Skip to main content
NCBI home page
Biochemical Journal logoLink to Biochemical Journal
. 1980 Sep 1;189(3):435–440. doi: 10.1042/bj1890435

Configuration and interactions of the polar head group in gangliosides

Bruno Maggio 1, Federico A Cumar 1, Ranwel Caputto 1
PMCID: PMC1162021  PMID: 7213337

Abstract

1. The interactions of gangliosides with Ca2+ and some polar-head-group requirements for establishment of particular interactions with phosphatidylcholine were studied in monolayers at the air/145mm-NaCl interface. 2. Ganglioside–Ca2+ interactions, as revealed by surface-potential measurements, depended on the position occupied by sialosyl residues in the oligosaccharide chain. The interactions with Ca2+ of the single sialosyl residue of monosialogangliosides occurred above 0.1mm-CaCl2, whereas the interaction of the cation with additional sialosyl groups in di- or tri-sialogangliosides depended on the carbohydrate residue to which the sialosyl moiety was attached. The sialosyl residue bound in sialosyl–sialosyl linkage interacted very little with Ca2+. The sialosyl residue attached to the terminal galactose of the neutral tetrasaccharide chain interacted with Ca2+ above 1μm-CaCl2. 3. Experiments with mixed monolayers containing dihexadecyl phosphate and hexadecyltrimethylammonium indicated that for the occurrence of interactions of polysialogangliosides with phosphatidylcholine characterized by reductions in molecular packing and surface potential both charged groups of the phospholipid and sialosyl residues with particular dipolar properties in the ganglioside are participating. 4. Possible configurations that can explain the behaviour in monolayers were inspected with space-filling molecular models. The position of the carboxylate group of sialosyl residues with respect to the interface and to the sialosyl molecular plane can explain the different orientation of the dipole-moment vector of this residue, which depends on the position to which it is linked in the oligosaccharide chain. Favoured interactions of polysialogangliosides with phosphatidylcholine may result from a configuration allowing a partial matching of two oppositely oriented electrical vectors contributed by the zwitterionic phosphocholine group and particular sialosyl groups.

Full text

PDF
435

Images in this article

438-1PLATE 1
on p.438-1

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Cumar F. A., Maggio B., Caputto R. Dopamine release from nerve endings induced by polysialogangliosides. Biochem Biophys Res Commun. 1978 Sep 14;84(1):65–69. doi: 10.1016/0006-291x(78)90263-2. [DOI] [PubMed] [Google Scholar]
  2. Cumar F. A., Maggio B., Caputto R. Neurotransmitter movements in nerve endings. Influence of substances that modify the interfacial potential. Biochim Biophys Acta. 1980 Mar 27;597(1):174–182. doi: 10.1016/0005-2736(80)90161-3. [DOI] [PubMed] [Google Scholar]
  3. Gally H. U., Niederberger W., Seelig J. Conformation and motion of the choline head group in bilayers of dipalmitoyl-3-sn-phosphatidylcholine. Biochemistry. 1975 Aug 12;14(16):3647–3652. doi: 10.1021/bi00687a021. [DOI] [PubMed] [Google Scholar]
  4. Jaques L. W., Brown E. B., Barrett J. M., Brey WS Jr Weltner W., Jr Sialic acid. A calcium-binding carbohydrate. J Biol Chem. 1977 Jul 10;252(13):4533–4538. [PubMed] [Google Scholar]
  5. Maggio B., Cumar F. A., Caputto R. Induction of membrane fusion by polysialogangliosides. FEBS Lett. 1978 Jun 1;90(1):149–152. doi: 10.1016/0014-5793(78)80318-4. [DOI] [PubMed] [Google Scholar]
  6. Maggio B., Cumar F. A., Caputto R. Interactions of gangliosides with phospholipids and glycosphingolipids in mixed monolayers. Biochem J. 1978 Dec 1;175(3):1113–1118. doi: 10.1042/bj1751113. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Maggio B., Cumar F. A., Caputto R. Surface behaviour of gangliosides and related glycosphingolipids. Biochem J. 1978 Jun 1;171(3):559–565. doi: 10.1042/bj1710559. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Maggio B., Diplock A. T., Lucy J. A. Interactions of tocopherols and ubiquinones with monolayers of phospholipids. Biochem J. 1977 Jan 1;161(1):111–121. doi: 10.1042/bj1610111. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Maggio B., Lucy J. A. Polar-group behaviour in mixed monolayers of phospholipids and fusogenic lipids. Biochem J. 1976 May 1;155(2):353–364. doi: 10.1042/bj1550353. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Maggio B., Lucy J. A. Studies on mixed monolayers of phospholipids and fusogenic lipids. Biochem J. 1975 Sep;149(3):597–608. doi: 10.1042/bj1490597. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Pascher I. Molecular arrangements in sphingolipids. Conformation and hydrogen bonding of ceramide and their implication on membrane stability and permeability. Biochim Biophys Acta. 1976 Dec 2;455(2):433–451. doi: 10.1016/0005-2736(76)90316-3. [DOI] [PubMed] [Google Scholar]
  12. Phillips M. C., Finer E. G., Hauser H. Differences between conformations of lecithin and phosphatidylethanolamine polar groups and their effects on interactions of phospholipid bilayer membranes. Biochim Biophys Acta. 1972 Dec 1;290(1):397–402. doi: 10.1016/0005-2736(72)90084-3. [DOI] [PubMed] [Google Scholar]
  13. SHAH D. O., SCHULMAN J. H. BINDING OF METAL IONS TO MONOLAYERS OF LECITHINS, PLASMALOGEN, CARDIOLIPIN, AND DICETYL PHOSPHATE. J Lipid Res. 1965 Jul;6:341–349. [PubMed] [Google Scholar]
  14. SVENNERHOLM L. CHROMATOGRAPHIC SEPARATION OF HUMAN BRAIN GANGLIOSIDES. J Neurochem. 1963 Sep;10:613–623. doi: 10.1111/j.1471-4159.1963.tb08933.x. [DOI] [PubMed] [Google Scholar]
  15. Seelig A., Seelig J. The dynamic structure of fatty acyl chains in a phospholipid bilayer measured by deuterium magnetic resonance. Biochemistry. 1974 Nov 5;13(23):4839–4845. doi: 10.1021/bi00720a024. [DOI] [PubMed] [Google Scholar]
  16. Sillerud L. O., Prestégard J. H., Yu R. K., Schafer D. E., Konigsberg W. H. Assignment of the 13C nuclear magnetic resonance spectrum of aqueous ganglioside GM1 micelles. Biochemistry. 1978 Jun 27;17(13):2619–2628. doi: 10.1021/bi00606a025. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES