Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid

Sandro Sonnino, Domenico Acquotti, Laura Cantu', Vanna Chigorno, Manuela Valsecchi, Riccardo Casellato, Massimo Masserini, Mario Corti, Piero Allevi, Guido Tettamanti

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Abstract

GM1 ganglioside containing a hydroxylated fatty acid moiety, GM1(OH), was synthesized starting from lyso-GM1 and d-(+)-2-hydroxystearic acid. The aggregative, geometrical and distribution properties of GM1(OH) were compared with those of stearic acid containing GM1 ganglioside; laser light scattering measurements, differential scanning calorimetry and fluorescence spectroscopy were used. GM1 and GM1(OH) are present in solution as micelles with a hydrodynamic radius of 58.7 and 60.0 Å, and molecular mass of 470 and 570 kDa, respectively. The surface area occupied by the monomer of GM1(OH) at the lipid-water interface of the aggregate was calculated to be 117 Å 2, which is 3 Å 2 lower than that determined for GM1. Proton NMR analyses of GM1 and GM1(OH) suggest different three-dimensional structures at the ganglioside lipid-water interface. Both GM1(OH) and GM1 inserted into dipalmitoylphosphatidylcholine (DPPC) vesicles undergo segregation phenomena, with the formation of ganglioside-enriched microdomains, but GM1(OH) shows a higher degree of dispersion in the DPPC matrix and exerts a lower rigidifying effect than does GM1.

Original languageEnglish
Pages (from-to)95-104
Number of pages10
JournalChemistry and Physics of Lipids
Volume69
Issue number2
DOIs
Publication statusPublished - 1994

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Keywords

  • Ganglioside aggregates
  • Gangliosides
  • Hydroxy fatty acid

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Cite this

Sonnino, S., Acquotti, D., Cantu', L., Chigorno, V., Valsecchi, M., Casellato, R., Masserini, M., Corti, M., Allevi, P., & Tettamanti, G. (1994). Synthesis and aggregative properties of GM1 ganglioside (IV3Neu5AcGgOse4Cer) containing d-(+)-2-hydroxystearic acid. Chemistry and Physics of Lipids, 69(2), 95-104. https://doi.org/10.1016/0009-3084(94)90031-0