Graphical Abstract Biocatalyzed synthesis of difuranosides and their ability to trigger production of TNF-D D Biocatalyzed synthesis of difuranosides and their ability to trigger production of TNF-D D

Ilona Chlubnová (1, 2) , Blanka Králová (1, 2) , Hana Dvořáková (2, 3) , Vojtěch Spiwok (2) , Dominik Filipp (4) , Caroline Nugier-Chauvin (1) , Richard Daniellou (1, 5) , Vincent Ferrières (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Department of Biochemistry and Microbiology
3 Laboratory of NMR spectroscopy
4 Laboratory of Immunobiology
5 ICOA - Institut de Chimie Organique et Analytique

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.

Keywords: Carbohydrates; Furanosides; Immunostimulation

Domains: Life Sciences [q-bio]

Ilona Chlubnová, Blanka Králová, Hana Dvořáková, Vojtěch Spiwok, Dominik Filipp, et al.. Graphical Abstract Biocatalyzed synthesis of difuranosides and their ability to trigger production of TNF-D D Biocatalyzed synthesis of difuranosides and their ability to trigger production of TNF-D D. Bioorganic and Medicinal Chemistry Letters, 2016, 26 (6), pp.1550-1553. ⟨10.1016/j.bmcl.2016.02.018⟩. ⟨hal-01272616⟩