Advances in Ganglioside Chemistry

  • Sandro Sonnino
  • Domenico Acquotti
  • Günther Kirschner
  • Giovanni Fronza
  • Guido Tettamanti
Part of the FIDIA Research Series book series (FIDIA, volume 6)

Abstract

Gangliosides, sialic acid containing glycosphingolipids, are normal components of the plasma membrane of vertebrate cells and are particularly abundant in the nervous system. They are constituted of a hydrophilic portion, the negatively charged oligosaccharide, and a hydrophobic portion, the ceramide (N-acylated long chain base), linked together by a glycosidic linkage (Ledeen and Yu, 1978; Wiegandt, 1982). The hydrophilic portion is oriented towards the extracellular environment and is assumed to be involved in recognition phenomena mediated by specific interactions between the oligosaccharide moiety and the external ligand (Brady and Fishman, 1979; Holmgren et al., 1980). The hydrophobic portion is inserted into the lipid layer of the membrane and might participate in the process of signal transduction through the membrane (Brady and Fishman, 1979).

Keywords

Sialic Acid Specific Radioactivity Redistilled Water Chain Base Oligosaccharide Moiety 
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.

Abbreviations

Neu

neuraminic acid

l.c.b.

long chain base

DDQ

dicyanodichlorobenzoquinone

DMSO-d6

deuterated dimethylsulfoxide

ESR

electron spin resonance

NMR

nuclear magnetic resonance

EPC

egg phosphatidylcholine

SUV

small unilamellar vesicles

c.m.c.

critical micellar concentration

GLC-MS

gas liquid chromatography-mass spectrometry

FAB-MS

fast atom bombardment-mass spectrometry.

