title: Synthesis and conformational analysis of bicyclic mimics of α- and β-D-glucopyranosides adopting the biologically relevant ²,⁵B conformation.
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 (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.
authors.affiliation: UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR 7201), FR 2769, C181, 4 place Jussieu, 75005 Paris, France.
authors.forename: Luis
authors.initials: L
authors.lastname: Amorim
authors.forename: Filipa
authors.initials: F
authors.lastname: Marcelo
authors.forename: Jérôme
authors.initials: J
authors.lastname: Désiré
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D005960:Glucosides