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Elsevier, Carbohydrate Research, (361), p. 219-224

DOI: 10.1016/j.carres.2012.07.005

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

Journal article published in 2012 by Luis Amorim, Filipa Marcelo ORCID, Jérôme Désiré, Matthieu Sollogoub, Jesús Jiménez-Barbero ORCID, Yves Blériot
This paper is available in a repository.
This paper is available in a repository.

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Abstract

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.