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

Shuai Wang, Nicolas Galanos, Audric Rousset, Kevin Buffet, Samy Cecioni, Dominique Lafont, Stéphane P. Vincent, Sébastien Vidal

Research output: Contribution to journalArticlepeer-review

Abstract

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/CBr 4-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.

Original languageEnglish
Pages (from-to)15-18
Number of pages4
JournalCarbohydrate Research
Volume395
DOIs
Publication statusPublished - 18 Aug 2014

Keywords

  • Carbohydrate
  • Click chemistry
  • Fucoside
  • Glycosylation
  • Triethyleneglycol

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