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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
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.
1359-7345
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
19b9cacd-b8e8-4c65-af36-6352cade84ba
Valverde Sanchez, Pablo
22a1719d-0927-409a-a258-9369e07a310e
Vendeville, Jean B
9f2c6155-cf23-4733-9402-33633fb5bb47
Hollingsworth, Kristian
90c656f6-512e-409b-a6ec-22dcdce3193c
Mattey, Ashley
83777a95-e560-440b-b30b-b6b501c178c6
Keenan, Tessa
2480c679-d88c-421b-b697-188a5fa60bcd
Chidwick, Harriet
d2f573d5-98bf-4ffd-bd2b-a11329814258
Ledru, Helene
3f2fb62d-0b88-4b57-a7fc-70749924794e
Huonnic, Kler
095e77fd-6ce1-49df-94c3-584e25a4f2f2
Huang, Kun
75d56bca-ec1e-4aac-bd85-9728abe63722
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Turner, Nicholas
da1a6276-4d43-4767-923b-11889e780231
Jimenez-Barbero, Jesus
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Galan, M. Carmen
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Fascione, Martin A.
4262658b-34bc-400a-8ec8-8e2e537b2af5
Flitsch, Sabine L.
74eec2dd-f329-4f0f-999d-73edbcf34e96
Turnbull, W. Bruce
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Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

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.

Record type: Article

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.

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Chem Comm 3FFuc v3_revised_acc - Accepted Manuscript
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Accepted/In Press date: 28 April 2020
e-pub ahead of print date: 29 April 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
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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Date deposited: 04 May 2020 16:30
Last modified: 28 Apr 2021 04:01

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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: Mark Light ORCID iD
Author: Nicholas Turner
Author: Jesus Jimenez-Barbero
Author: M. Carmen Galan
Author: Martin A. Fascione
Author: Sabine L. Flitsch
Author: W. Bruce Turnbull
Author: Bruno Linclau ORCID iD

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