title: Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition.
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.
authors: Department of Chemistry, University of Namur, Rue de Bruxelles 61, 5000 Namur (Belgium).
authors: Inès
authors: I
authors: N'Go
authors: Samuel
authors: S
authors: Golten
authors: Ana
authors: A
authors: Ardá
authors: Javier
authors: J
authors: Cañada
authors: Jesús
authors: J
authors: Jiménez-Barbero
authors: Bruno
authors: B
authors: Linclau
authors: Stéphane P
authors: SP
authors: Vincent
mesh_terms: D001426:Bacterial Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism*; D055162:Biocatalysis; D002241:Carbohydrates / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000378:metabolism; D005461:Fluorine / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D054879:Halogenation; D019751:Intramolecular Transferases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009169:Mycobacterium tuberculosis / Q000201:enzymology; D011485:Protein Binding; D014530:Uridine Diphosphate / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism
chemical_list: D001426:Bacterial Proteins; D002241:Carbohydrates; D004791:Enzyme Inhibitors; C104136:uridine diphosphate galactofuranose; D005461:Fluorine; D014530:Uridine Diphosphate; D019751:Intramolecular Transferases; C098051:UDP-galactopyranose mutase; D005690:Galactose
keywords: NMR spectroscopy; carbohydrates; fluorine; inhibitors; tuberculosis