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Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates. 2020
Pablo Valverde, and
Jean-Baptiste Vendeville, and
Kristian Hollingsworth, and
Ashley P Mattey, and
Tessa Keenan, and
Harriet Chidwick, and
Helene Ledru, and
Kler Huonnic, and
Kun Huang, and
Mark E Light, and
Nicholas Turner, and
Jesús Jiménez-Barbero, and
M Carmen Galan, and
Martin A Fascione, and
Sabine Flitsch, and
W Bruce Turnbull, and
Bruno Linclau
School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK. bruno.linclau@soton.ac.uk and CIC bioGUNE, Basque Research and Technology Alliance (BRTA), Bizkaia Technology Park, 48160 Derio, Bizkaia, Spain.
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.
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