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 a-1,2 and an a-1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.
6408-6411
Valverde Sanchez, Pablo
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Vendeville, Jean B
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Hollingsworth, Kristian
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Mattey, Ashley
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Keenan, Tessa
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Chidwick, Harriet
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Ledru, Helene
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Huonnic, Kler
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Huang, Kun
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Light, Mark
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Turner, Nicholas
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Jimenez-Barbero, Jesus
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Galan, M. Carmen
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Fascione, Martin A.
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Flitsch, Sabine L.
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Turnbull, W. Bruce
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Linclau, Bruno
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14 June 2020
Valverde Sanchez, Pablo
22a1719d-0927-409a-a258-9369e07a310e
Vendeville, Jean B
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Hollingsworth, Kristian
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Mattey, Ashley
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Keenan, Tessa
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Chidwick, Harriet
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Ledru, Helene
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Huonnic, Kler
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Huang, Kun
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Light, Mark
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Turner, Nicholas
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Jimenez-Barbero, Jesus
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Galan, M. Carmen
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Fascione, Martin A.
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Flitsch, Sabine L.
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Turnbull, W. Bruce
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Linclau, Bruno
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Valverde Sanchez, Pablo, Vendeville, Jean B, Hollingsworth, Kristian, Mattey, Ashley, Keenan, Tessa, Chidwick, Harriet, Ledru, Helene, Huonnic, Kler, Huang, Kun, Light, Mark, Turner, Nicholas, Jimenez-Barbero, Jesus, Galan, M. Carmen, Fascione, Martin A., Flitsch, Sabine L., Turnbull, W. Bruce and Linclau, Bruno
(2020)
Chemoenzymatic synthesis of 3-deoxy-3-fluoro-L-fucose and its enzymatic incorporation into glycoconjugates.
Chemical Communications, 56 (47), .
(doi:10.1039/d0cc02209h).
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 a-1,2 and an a-1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.
Text
Chem Comm 3FFuc v3_revised_acc
- Accepted Manuscript
More information
Accepted/In Press date: 28 April 2020
e-pub ahead of print date: 29 April 2020
Published date: 14 June 2020
Additional Information:
Funding Information:
We are grateful to T. Kaminski and M. E. Webb for their contribution in expressing galactosyltransferase enzymes. This project has been funded by the Industrial Biotechnology Catalyst (Innovate UK, BBSRC, EPSRC, BB/M028941/1, BB/M028747/1, BB/ M028976, BB/M02487X/1) to support the translation, development and commercialization of innovative Industrial Biotechnology processes. BL also thanks the EPSRC (EP/K039466/1), and SF thanks IBioIC, Prozomix Ltd and Bio-shape Ltd, RCUK (BB/L013762/1; BB/M027791/1; BB/M028836/1) and ERC (788231-ProgrES-ERC-2017-ADG) for funding. MCG thanks European Research Council (ERC-COG: 648239). JJB thanks the Agencia Estatal de Investigación (Spain) (RTI2018-094751-B-C21 and SEV-2016-0644), and ERC (788143-RECGLYCANMR-ERC-2017-ADG) for funding, and the Ministerio de Educación, Cultura y Deporte | FPU fellowship (FPU-2014-06147) to PV.
Publisher Copyright:
© The Royal Society of Chemistry 2020.
Identifiers
Local EPrints ID: 439782
URI: http://eprints.soton.ac.uk/id/eprint/439782
ISSN: 1359-7345
PURE UUID: e5a0b13a-692e-403c-afea-14abcb476c09
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Date deposited: 04 May 2020 16:30
Last modified: 17 Mar 2024 05:31
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Contributors
Author:
Pablo Valverde Sanchez
Author:
Jean B Vendeville
Author:
Kristian Hollingsworth
Author:
Ashley Mattey
Author:
Tessa Keenan
Author:
Harriet Chidwick
Author:
Helene Ledru
Author:
Kler Huonnic
Author:
Kun Huang
Author:
Nicholas Turner
Author:
Jesus Jimenez-Barbero
Author:
M. Carmen Galan
Author:
Martin A. Fascione
Author:
Sabine L. Flitsch
Author:
W. Bruce Turnbull
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