Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 1, Pages 106-112Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303693
Keywords
carbohydrates; fluorine; inhibitors; NMR spectroscopy; tuberculosis
Categories
Funding
- ARC grant from the Academie Louvain [A.R.C. 08/13-012]
- FNRS (FRFC) [2.4.625.08.F, PDR T.0170.13]
- European Community (INTERREG IVa, IS:CE-Chem) [4061]
- EU Dynano ITN [289033]
- COST action [CM1102]
- Ministry of Economy and Competitiveness of Spain [CTQ2012-32025]
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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.
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