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  High resolution nuclear magnetic resonance spectroscopy of glycosphingolipids. I: 360 MHz 1H and 90.5 MHz 13C NMR analysis of galactosylceramides

Dabrowski, J., Egge, H., & Hanfland, P. (1980). High resolution nuclear magnetic resonance spectroscopy of glycosphingolipids. I: 360 MHz 1H and 90.5 MHz 13C NMR analysis of galactosylceramides. Chemistry and Physics of Lipids, 26(2), 187-196. doi:10.1016/0009-3084(80)90006-7.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0004-9534-9 Version Permalink: https://hdl.handle.net/21.11116/0000-0004-9535-8
Genre: Journal Article

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ChemistPhysLipids_26_1980_187.pdf (Any fulltext), 491KB
 
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Dabrowski, Janusz1, Author           
Egge, Heinz2, Author           
Hanfland , Peter, Author
Affiliations:
1Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society, ou_1497706              
2Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              

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 Abstract: The high resolution 1H and 13C nuclear magnetic resonance (NMR) spectra of galactosylceramides containing n-fatty acids and α-hydroxy fatty acids were recorded in dimethylsulfoxide solution with and without addition of D2O. From the coupling constants of the sugar ring protons, a 4C1 conformation can be deduced. In contrast to the conformation in aqueous solution, the C6 hydroxymethylene group is freely rotating around the C6C5 bond. In the ceramide residue all signals produced by protons linked to carbons bearing electronegative substituents could be attributed. The large difference in coupling constants of the methylene protons of C1′ to the C2′ methine proton of the sphingosine indicates a restricted rotation around the C1′C2′ bond. The assignments of the hydroxy and amino protons follow from the decoupling of the corresponding methine protons.

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Language(s): eng - English
 Dates: 1979-08-171979-11-132003-01-061980-02
 Publication Status: Issued
 Pages: 10
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/0009-3084(80)90006-7
URI: https://www.ncbi.nlm.nih.gov/pubmed/7357686
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Title: Chemistry and Physics of Lipids
  Other : Chem. Phys. Lipids
Source Genre: Journal
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Publ. Info: Amsterdam : Elsevier
Pages: - Volume / Issue: 26 (2) Sequence Number: - Start / End Page: 187 - 196 Identifier: ISSN: 0009-3084
CoNE: https://pure.mpg.de/cone/journals/resource/954925390252