title: Fucosylation of triethyleneglycol-based acceptors into 'clickable' α-fucosides.
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/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.
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Shuai
authors.initials: S
authors.lastname: Wang
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Galanos
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Audric
authors.initials: A
authors.lastname: Rousset
authors.affiliation: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000 Namur, Belgium.
authors.forename: Kevin
authors.initials: K
authors.lastname: Buffet
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Samy
authors.initials: S
authors.lastname: Cecioni
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France.
authors.forename: Dominique
authors.initials: D
authors.lastname: Lafont
authors.affiliation: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000 Namur, Belgium.
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
authors.affiliation: Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CO2-Glyco, UMR 5246, CNRS, Université Claude Bernard Lyon 1, Université de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France. Electronic address: sebastien.vidal@univ-lyon1.fr.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Vidal
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D005026:Ethylene Glycols / Q000737:chemistry*; D005643:Fucose / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation
chemical_list: D000480:Alkynes; D001386:Azides; D005026:Ethylene Glycols; D006001:Glycoconjugates; D005643:Fucose
keywords: Carbohydrate; Click chemistry; Fucoside; Glycosylation; Triethyleneglycol