Chemoenzymatic synthesis of 3-deoxy-3-fluoro-L-fucose and its enzymatic incorporation into glycoconjugates

Pablo Valverde, Jean-Baptiste Vendeville, Kristian Hollingsworth, Ashley Philip Mattey, Tessa Keenan, Harriet Chidwick, Helene Ledru, Kler Huonnic, Mark E. Light, Nicholas Turner, Jesus Jimenez Barbero, M. Carmen Galan, Martin Anthony Fascione, Sabine Flitsch, W. Bruce Turnbull, Bruno Linclau

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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 -1,2 and an -1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.
Original languageEnglish
JournalChemical Communications
Issue number5
Early online date29 Apr 2020
Publication statusE-pub ahead of print - 29 Apr 2020

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