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

doi:10.1039/D0CC02209H

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

Pablo Valverde,

‡^ab Jean-Baptiste Vendeville,‡^a Kristian Hollingsworth,

‡^c Ashley P. Mattey,

^d Tessa Keenan,

^e Harriet Chidwick,^e Helene Ledru,^f Kler Huonnic,^a Kun Huang,

^d Mark E. Light,

^a Nicholas Turner,

^d Jesús Jiménez-Barbero,

^cgh M. Carmen Galan,

^f Martin A. Fascione,

^e Sabine Flitsch,

*^d W. Bruce Turnbull

*^c and Bruno Linclau

*^a

Author affiliations

* Corresponding authors

^a School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK
E-mail: bruno.linclau@soton.ac.uk

^b CIC bioGUNE, Basque Research and Technology Alliance (BRTA), Bizkaia Technology Park, 48160 Derio, Bizkaia, Spain

^c School of Chemistry and Astbury Centre for Structural Molecular Biology, University of Leeds, Leeds, UK
E-mail: W.B.Turnbull@leeds.ac.uk

^d Manchester Institute of Biotechnology (MIB), School of Chemistry, University of Manchester, 131 Princess Street, Manchester, UK
E-mail: Sabine.Flitsch@manchester.ac.uk

^e Department of Chemistry, University of York, Heslington, York, UK

^f School of Chemistry, Cantock's Close, University of Bristol, Bristol, UK

^g Ikerbasque, Basque Foundation for Science, Maria Diaz de Haro 3, 48013 Bilbao, Spain

^h Department Organic Chemistry II, Faculty Science & Technology, EHU-UPV, Leioa, Spain

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.

This article is part of the themed collection: Celebrating our 2024 Prizewinners

Chemical Communications

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

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

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