Preparation of lyso-GM1 (Il3Neu5AcGgOse4-long chain bases) by a one-pot reaction

S. Sonnino, D. Acquotti, G. Kirschner, A. Uguaglianza, L. Zecca, F. Rubino, G. Tettamanti

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A simple procedure is described for preparing lyso-GM1, a GM1 derivative that lacks the fatty acid moiety, starting from GM1 ganglioside using a one- pot reaction. Ganglioside deacylation was carried out in KOH/propan-1-ol in the absence of oxygen. The yield of lyso-GM1 under optimal conditions (6 h, 90°C, 0.2 N KOH, 1 mM GM1) was 54%. The chemical structure of lyso-GM1 was determined by 1H-NMR and FAB-MS analyses, thus proving that the acetamide groups of galactosamine and sialic acid units were not affected during the deacylation reaction.

Original languageEnglish
Pages (from-to)1221-1226
Number of pages6
JournalJournal of Lipid Research
Volume33
Issue number8
Publication statusPublished - 1992

Fingerprint

G(M1) Ganglioside
Galactosamine
Gangliosides
N-Acetylneuraminic Acid
Fatty Acids
Nuclear magnetic resonance
Oxygen
Derivatives
lysoGM1 ganglioside
acetamide
Proton Magnetic Resonance Spectroscopy

Keywords

  • gangliosides
  • GM1
  • lyso-gangliosides

ASJC Scopus subject areas

  • Endocrinology

Cite this

Sonnino, S., Acquotti, D., Kirschner, G., Uguaglianza, A., Zecca, L., Rubino, F., & Tettamanti, G. (1992). Preparation of lyso-GM1 (Il3Neu5AcGgOse4-long chain bases) by a one-pot reaction. Journal of Lipid Research, 33(8), 1221-1226.

Preparation of lyso-GM1 (Il3Neu5AcGgOse4-long chain bases) by a one-pot reaction. / Sonnino, S.; Acquotti, D.; Kirschner, G.; Uguaglianza, A.; Zecca, L.; Rubino, F.; Tettamanti, G.

In: Journal of Lipid Research, Vol. 33, No. 8, 1992, p. 1221-1226.

Research output: Contribution to journalArticle

Sonnino, S, Acquotti, D, Kirschner, G, Uguaglianza, A, Zecca, L, Rubino, F & Tettamanti, G 1992, 'Preparation of lyso-GM1 (Il3Neu5AcGgOse4-long chain bases) by a one-pot reaction', Journal of Lipid Research, vol. 33, no. 8, pp. 1221-1226.
Sonnino S, Acquotti D, Kirschner G, Uguaglianza A, Zecca L, Rubino F et al. Preparation of lyso-GM1 (Il3Neu5AcGgOse4-long chain bases) by a one-pot reaction. Journal of Lipid Research. 1992;33(8):1221-1226.
Sonnino, S. ; Acquotti, D. ; Kirschner, G. ; Uguaglianza, A. ; Zecca, L. ; Rubino, F. ; Tettamanti, G. / Preparation of lyso-GM1 (Il3Neu5AcGgOse4-long chain bases) by a one-pot reaction. In: Journal of Lipid Research. 1992 ; Vol. 33, No. 8. pp. 1221-1226.
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