Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates.
Pablo ValverdeJean-Baptiste VendevilleKristian HollingsworthAshley P MatteyTessa KeenanHarriet ChidwickHelene LedruKler HuonnicKun HuangMark E LightNicholas J TurnerJiménez-Barbero JesúsMaria Carmen GalanMartin A FascioneSabine L FlitschW Bruce TurnbullBruno LinclauPublished in: Chemical communications (Cambridge, England) (2021)
The first synthesis of 3-deoxy-3-fluoro-l-fucose is presented, which employs a d- to l-sugar translation strategy, and involves an enzymatic oxidation of 3-deoxy-3-fluoro-l-fucitol. Enzymatic activation (FKP) and glycosylation using an α-1,2 and an α-1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.