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

Pablo Valverde; Jean-Baptiste Vendeville; Kristian Hollingsworth; Ashley Philip Mattey; Tessa Keenan; Harriet Chidwick; Helene Ledru; Kler Huonnic; Mark E. Light; Nicholas Turner; Jesus Jimenez Barbero; M. Carmen Galan; Martin Anthony Fascione; Sabine Flitsch; W. Bruce Turnbull; Bruno Linclau

doi:10.1039/D0CC02209H

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

Pablo Valverde, Jean-Baptiste Vendeville, Kristian Hollingsworth, Ashley Philip Mattey, Tessa Keenan, Harriet Chidwick, Helene Ledru, Kler Huonnic, Mark E. Light, Nicholas Turner, Jesus Jimenez Barbero, M. Carmen Galan, Martin Anthony Fascione, Sabine Flitsch, W. Bruce Turnbull, Bruno Linclau

Chemistry

Research output: Contribution to journal › Article › peer-review

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 -1,2 and an -1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.

Original language	English
Journal	Chemical Communications
Issue number	5
Early online date	29 Apr 2020
DOIs	https://doi.org/10.1039/D0CC02209H
Publication status	E-pub ahead of print - 29 Apr 2020

Bibliographical note

This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

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10.1039/D0CC02209H

d0cc02209h
This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.
Accepted author manuscript, 1.13 MBLicence: Unspecified

https://pubs.rsc.org/en/content/articlelanding/2020/cc/d0cc02209h/unauth#!divAbstractLicence: Unspecified

Modify-Catch-Release-Repeat: Reversible bioconjugations for controlled release of small molecules from antibodies and their fragments
FASCIONE, M. A. (Principal investigator), DAVIES, G. J. (Co-investigator), SOUTHGATE, J. (Co-investigator) & UNGAR, D. (Co-investigator)
EPSRC
1/01/19 → 31/03/23
Project: Research project (funded) › Research

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Valverde, P., Vendeville, J.-B., Hollingsworth, K., Mattey, A. P., Keenan, T., Chidwick, H., Ledru, H., Huonnic, K., Light, M. E., Turner, N., Jimenez Barbero, J., Galan, M. C., Fascione, M. A., Flitsch, S., Turnbull, W. B., & Linclau, B. (2020). Chemoenzymatic synthesis of 3-deoxy-3-fluoro-L-fucose and its enzymatic incorporation into glycoconjugates. Chemical Communications, (5). Advance online publication. https://doi.org/10.1039/D0CC02209H

@article{92192ed4dc674d25a9e3d823ea10a63c,

title = "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 -1,2 and an -1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.",

author = "Pablo Valverde and Jean-Baptiste Vendeville and Kristian Hollingsworth and Mattey, {Ashley Philip} and Tessa Keenan and Harriet Chidwick and Helene Ledru and Kler Huonnic and Light, {Mark E.} and Nicholas Turner and {Jimenez Barbero}, Jesus and Galan, {M. Carmen} and Fascione, {Martin Anthony} and Sabine Flitsch and Turnbull, {W. Bruce} and Bruno Linclau",

note = "This is an author-produced version of the published paper. Uploaded in accordance with the publisher{\textquoteright}s self-archiving policy. Further copying may not be permitted; contact the publisher for details. ",

year = "2020",

month = apr,

day = "29",

doi = "10.1039/D0CC02209H",

language = "English",

journal = "Chemical Communications",

issn = "1364-548X",

publisher = "The Royal Society of Chemistry",

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Valverde, P, Vendeville, J-B, Hollingsworth, K, Mattey, AP, Keenan, T , Chidwick, H, Ledru, H, Huonnic, K, Light, ME, Turner, N, Jimenez Barbero, J, Galan, MC, Fascione, MA, Flitsch, S, Turnbull, WB & Linclau, B 2020, 'Chemoenzymatic synthesis of 3-deoxy-3-fluoro-L-fucose and its enzymatic incorporation into glycoconjugates', Chemical Communications, no. 5. https://doi.org/10.1039/D0CC02209H

TY - JOUR

T1 - Chemoenzymatic synthesis of 3-deoxy-3-fluoro-L-fucose and its enzymatic incorporation into glycoconjugates

AU - Valverde, Pablo

AU - Vendeville, Jean-Baptiste

AU - Hollingsworth, Kristian

AU - Mattey, Ashley Philip

AU - Keenan, Tessa

AU - Chidwick, Harriet

AU - Ledru, Helene

AU - Huonnic, Kler

AU - Light, Mark E.

AU - Turner, Nicholas

AU - Jimenez Barbero, Jesus

AU - Galan, M. Carmen

AU - Fascione, Martin Anthony

AU - Flitsch, Sabine

AU - Turnbull, W. Bruce

AU - Linclau, Bruno

N1 - This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2020/4/29

Y1 - 2020/4/29

N2 - 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 -1,2 and an -1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.

AB - 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 -1,2 and an -1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.

U2 - 10.1039/D0CC02209H

DO - 10.1039/D0CC02209H

M3 - Article

SN - 1364-548X

JO - Chemical Communications

JF - Chemical Communications

IS - 5

ER -

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

Abstract

Bibliographical note

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Modify-Catch-Release-Repeat: Reversible bioconjugations for controlled release of small molecules from antibodies and their fragments

Cite this