Synthesis and conformational analysis of bicyclic mimics of alpha- and beta-D-glucopyranosides adopting the biologically relevant 2,5B conformation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Carbohydrate Research Année : 2012

Synthesis and conformational analysis of bicyclic mimics of alpha- and beta-D-glucopyranosides adopting the biologically relevant 2,5B conformation

Résumé

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 B-2,B-5 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.

Dates et versions

hal-00834859 , version 1 (17-06-2013)

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L. Amorim, Farias Marcelo, J. Désiré, M. Sollogoub, J. Jimenez-Barbero, et al.. Synthesis and conformational analysis of bicyclic mimics of alpha- and beta-D-glucopyranosides adopting the biologically relevant 2,5B conformation. Carbohydrate Research, 2012, 361, pp.219-224. ⟨10.1016/j.carres.2012.07.005⟩. ⟨hal-00834859⟩
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