Three-dimensional structure of the oligosaccharide chain of GM1 ganglioside 
revealed by a distance-mapping procedure: a rotating and laboratory frame 
nuclear overhauser enhancement investigation of native glycolipid in dimethyl 
sulfoxide and in water-dodecylphosphocholine solutions

Acquotti, Domenico; Poppe, Leszek; Dabrowski, Janusz; von der Lieth, Claus Wilhelm; Sonnino, Sandro; Tettamanti, Guido

doi:10.1021/ja00177a043

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Three-dimensional structure of the oligosaccharide chain of GM1 ganglioside revealed by a distance-mapping procedure: a rotating and laboratory frame nuclear overhauser enhancement investigation of native glycolipid in dimethyl sulfoxide and in water-dodecylphosphocholine solutions

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

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https://pubs.acs.org/doi/pdf/10.1021/ja00177a043
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https://pubs.acs.org/doi/suppl/10.1021/ja00177a043/suppl_file/ja00177a043_si_001.pdf
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https://doi.org/10.1021/ja00177a043
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Supplementary Material (public)

JACS_112_1990_7772_Suppl.pdf
(Supplementary material), 785KB

Citation

Acquotti, D., Poppe, L., Dabrowski, J., von der Lieth, C. W., Sonnino, S., & Tettamanti, G. (1990). Three-dimensional structure of the oligosaccharide chain of GM1 ganglioside revealed by a distance-mapping procedure: a rotating and laboratory frame nuclear overhauser enhancement investigation of native glycolipid in dimethyl sulfoxide and in water-dodecylphosphocholine solutions. Journal of the American Chemical Society, 112(21), 7772-7778. doi:10.1021/ja00177a043.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-ACDB-4

Abstract

Three-dimensional structure of the oligosaccharide part of the GM 1 ganglioside, Galpl-3GalNAcßl -(NeuAca2-3)4Galßl-4GlcßI -1Cer. was modeled with use of a distance-mapping procedure that was based on NOE contacts between amido. hydroxy, and C-linked protons, observed for the intact ganglioside dissolved in Me2SO-d6. The glycosidic linkages of the branched core trisaccharide segment are significantly more rigid than the linkages of the external disaccharide Galßl-3GalNAc and Galßl-4GIc segments, which exist in several conformations. The conformation of the sialic acid side chain seems to be predominantly determined by the hydrogen bond between the C(8)-OH proton and either the carboxylic or ring oxygen. whereas the presence of the acetyl substituent of the C(5)-amino group is irrelevant for this conformation. Similar conformations were found for GM I anchored in mixed D2O/dodecylphosphocholine-d38 micelles