 14556–14563

    PubMed  CAS  Google Scholar 

  9. Ledeen RW, Yu RK (1982) Gangliosides: Structure, isolation, and analysis. Methods Enzymol 83: 139–191

    Google Scholar 

  10. Kanfer JN, Hakomori S-i (eds) (1983) Sphingolipid Biochemistry, Handbook Lipid Res Vol 3. Plenum Press New York London

    Google Scholar 

  11. Wiegandt H (ed) (1985) Glycolipids, New Comprehensive Biochemistry Vol 10 Elsevier Amsterdam New York London

    Google Scholar 

  12. Gazzotti G, Sonnino S, Ghidoni R (1985) Normal-phase high-performance liquid chromatographic separation of non-derivatized ganglioside mixtures J Chromatogr 348: 371–378

    CAS  Google Scholar 

  13. Mänsson J-E, Rosengren B, Svennerhom L (1985) Separation of gangliosides by anion-exchange chromatography on Mono Q. J Chromatogr 322: 465–472

    Article  PubMed  Google Scholar 

  14. Ando S. Up to date methods and assessments for the isolation and purification of gangliosides. This vol.

    Google Scholar 

  15. Gazzotti G, Sonnino S, Ghidoni R, Orlando P, Tettamanti G (1984) Preparation of the tritiated molecular forms of gangliosides with homogeneous long chain base composition. Glycoconjugate J 1: 111–121

    Article  CAS  Google Scholar 

  16. Sonnino S, Ghidoni R, Gazzotti G, Kirschner G, Galli G, Tettamanti G (1984) High performance liquid chromatography preparation of the molecular species of GM1 and GD1a gangliosides with homogeneous long chain base composition. J Lipid Res 25: 620–629

    PubMed  CAS  Google Scholar 

  17. Ishizuka I, Inomata M, Ueno K, Yamakawa T (1978) Sulfated glyceroglyco- lipids in rat brain. J Biol Chem 253: 898–907

    PubMed  CAS  Google Scholar 

  18. Kochetkov NK, Smirnova GP, Chekareva NV (1976) Isolation and structural studies of a sulfated sialosphingolipid from the sea urchin Echinocardium cordatum. Biochim Biophys Acta 424: 274–283

    PubMed  CAS  Google Scholar 

  19. Slomiany A, Kojima K, Banas-Gruszka Z, Slomiany BL (1981) Structure of a novel sulfated sialoglycosphingolipid from bovine gastric mucosa. Biochem Biophys Res Commun 100: 778–784

    Article  PubMed  CAS  Google Scholar 

  20. Reuter G, Schauer R (1986) Chemical and electron ionization mass spectrometry analysis of sialic acids from the starfish Asterias rubens. In: Abstracts of the XIIIth Int Carbohydrate Symp, Cornell Univ, Ithaca, New York, p 240

    Google Scholar 

  21. Schauer R (1978) Characterization of sialic acids. Methods Enzymol 50: 64–89

    Article  PubMed  CAS  Google Scholar 

  22. Schauer R (1987) Analysis of sialic acids. Methods Enzymol 138: 132–161

    Article  PubMed  CAS  Google Scholar 

  23. Schauer R, Veh RW, Sander M, Corfield AP, Wiegandt H (1980) “Neuraminidase-resistant” sialic acid residues of gangliosides. Adv Exp Med Biol 125:283–294

    Google Scholar 

  24. Corfield AP, Sander-Wewer M, Veh RW, Wember M, Schauer R (1986) The action of sialidases on substrates containing 0-acetyl sialic acids. Biol Chem Hoppe-Seyler 367: 433–439

    Article  PubMed  CAS  Google Scholar 

  25. Svennerholm L (1957) Quantitative estimation of sialic acids. Biochim Biophys Acta 24: 604–611

    Article  PubMed  CAS  Google Scholar 

  26. Shukla AK, Schauer R (1986) Analysis of sialidase and N-acetylneuraminate pyruvate-lyase substrate specificity by high-performance liquid chromatography. Anal Biochem 158: 158–164

