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High resolution proton NMR spectra of blood-group active glycosphingolipids in DMSO-d6

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Dabrowski,  Janusz
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Dabrowski, J., EGGE, H., HANFLAND, P., & KUHN, S. (1980). High resolution proton NMR spectra of blood-group active glycosphingolipids in DMSO-d6. In Cell Surface Glycolipids (Chapter 4, pp. 55-64). Washington, DC: American Chemical Society.


Cite as: https://hdl.handle.net/21.11116/0000-0004-9796-8
Abstract
It has been shown recently that the application of high resolution proton magnetic resonance spectroscopy is a useful technique for the structural elucidation of glycosphingolipids. Martin-Lomas and Chapman (1) and the group of Karlsson (2) investigated acetylated and methylated and reduced derivatives of glycosphingolipids. This group succeeded in analyzing non- derivatized cerebrosides (3) and higher glycosphingolipids by high resolution NMR spectroscopy. In order to avoid solubility problems, like formation of micelles and aggregates in aqueous solution, these products have been successfully measured in DMSO-d6. In simpler glycosphingolipids such as glucosylceramide, galactosylceramide and lactosylceramide the signals of all protons that are linked to carbons bearing negatively charged substituents could be assigned. In this paper the results obtained with some of the more complex glycosphingolipids are presented.

In the oligosaccharide moiety of these glycosphingolipids, well analyzed by conventional methods, the linkages of the sugar components glucose, galactose, N-acetyl-glucosamine and N-acetylgalactosamine exhibit a