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

Pablo Valverde, Jean-Baptiste Vendeville, Kristian Hollingsworth, Ashley P Mattey, Tessa Keenan, Harriet Chidwick, Helene Ledru, Kler Huonnic, Kun Huang, Mark E Light, Nicholas Turner, Jesús Jiménez-Barbero, M Carmen Galan, Martin A Fascione, Sabine Flitsch, W Bruce Turnbull, Bruno Linclau

Research output: Contribution to journalArticle (Academic Journal)

Abstract

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.

Original languageEnglish
Pages (from-to)6408-6411
JournalChemical communications (Cambridge, England)
Volume(2020) 56
Early online date29 Apr 2020
DOIs
Publication statusE-pub ahead of print - 29 Apr 2020

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