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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| Authors: | Domenico Acquotti Giovanni Fronza Laura Riboni Sandro Sonnino Guido Tettamanti |
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| Affiliation: | (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;(2) CNR Study Center for Natural Organic Substances, Department of Chemistry, Polytechnic of Milan, Milano, Italy |
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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.Abbreviations: Ganglioside nomenclature is according to Svennerholm [16] and the IUPAC-IUB Recommendations [17] GM1 GM1-ganglioside, II3NeuAc-GgOse4Cer, Gal 1-3GalNac1-4[NeuAc 2-3]Gal1-4Glc1-1 Cer - GD1b GD1b-ganglioside, II3(NeuAc)2GgOse4Cer, Gal1-3GalNAc1-4[NeuAc2-8NeuAc2-3]Gal1-4Glc1-1Cer - GD1b lactone GD1b-L, Gal1-3GalNAc1-4[NeuAc(1-9)2-8NeuAc2-3]Gal1-4Glc1-1Cer - 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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| Keywords: | ganglioside lactones NMR |
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