Fucosylation of triethyleneglycol-based acceptors into 'clickable' α-fucosides - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Carbohydrate Research Année : 2014

Fucosylation of triethyleneglycol-based acceptors into 'clickable' α-fucosides

K. Buffet
  • Fonction : Auteur
Sp Vincent
  • Fonction : Auteur
S. Vidal

Résumé

Design of multivalent glycoconjugates can find applications such as in anti-adhesive therapy against bacterial infections. Nevertheless, the access to such macromolecules requires functionalized building blocks prepared in a minimum number of steps and on a multi-gram scale at least for the laboratory. Fucose is a representative epitope used by several bacteria for adhesion to their host cells. The stereoselective, rapid, and efficient access to two 'clickable' α-fucosides was re-investigated using PPh3/CBr4-promoted glycosylation of chloro- (as precursors of azido-) and alkyne-functionalized triethyleneglycols with fully unprotected l-fucose. The convenient access to such building blocks paves the way to the design of new multivalent glycoconjugates functionalized with fucose epitopes and their applications

Domaines

Chimie organique
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Dates et versions

hal-01147398 , version 1 (30-04-2015)

Identifiants

Citer

S. Wang, N. Galanos, A. Rousset, K. Buffet, S. Cecioni, et al.. Fucosylation of triethyleneglycol-based acceptors into 'clickable' α-fucosides. Carbohydrate Research, 2014, 395, pp.15-18. ⟨10.1016/j.carres⟩. ⟨hal-01147398⟩
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