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Synthesis of vicinal dideoxy-difluorinated galactoses

Synthesis of vicinal dideoxy-difluorinated galactoses
Synthesis of vicinal dideoxy-difluorinated galactoses
Fluorinated carbohydrates have been employed as probes for fundamental studies of protein–carbohydrate interactions, but also in the development of mechanism-based enzyme inhibitors. There is a continuing demand for novel fluorinated carbohydrate probes. Whereas most examples so far involved monodeoxyfluorinated sugars, multiply deoxyfluorinated sugars have gained much interest. Here we report the synthesis and characterisation of novel vicinal dideoxy-difluorinated D-galactoses with fluorination at the 3,4-positions, and at the 2,3-positions, the latter in both the pyranose and furanose forms. This includes a successful pyranose-into-furanose isomerisation protocol.
1477-0520
Malassis, Julien GJ
5cd4224d-e4db-4835-863c-56b709511ccd
Vendeville, Jean
9f2c6155-cf23-4733-9402-33633fb5bb47
Nguyen, Qui-Hien
11cf45e6-308f-4675-af63-f37eff84f3fe
Boujon, Marie
9b4f5e56-ac0e-457a-989d-3800afbff237
Gaignard-Gaillard, Quentin
71f69c83-ae7a-4ee8-8ded-4f75fa7cf5eb
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Malassis, Julien GJ
5cd4224d-e4db-4835-863c-56b709511ccd
Vendeville, Jean
9f2c6155-cf23-4733-9402-33633fb5bb47
Nguyen, Qui-Hien
11cf45e6-308f-4675-af63-f37eff84f3fe
Boujon, Marie
9b4f5e56-ac0e-457a-989d-3800afbff237
Gaignard-Gaillard, Quentin
71f69c83-ae7a-4ee8-8ded-4f75fa7cf5eb
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba

Malassis, Julien GJ, Vendeville, Jean, Nguyen, Qui-Hien, Boujon, Marie, Gaignard-Gaillard, Quentin, Light, Mark and Linclau, Bruno (2019) Synthesis of vicinal dideoxy-difluorinated galactoses. Organic & Biomolecular Chemistry. (doi:10.1039/C9OB00707E).

Record type: Article

Abstract

Fluorinated carbohydrates have been employed as probes for fundamental studies of protein–carbohydrate interactions, but also in the development of mechanism-based enzyme inhibitors. There is a continuing demand for novel fluorinated carbohydrate probes. Whereas most examples so far involved monodeoxyfluorinated sugars, multiply deoxyfluorinated sugars have gained much interest. Here we report the synthesis and characterisation of novel vicinal dideoxy-difluorinated D-galactoses with fluorination at the 3,4-positions, and at the 2,3-positions, the latter in both the pyranose and furanose forms. This includes a successful pyranose-into-furanose isomerisation protocol.

Text
Linclau difluoroGal revision v2_acc - Accepted Manuscript
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More information

Accepted/In Press date: 8 May 2019
e-pub ahead of print date: 16 May 2019

Identifiers

Local EPrints ID: 431060
URI: http://eprints.soton.ac.uk/id/eprint/431060
ISSN: 1477-0520
PURE UUID: f8121a39-2aa3-4756-9930-f934201e4d27
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: 22 May 2019 16:30
Last modified: 22 Nov 2021 07:23

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Contributors

Author: Julien GJ Malassis
Author: Jean Vendeville
Author: Qui-Hien Nguyen
Author: Marie Boujon
Author: Quentin Gaignard-Gaillard
Author: Mark Light ORCID iD
Author: Bruno Linclau ORCID iD

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