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Issue 33, 2013
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Exploration of conformational flexibility and hydrogen bonding of xylosides in different solvents, as a model system for enzyme active site interactions

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Abstract

The predominantly populated conformation of carbohydrates in solution does not necessarily represent the biologically active species; rather, any conformer accessible without too large an energy penalty may be present in a biological pathway. Thus, the conformational preferences of a naphthyl xyloside, which initiates in vivo synthesis of antiproliferative glycosaminoglycans, have been studied by using NMR spectroscopy in a variety of solvents. Equilibria comprising the conformations 4C1, 2SO and 1C4 were found, with a strong dependence on the hydrogen bonding ability of the solvent. Studies of fluorinated analogues revealed a direct hydrogen bond from the hydroxyl group at C2 to the fluorine atom at C4 by a 1hJF4,HO2 coupling. Hydrogen bond directionality was further established via comparisons of fluorinated levoglucosan molecules.

Graphical abstract: Exploration of conformational flexibility and hydrogen bonding of xylosides in different solvents, as a model system for enzyme active site interactions

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Supplementary files

Article information


Submitted
10 May 2013
Accepted
26 Jun 2013
First published
26 Jun 2013

This article is Open Access

Org. Biomol. Chem., 2013,11, 5465-5472
Article type
Paper

Exploration of conformational flexibility and hydrogen bonding of xylosides in different solvents, as a model system for enzyme active site interactions

J. Rönnols, S. Manner, A. Siegbahn, U. Ellervik and G. Widmalm, Org. Biomol. Chem., 2013, 11, 5465
DOI: 10.1039/C3OB40991K

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