Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition
Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition
Tetrafluorinated analogues of both UDP-galactosylpyranose and UDP-galactosylfuranose have been synthesized and assayed against UDP-galactopyranose mutase, a key enzyme of M. tuberculosis cell wall biosynthesis. Competition assays and STD-NMR techniques have evidenced not only the first unambiguous case of affinity enhancement through local sugar perfluorination, but also showed that tetrafluorination can still have a beneficial effect on binding when monofluorination at the same position does not.
carbohydrates, fluorine, inhibitors, nmr, spectroscopy, tuberculosis
106-112
N'Go, Inès
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Golten, Samuel
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Ardá, Ana
381d3f7d-6c5a-427a-8433-bdfc02da3a6d
Cañada, Javier
a8e2f7d7-3542-4ba7-9031-3ee48a30876a
Jiménez-Barbero, Jesús
8d249106-a8a2-40ff-bcf0-e16ee3b75d32
Linclau, Bruno
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Vincent, Stéphane P.
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3 January 2014
N'Go, Inès
3bb94c75-9b3c-42c0-8615-85ba636bf40d
Golten, Samuel
214a0aed-950c-41b0-8b3f-b71614ce9d5e
Ardá, Ana
381d3f7d-6c5a-427a-8433-bdfc02da3a6d
Cañada, Javier
a8e2f7d7-3542-4ba7-9031-3ee48a30876a
Jiménez-Barbero, Jesús
8d249106-a8a2-40ff-bcf0-e16ee3b75d32
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Vincent, Stéphane P.
c1d1d147-b144-4e4c-9bf7-c1bc644587df
N'Go, Inès, Golten, Samuel, Ardá, Ana, Cañada, Javier, Jiménez-Barbero, Jesús, Linclau, Bruno and Vincent, Stéphane P.
(2014)
Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition.
Chemistry - A European Journal, 20 (1), .
(doi:10.1002/chem.201303693).
Abstract
Tetrafluorinated analogues of both UDP-galactosylpyranose and UDP-galactosylfuranose have been synthesized and assayed against UDP-galactopyranose mutase, a key enzyme of M. tuberculosis cell wall biosynthesis. Competition assays and STD-NMR techniques have evidenced not only the first unambiguous case of affinity enhancement through local sugar perfluorination, but also showed that tetrafluorination can still have a beneficial effect on binding when monofluorination at the same position does not.
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e-pub ahead of print date: 5 December 2013
Published date: 3 January 2014
Keywords:
carbohydrates, fluorine, inhibitors, nmr, spectroscopy, tuberculosis
Organisations:
Molecular Diagnostics & Thereputics
Identifiers
Local EPrints ID: 359585
URI: http://eprints.soton.ac.uk/id/eprint/359585
ISSN: 0947-6539
PURE UUID: 1140317f-f754-47c7-8863-2423f2dd69b8
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Date deposited: 05 Nov 2013 11:15
Last modified: 15 Mar 2024 03:05
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Contributors
Author:
Inès N'Go
Author:
Samuel Golten
Author:
Ana Ardá
Author:
Javier Cañada
Author:
Jesús Jiménez-Barbero
Author:
Stéphane P. Vincent
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