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Chemistry. 2014 Jan 3;20(1):106-12. doi: 10.1002/chem.201303693. Epub 2013 Dec 5.

Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition.

Author information

1
Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000 Namur (Belgium).

Abstract

Tetrafluorinated analogues of both UDP-galactopyranose and UDP-galactofuranose have been synthesized and assayed against UDP-galactopyranose mutase, a key enzyme for Mycobacterium tuberculosis cell wall biosynthesis. Competition assays and STD-NMR spectroscopy techniques have evidenced not only the first unambiguous case of affinity enhancement through local sugar polyfluorination, but also showed that tetrafluorination can still have a beneficial effect on binding when monofluorination at the same position does not.

KEYWORDS:

NMR spectroscopy; carbohydrates; fluorine; inhibitors; tuberculosis

PMID:
24311368
DOI:
10.1002/chem.201303693
[Indexed for MEDLINE]

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