Synthesis and conformational analysis of bicyclic mimics of α- and β-D-glucopyranosides adopting the biologically relevant ²,⁵B conformation.

Luis Amorim, Filipa Marcelo, Jérôme Désiré, Matthieu Sollogoub, Jesús Jiménez-Barbero, Yves Blériot

UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR 7201), FR 2769, C181, 4 place Jussieu, 75005 Paris, France.

Carbohydrate research 2012 Nov 1

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The synthesis of three conformationally locked d-glucopyranoside analogs displaying the hydroxyl pattern of the parent sugar is described. A two carbon bridge connecting the C-2 and C-5 atoms of the pyranose ring allows a torsion of the sugar ring toward a (2,5)B conformation as confirmed by conformational analysis. This conformation is strongly believed to be adopted by the oxacarbenium ion-like transition state of several inverting glucosidases. Copyright © 2012 Elsevier Ltd. All rights reserved.

Citation

Luis Amorim, Filipa Marcelo, Jérôme Désiré, Matthieu Sollogoub, Jesús Jiménez-Barbero, Yves Blériot. Synthesis and conformational analysis of bicyclic mimics of α- and β-D-glucopyranosides adopting the biologically relevant ²,⁵B conformation. Carbohydrate research. 2012 Nov 1;361:219-24