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References

  1. Acquotti D, Sonnino S, Masserini M, Casella L, Fronza G, Tettamanti G (1986) A new chemical procedure for the preparation of gangliosides carrying fluorescent or paramagnetic probes on the lipid moiety. Chem Phys Lipids 40: 71–86.PubMedCrossRefGoogle Scholar
  2. Brady O and Fishman PH (1979) Biotransducers of membrane–mediated information. Adv Enzymol 50: 303–323.PubMedGoogle Scholar
  3. Bertoli E, Masserini M, Sonnino S, Ghidoni R, Cestaro B, Tettamanti G (1981) Electron paramagnetic resonance studies on the fluidity and surface dynamics of egg phosphatidylcholine vesicles containing gangliosides. Biochim Biophys Acta 467: 196–202.Google Scholar
  4. Cantù L, Corti M, Sonnino S, Ghidoni R, Gazzotti G, Tettamanti G (1985) Micellar properties of hydrogenated and natural GM1, in Glycoconjugates, proceedings of the VIII International Symposium, Houston, Texas, U S A, September 8–13, Davidson EA, Williams JC, Ferrante NM eds Praeger, p. 471.Google Scholar
  5. Chigorno V, Sonnino S, Ghidoni R, Tettamanti G (1982) Densitometric quantification of brain gangliosides, separated by two dimensional thin layer chromatography. Neurochem Int 5, 397–403.CrossRefGoogle Scholar
  6. Chigorno V, Pitto M, Cardace G, Acquotti D, Kirschner G, Sonnino S, Ghidoni R, Tettamanti G (1985) Association of gangliosides to fibroblasts in culture: a study performed with GM1 [“C]-labelled at the sialic acid acetyl group. Glycoconjugate J 2, 279–291.CrossRefGoogle Scholar
  7. Corti M, Degiorgio V, Sonnino S, Ghidoni R, Masserini M, iettamanti G (1981) GM1 ganglioside–Triton X-100 mixed micelles: changes of micellar properties studied by laser-light scattering and enzymatic methods. Chem Phys Lipids 28, 197–214.PubMedCrossRefGoogle Scholar
  8. Formisano S, Johnson ML, Lee G, Aloj SM, Edelhoc H (1979) Critical micelle concentrations of gangliosides. Biochemistry 18, 1119–1124.PubMedCrossRefGoogle Scholar
  9. Gazzotti G, Sonnino S, Ghidoni R, Kirschner G, Tettamanti G (1984a) Analytical and preparative high-performance liquid chromatography of gangliosides. J Neurosc Res 12, 179–192.CrossRefGoogle Scholar
  10. Gazzotti G, Sonnino S, Ghidoni R, Orlando P, Tettamanti G (1984b) Preparation of the tritiated molecular forms of gangliosides, separated with homogeneous long chain base composition. Glycoconjugate J, 1, 111–121.CrossRefGoogle Scholar
  11. Gazzotti G, Sonnino S, Ghidoni R (1985) Normal-phase high performance liquid chromatographic separation of non-derivatized ganglioside mixtures. J Chromatogr 348, 371–378.PubMedCrossRefGoogle Scholar
  12. Ghidoni R, Tettamanti G, Zambotti V (1977) Labelling of natural substrates for the radiochemical assay of enzymes involved in the lipid storage diseases: a general procedure for tritiation of gangliosides. Biochem Exp Biol 13, 61–69.PubMedGoogle Scholar
  13. 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-Nacetylneuraminic acid. J Biol Chem 255, 6990–6995.PubMedGoogle Scholar
  14. Ghidoni R, Sonnino S, Masserini M, Orlando P, Tettamanti G (1981) Specific tritium labeling of gangliosides at the 3-position of sphingosines. J Lipid Res 22, 1286–1295.PubMedGoogle Scholar
  15. Gross SK, Williams MA, McCluer RM (1980) Alkali labile, sodium borohydride-reducible ganglioside sialic acid residues in brain. J Neurochem 34, 1351–1361.PubMedCrossRefGoogle Scholar
  16. Holmgren JH, Elwing H, Fredman P, Strannegard O, Svennerholm L (1980) Gangliosides as receptors for bacterial toxins and Sendai virus. Adv Exp Med Biol 125, 453–470.PubMedCrossRefGoogle Scholar
  17. IUPAC-IUB Commission on Biochemical Nomenclature (1977) The nomenclature of lipids. Lipids 12, 455–468.CrossRefGoogle Scholar
  18. Koerner TAW, Prestegard JH, Demou PC, Yu RK (1983) High resolution proton NMR studies of gangliosides. 1. Use of homonuclear two-dimensional spin-echo J.-correlated spectroscopy for determination of residue composition and anomeric configuration. Biochemistry 22, 2676–2687.Google Scholar
  19. Ledeen RW and Yu RK (1978) in Research Methods in Neurochemistry, Marks N and Roonight R eds, Plenum Publishing Corp N Y, 371–410.CrossRefGoogle Scholar
  20. Leskawa KC, Dasgupta S, Chien JL, Hogan EL (1984) A simplified procedure for the preparation of tritiated GM1 ganglioside and other glycosphingolipids. Anal Biochem 140, 172–177. Marsch D (1981) in Electron spin resonance: spin lebels. E Grell ed Membrane spectroscopy, Springer-Verlag, Berlin, 51–142.Google Scholar
  21. Novak A, Lowden JA, Gravel YL, Wolfe LS (1979) Preparation of radiolabeled GM2 and GA2 gangliosides. J Lipid Res 678–681.Google Scholar
  22. Orlando P, Cocciante G, Ippolito G, Massari P, Roberti S, Tettamanti G (1979) The fate of tritium labeled GM1 ganglioside injected in mice. Pharmacol Res Comm 11, 759–773.CrossRefGoogle Scholar
  23. Pascher J (1976) Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability. Biochim Biophys Acta 455, 433–451.PubMedCrossRefGoogle Scholar
  24. Riboni L, Sonnino S, Acquotti D, Malesci A, Ghidoni R, Egge H, Mingrino S, Tettamanti G (1986) Natural occurrence of ganglioside lactones: isolation and characterization of GD1b inner ester from adult human brain. J Biol Chem 261: 8514–8519.PubMedGoogle Scholar
  25. Schraven J, Cap C, Nowoczek G, Sandhoff K (1977) A radiometric assay for sialidase activity on ganglioside GD1a. Anal Biochem 78, 333–339.PubMedCrossRefGoogle Scholar
  26. Schwarzmann (1978) A simple and novel method for tritium labeling of gangliosides and other glycosphingolipids, Biochim Biophys Acta 529, 106–114.PubMedCrossRefGoogle Scholar
  27. Sonnino S, Ghidoni R, Galli G, Tettamanti G (1978) On the structure of a new fucose containing gangliosides from pig cerebellum. J Neurochem 31, 947–956.PubMedCrossRefGoogle Scholar
  28. 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 GDIa gangliosides with homogeneous long chain base composition. J Lipid Res 25, 620–629.PubMedGoogle Scholar
  29. Sonnino S, Kirschner G, Ghidoni R, Acquotti D, Tettamanti G (1985) Preparation of GM1 ganglioside molecular species having homogeneous fatty acid and long chain base moieties. J Lipid Res 26, 248–257.PubMedGoogle Scholar
  30. Suzuki Y and Suzuki K (1972) Specific radioactive labeling of terminal N-acetylgalactosamine of glycosphingolipids by the galactose oxidase-sodium borohydride method. J Lipid Res 13, 687–690.PubMedGoogle Scholar
  31. Svennerholm L (1970) in Handbook of neurochemistry. Vol. III, A Lajtha, ed, Plenum Publishing Corp, New York, 425–452.Google Scholar
  32. Tallman JF, Fishman PH, Henneberry RC (1977) Determination of sialidase activities in HeLa cells using gangliosides specifically labelled in N-acetylneuraminic acid. Arch Biochem Biophys 182, 556–562.PubMedCrossRefGoogle Scholar
  33. Tettamanti G, Bonali F, Marchesini S and Zambotti V (1973) A new procedure for the extraction, purification and fractionation of brain gangliosides. Biochim Biophys Actra 296, 160–170.CrossRefGoogle Scholar
  34. Ulrich-Bott B and Wiegandt H (1984) Micellar properties of glycosphingolipids in aqueous media. J Lipid Res 25, 1233–1245.PubMedGoogle Scholar
  35. Veh RW, Corfield AP, Sander M, Schaver R (1977) Neuraminic acid-specific modification and tritium labelling of gangliosides. Biochim Biophys Acta 486, 145–160.CrossRefGoogle Scholar
  36. Wiegandt H (1982) The gangliosides. Adv Neurochem 4, 149–223.CrossRefGoogle Scholar
  37. Yu RK, Koerner TAW, Ando S, Yome HC, Prestegard JM (1985) High-resolution proton NMR studies of gangliosides. III. Elucidation of the structure of ganglioside GM3 lactone. J Biochem 98, 1367–1373.PubMedGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1986

Authors and Affiliations

  • Sandro Sonnino
    • 1
  • Domenico Acquotti
    • 1
  • Günther Kirschner
    • 2
  • Giovanni Fronza
    • 3
  • Guido Tettamanti
    • 1
  1. 1.Study Center for the Functional Biochemistry of Brain Lipids, Department of Biological Chemistry, The Medical SchoolUniversity of MilanMilanoItaly
  2. 2.Department of ChemistryFIDIA Research LaboratoriesAbano TermeItaly
  3. 3.CNR Study Center for Natural Organic Substances, Department of ChemistryPolytechnic School of MilanMilanoItaly

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