Synthesis of Novel DC-SIGN Ligands with an α-Fucosylamide Anchor (pages 1921–1930)
Gabriele Timpano, Georges Tabarani, Marko Anderluh, Donatella Invernizzi, Francesca Vasile, Donatella Potenza, Pedro M. Nieto, Javier Rojo, Franck Fieschi and Anna Bernardi
Article first published online: 24 JUL 2008 | DOI: 10.1002/cbic.200800139
Stop DC-SIGN: Based on the known 3D structure of the Lewis-x trisaccharide, monovalent α-fucosylamides that bind to the dendritic cell receptor DC-SIGN were synthesized. Their inhibitory constants were assessed by using SPR and their interactions with DC-SIGN were characterized by STD NMR spectroscopy. For the first time, α-fucosylamides were shown to perform as functional mimics of unstable α-fucosides and to block DC-SIGN with good affinity.