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Secondary H/D isotope effect on hydrogen-bonded hydroxyl groups as a tool for recognizing distance constraints in conformational analysis of oligosaccharides

MPG-Autoren
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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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Baust,  Carmen
Max Planck Institute for Medical Research, Max Planck Society;

Externe Ressourcen

http://link.springer.com/content/pdf/10.1023%2FA%3A1008237308320.pdf
(beliebiger Volltext)

https://dx.doi.org/10.1023/A:1008237308320
(beliebiger Volltext)

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Zitation

Dabrowski, J., Grosskurth, H., Baust, C., & Nifantev, N. E. (1998). Secondary H/D isotope effect on hydrogen-bonded hydroxyl groups as a tool for recognizing distance constraints in conformational analysis of oligosaccharides. Journal of Biomolecular NMR, 12(1), 161-172. doi:10.1023/A:1008237308320.


Zitierlink: https://hdl.handle.net/11858/00-001M-0000-002B-9EDF-3
Zusammenfassung
An 'isotopomer-selected NOE' (ISNOE) method for the unequivocal identification of mutually hydrogen-bond-linked hydroxyl groups is described. It relies on the fact that the OH group's signal patterns obtained for a partially deuterated sample originate from both isotopomers of the 'partner' hydroxyl, whereas a NOE for this group can originate from cross-relaxation with the protio isotopomer of this hydroxyl only. Hence, the isotopically shifted component of this group's signal does not appear in a ROE difference spectrum obtained with selective excitation of the 'partner' hydroxyl. This method is also applicable in those cases when only one of two mutually hydrogen-bonded groups exhibits resolvable isotope shifts. Furthermore, it is shown that isotope shifts may occur even for pairs of OH groups that are not mutually hydrogen-bonded, if these participate in hydrogen bonds with other hydroxyls and thereby affect conformational equilibria. The ISNOE experiment enables one to distinguish between these two sources of isotope shifts. Since the O[Symbol: see text][Symbol: see text][Symbol: see text]O distance for hydrogen-bonded hydroxyls in sugars is known to lie between 2.7 and 3.0 A , the hydrogen bonds established by ISNOE can be used in conformational analysis as reliable, motionally non-averaged distance constraints for the conformations containing these bonds.