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

Pablo Valverde; Jean-Baptiste Vendeville; Kristian Hollingsworth; Ashley P Mattey; Tessa Keenan; Harriet Chidwick; Helene Ledru; Kler Huonnic; Kun Huang; Mark E Light; Nicholas Turner; Jesús Jiménez-Barbero; M Carmen Galan; Martin A 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 P Mattey, Tessa Keenan, Harriet Chidwick, Helene Ledru, Kler Huonnic, Kun Huang, Mark E Light, Nicholas Turner, Jesús Jiménez-Barbero, M Carmen Galan, Martin A Fascione, Sabine Flitsch, W Bruce Turnbull, Bruno Linclau

School of Chemistry

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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.

Original language	English
Pages (from-to)	6408-6411
Journal	Chemical communications (Cambridge, England)
Volume	(2020) 56
Early online date	29 Apr 2020
DOIs	https://doi.org/10.1039/d0cc02209h
Publication status	E-pub ahead of print - 29 Apr 2020

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Valverde, P., Vendeville, J.-B., Hollingsworth, K., Mattey, A. P., Keenan, T., Chidwick, H., Ledru, H., Huonnic, K., Huang, K., Light, M. E., Turner, N., Jiménez-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 (Cambridge, England), (2020) 56, 6408-6411. Advance online publication. https://doi.org/10.1039/d0cc02209h

@article{e01511c3eddf4e3cb027d0f8c617a012,

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 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.",

author = "Pablo Valverde and Jean-Baptiste Vendeville and Kristian Hollingsworth and Mattey, {Ashley P} and Tessa Keenan and Harriet Chidwick and Helene Ledru and Kler Huonnic and Kun Huang and Light, {Mark E} and Nicholas Turner and Jes{\'u}s Jim{\'e}nez-Barbero and Galan, {M Carmen} and Fascione, {Martin A} and Sabine Flitsch and Turnbull, {W Bruce} and Bruno Linclau",

year = "2020",

month = apr,

day = "29",

doi = "10.1039/d0cc02209h",

language = "English",

volume = "(2020) 56",

pages = "6408--6411",

journal = "Chemical communications (Cambridge, England)",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

}

Valverde, P, Vendeville, J-B, Hollingsworth, K, Mattey, AP, Keenan, T, Chidwick, H, Ledru, H, Huonnic, K, Huang, K, Light, ME, Turner, N, Jiménez-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 (Cambridge, England), vol. (2020) 56, pp. 6408-6411. 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 P

AU - Keenan, Tessa

AU - Chidwick, Harriet

AU - Ledru, Helene

AU - Huonnic, Kler

AU - Huang, Kun

AU - Light, Mark E

AU - Turner, Nicholas

AU - Jiménez-Barbero, Jesús

AU - Galan, M Carmen

AU - Fascione, Martin A

AU - Flitsch, Sabine

AU - Turnbull, W Bruce

AU - Linclau, Bruno

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 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.

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 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.

U2 - 10.1039/d0cc02209h

DO - 10.1039/d0cc02209h

M3 - Article (Academic Journal)

C2 - 32390019

SN - 1359-7345

VL - (2020) 56

SP - 6408

EP - 6411

JO - Chemical communications (Cambridge, England)

JF - Chemical communications (Cambridge, England)

ER -

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

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