    Article  PubMed  CAS  Google Scholar 

  27. Schauer R (1987) Metabolism of 0-acetyl groups of sialic acids. Methods Enzymol 138: 611–626

    Article  PubMed  CAS  Google Scholar 

  28. Reuter G, Schauer R (1986) Comparison of electron and chemical ionization mass spectrometry of sialic acids. Anal Biochem 157: 39–46

    Article  PubMed  CAS  Google Scholar 

  29. Rokukawa C, Kushi Y, Ueno K, Handa S (1982) Structural study on gangliosides from rat liver and erythrocytes. J Biochem 92: 1481–1488

    PubMed  CAS  Google Scholar 

  30. Momoi T, Wiegandt H (1980) Separation and micro-detection of oligosaccharides of glycosphingolipids by high performance cellulose thin-layer chromatography-autoradiofluorography. Hoppe-Seyler1s Z Physiol Chem 361: 1201–1210

    Article  CAS  Google Scholar 

  31. Iwamori M, Shimomura J, Tsuyuhara S, Nagai Y (1984) Gangliosides of various rat tissues: distribution of ganglio-N-tetraose-containing gangliosides and tissue-characteristic composition of gangliosides. J Biochem 95: 761–770

    PubMed  CAS  Google Scholar 

  32. Egge H, Peter-Katalinic J, Reuter G, Schauer R, Ghidoni R, Sonnino S, Tettamanti G (1985) Analysis of gangliosides using fast atom bombardment mass spectrometry. Chem Phys Lipids 37: 127–141

    Article  PubMed  CAS  Google Scholar 

  33. Corfield AP, Schauer R (1982) Occurrence of sialic acids. In: Sialic Acids - Chemistry, Metabolism, and Function (Schauer R, ed) Cell Biol Monogr 10: 5–50

    Google Scholar 

  34. Schauer R (1982) Chemistry, metabolism and biological functions of sialic acids. Adv Carbohydr Chem Biochem 40: 131–234

    Article  PubMed  CAS  Google Scholar 

  35. Rahmann H, Hilbig R, Probst W, Mühleisen M (1984) Brain gangliosides and thermal adaptation in vertebrates. Adv Exp Med Biol 174: 395–404

    PubMed  CAS  Google Scholar 

  36. Varki A, Kornfeld S (1980) An autosomal dominant gene regulates the extent of 9-0-acetylation of murine erythrocyte sialic acids. A probable explanation for the variation in capacity to activate the human alternate complement pathway J Exp Med 152: 532–544

    CAS  Google Scholar 

  37. Herrler G, Rott R, Klenk H-D, Müller H-P, Shukla AK, Schauer R (1985) The receptor-destroying enzyme of influenza C virus is neuraminate-0-acetyl- esterase. Embo J 4: 1503–1506

    PubMed  CAS  Google Scholar 

  38. Shukla AK, Schauer R (1982) Fluorimetric determination of unsubstituted and 9(8)-0-acetylated sialic acids in erythrocyte membranes. Hoppe-SeylerS Z Physiol Chem 363: 255–262

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biochemisches Institut, Christian-Albrechts-Universität, Olshausenstr. 40, D-2300, Kiel, Germany

    G. Reuter & R. Schauer

Authors
  1. G. Reuter
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Schauer
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Zoological Institute, University of Stuttgart-Hohenheim, Garbenstr. 30, 7000, Stuttgart 70, Germany

    Hinrich Rahmann

Rights and permissions

Reprints and permissions

Copyright information

© 1987 Springer-Verlag Berlin Heidelberg

About this paper

Cite this paper

Reuter, G., Schauer, R. (1987). Isolation and Analysis of Gangliosides with O-Acetylated Sialic Acids. In: Rahmann, H. (eds) Gangliosides and Modulation of Neuronal Functions. NATO ASI Series, vol 7. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-71932-5_10

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-71932-5_10

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-71934-9

  • Online ISBN: 978-3-642-71932-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation