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

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

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...

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Hauptverfasser: Valverde, Pablo, Vendeville, Jean-Baptiste, Hollingsworth, Kristian, Mattey, Ashley Philip, Keenan, Tessa, Chidwick, Harriet, Ledru, Helene, Huonnic, Kler, Light, Mark E, Turner, Nicholas, Jimenez Barbero, Jesus, Galan, M. Carmen, Fascione, Martin Anthony, Flitsch, Sabine, Turnbull, W. Bruce, Linclau, Bruno
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Sprache:eng
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Zusammenfassung: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.
DOI:10.1039/D0CC02209H