The University of Southampton
University of Southampton Institutional Repository

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
6408-6411
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
84e4df1a-b6e9-4d7d-98b4-817fb9dc5e49
Galan, M. Carmen
8c06f4d9-ba6d-4c76-8199-736abab1a7e3
Fascione, Martin A.
4262658b-34bc-400a-8ec8-8e2e537b2af5
Flitsch, Sabine L.
74eec2dd-f329-4f0f-999d-73edbcf34e96
Turnbull, W. Bruce
8f23bae9-1cf8-4046-a644-4cb67fc63c99
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
84e4df1a-b6e9-4d7d-98b4-817fb9dc5e49
Galan, M. Carmen
8c06f4d9-ba6d-4c76-8199-736abab1a7e3
Fascione, Martin A.
4262658b-34bc-400a-8ec8-8e2e537b2af5
Flitsch, Sabine L.
74eec2dd-f329-4f0f-999d-73edbcf34e96
Turnbull, W. Bruce
8f23bae9-1cf8-4046-a644-4cb67fc63c99
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, 56 (47), 6408-6411. (doi:10.1039/d0cc02209h).

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.

Text
Chem Comm 3FFuc v3_revised_acc - Accepted Manuscript
Download (461kB)

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
ORCID for Kler Huonnic: ORCID iD orcid.org/0000-0002-8531-2307
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 04 May 2020 16:30
Last modified: 06 Jun 2024 04:21

Export record

Altmetrics

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 ORCID iD
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

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×