Issue 47, 2020

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

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

Supplementary files

Article information

Article type
Communication
Submitted
25 Marts 2020
Accepted
28 Apr. 2020
First published
29 Apr. 2020

Chem. Commun., 2020,56, 6408-6411

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, 56, 6408 DOI: 10.1039/D0CC02209H

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