Semisynthetic preparation of N-glycolylneuraminic acid containing GM1 ganglioside: chemical characterization, physico-chemical properties and some biochemical features

S. Sonnino, D. Acquotti, G. Fronza, L. Cantù, V. Chigorno, M. Pitto, G. Kirschner, G. Tettamanti

Research output: Contribution to journalArticlepeer-review

Abstract

N-Glycolylneuraminic acid containing GM1, GM1(NeuGc), was prepared by semisynthetic procedure. The procedure makes use of GM1 ganglioside deacetylated at the level of sialic acid residue (deAc-GM1) and of 1,3-dioxalan-2,4-dione. DeAc-GM1 is prepared from GM1 by alkaline hydrolysis in the presence of tetramethylammonium hydroxide and the glycolylating compound by reaction of glycolic acid with phosgene in dioxane, followed by cyclization under vacuum. Mass spectrometric and nuclear magnetic resonance spectroscopy analyses clearly indicated the presence, in the neosynthesized ganglioside of a glycolic group in the sialic acid residue. Laser-light scattering measurements show that GM1(NeuGc) aggregates in aqueous media being present in solution as micelles with a molecular weight of 576,000 and a hydrodynamic radius of 62.4 Å as determined at 25°C. GM1 (NeuGc) promotes neurite outgrowth in N-2a cells to a similar degree as GM1 (NeuAc), but shows different behaviour under treatment with sialidase from Arthrobacter ureafaciens.

Original languageEnglish
Pages (from-to)181-191
Number of pages11
JournalChemistry and Physics of Lipids
Volume46
Issue number3
DOIs
Publication statusPublished - 1988

Keywords

  • ganglioside
  • laser
  • N-glycolylneuraminic acid
  • nuclear magnetic resonance
  • sialidase

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Fingerprint

Dive into the research topics of 'Semisynthetic preparation of N-glycolylneuraminic acid containing GM1 ganglioside: chemical characterization, physico-chemical properties and some biochemical features'. Together they form a unique fingerprint.

Cite this