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Ganglioside lactones:1H-NMR determination of the inner ester position of GD1b-ganglioside lactone naturally occurring in human brain or produced by chemical synthesis

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Abstract

The complete definition of the chemical structure of GD1b-ganglioside (GD1b) lactone isolated from human brain has been given by means of spectrometric and spectroscopic analyses. GD1h lactone contains a single ester linkage involving the external sialic acid carboxyl group and the C-9 hydroxyl group of the internal sialic acid unit. A synthetic lactone of GD1b prepared treating GD1b with glacial acetic acid characterized in the same way showed an identical chemical structure.

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Abbreviations

GM1 :

GM1-ganglioside, II3NeuAc-GgOse4Cer, Galβ1-3GalNacβ1-4[NeuAcα2-3]Galβ1-4Glcβ1-1′Cer

GD1b :

GD1b-ganglioside, II3(NeuAc)2GgOse4Cer, Galβ1-3GalNAcβ1-4[NeuAcα2-8NeuAcα2-3]Galβ1-4Glcβ1-1′Cer

GD1b lactone:

GD1b-L, Galβ1-3GalNAcβ1-4[NeuAc(1-9)α2-8NeuAcα2-3]Galβ1-4Glcβ1-1′Cer

Cer:

ceramide

FAB-MS:

fast atom bombardment-mass spectrometry

1H-NMR:

proteon nuclear magnetic resonance

1D-NMR:

one dimensional NMR

2D-COSY:

two dimensional correlated spectroscopy

DMSO-d6 :

deuterated dimethylsulfoxide

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Authors and Affiliations

  1. Study Center for the Functional Biochemistry of Brain Lipids, Department of Biological Chemistry, The Medical School, University of Milan, Via Saldini 50, 20133, Milano, Italy

    Domenico Acquotti, Laura Riboni, Sandro Sonnino & Guido Tettamanti

  2. CNR Study Center for Natural Organic Substances, Department of Chemistry, Polytechnic of Milan, Milano, Italy

    Giovanni Fronza

Authors
  1. Domenico Acquotti
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  2. Giovanni Fronza
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  3. Laura Riboni
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  4. Sandro Sonnino
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  5. Guido Tettamanti
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Acquotti, D., Fronza, G., Riboni, L. et al. Ganglioside lactones:1H-NMR determination of the inner ester position of GD1b-ganglioside lactone naturally occurring in human brain or produced by chemical synthesis. Glycoconjugate J 4, 119–127 (1987). https://doi.org/10.1007/BF01049450

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  • DOI: https://doi.org/10.1007/BF01049450

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