title: Biocatalyzed synthesis of difuranosides and their ability to trigger production of TNF-α.
abstract: Transglycosylation reactions biocatalyzed by the native arabinofuranosidase Araf51 and using d-galactosyl, d-fucosyl and 6-deoxy-6-fluoro-D-galactosyl derivatives as donors and acceptors provided di-to pentahexofuranosides. The immunostimulatory potency of these compounds, and more especially their ability to induce production of TNF-α, was evaluated on the murine macrophage cell line, Raw 264.7. The results obtained showed concentration-dependent and most importantly, structure-dependent responses. Interestingly, oligoarabinofuranosides belonging to the oligopentafuranoside family displayed concentration-, chain length and aglycon-dependent bioactivities irrespective of their fine chemical variations. Thus, neo-oligofuranosides in D-Galf series, as well as their D-Fucf and 6-fluorinated counterparts are indeed potential sources of immunostimulating agents.
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France; Université européenne de Bretagne, France; Department of Biochemistry and Microbiology, Institute of Chemical Technology of Prague, Techniká 3, 166 28 Prague 6, Czech Republic; Laboratory of Immunobiology, Institute of Molecular Genetics AS CR, Videnska 1083, 142 20 Prague 4, Czech Republic.
authors.forename: Ilona
authors.initials: I
authors.lastname: Chlubnová
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France; Department of Biochemistry and Microbiology, Institute of Chemical Technology of Prague, Techniká 3, 166 28 Prague 6, Czech Republic.
authors.forename: Blanka
authors.initials: B
authors.lastname: Králová
authors.affiliation: Department of Biochemistry and Microbiology, Institute of Chemical Technology of Prague, Techniká 3, 166 28 Prague 6, Czech Republic; Laboratory of NMR Spectroscopy, Institute of Chemical Technology of Prague, Techniká 5, 166 28 Prague 6, Czech Republic.
authors.forename: Hana
authors.initials: H
authors.lastname: Dvořáková
authors.affiliation: Department of Biochemistry and Microbiology, Institute of Chemical Technology of Prague, Techniká 3, 166 28 Prague 6, Czech Republic.
authors.forename: Vojtěch
authors.initials: V
authors.lastname: Spiwok
authors.affiliation: Laboratory of Immunobiology, Institute of Molecular Genetics AS CR, Videnska 1083, 142 20 Prague 4, Czech Republic.
authors.forename: Dominik
authors.initials: D
authors.lastname: Filipp
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France; Université européenne de Bretagne, France.
authors.forename: Caroline
authors.initials: C
authors.lastname: Nugier-Chauvin
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France; Université européenne de Bretagne, France.
authors.forename: Richard
authors.initials: R
authors.lastname: Daniellou
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France; Université européenne de Bretagne, France. Electronic address: vincent.ferrieres@ensc-rennes.fr.
authors.forename: Vincent
authors.initials: V
authors.lastname: Ferrières
mesh_terms: D000818:Animals; D055162:Biocatalysis; D002236:Carbohydrate Conformation; D002460:Cell Line; D004187:Disaccharides / Q000096:biosynthesis* / Q000737:chemistry / Q000276:immunology / Q000494:pharmacology*; D051379:Mice; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis*
chemical_list: D004187:Disaccharides; D014409:Tumor Necrosis Factor-alpha
keywords: Carbohydrates; Furanosides; Immunostimulation