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Conformational mobility of oligosaccharides: experimental evidence for the existence of an "anti" conformer of the Galβ1-3Glcβ1-OMe disaccharide

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

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Grosskurth,  Horst
Department of Molecular Neurobiology, Max Planck Institute for Medical Research, Max Planck Society;

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http://pubs.acs.org/doi/pdf/10.1021/ja00125a015
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https://dx.doi.org/10.1021/ja00125a015
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Citation

Dabrowski, J., Kozar, T., Grosskurth, H., & Nifantev, N. E. (1995). Conformational mobility of oligosaccharides: experimental evidence for the existence of an "anti" conformer of the Galβ1-3Glcβ1-OMe disaccharide. Journal of the American Chemical Society, 117(20), 5534-5539. doi:10.1021/ja00125a015.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-41F0-F
Abstract
A hydrogen bond between the Glc OH(4) and Gal OH(2) groups of the title disaccharide, manifested by the doubling of their 1H NMR signals in a partially deuteriated sample in Me2SO solution, proves the existence of an "anti" conformer, i.e., one with the anomeric and transglycosidic aglyconic C-H bonds tumed away from each other by ~180°. This conformer is at equilibrium with the predominating normal "syn" conformation(s), as shown by the analysis of several interresidue NOEs, and confirmed by molecular mechanics and molecular dynamics calculations