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

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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.

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

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Article information


Submitted
25 Mar 2020
Accepted
28 Apr 2020
First published
29 Apr 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

P. Valverde, J. Vendeville, K. Hollingsworth, A. P. Mattey, T. Keenan, H. Chidwick, H. Ledru, K. Huonnic, K. Huang, M. E. Light, N. Turner, J. Jiménez-Barbero, M. C. Galan, M. A. Fascione, S. Flitsch, W. B. Turnbull and B. Linclau, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02209H

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