Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 46, Pages 15208-15215Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404180
Keywords
fluorination; glycosyltransferase; NMR spectroscopy; phosphonates; structure elucidation; tuberculosis
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Funding
- ARC grant from the Academie Louvain [A.R.C. 08/13-012]
- FNRS (FRFC grant) [2.4.625.08.F]
- FNRS (F.R.I.A. fellowship)
- MRC [MR/K012118/1] Funding Source: UKRI
- Medical Research Council [MR/K012118/1] Funding Source: researchfish
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Two complementary methods for the synthesis of fluorinated exo-glycals have been developed, for which previously no general reaction had been available. First, a Selectfluor-mediated fluorination was optimized after detailed analysis of all the reaction parameters. A dramatic effect of molecular sieves on the course of the reaction was observed. The reaction was generalized with a set of biologically relevant furanosides and pyranosides. A second direct approach involving carbanionic chemistry and the use of N-fluorobenzenesulfonimide (NFSI) was performed and this method gave better diastereoselectivities. Assignment of the Z/E configuration of all the fluorinated exo-glycals was achieved based on the results of HOESY experiments. Furthermore, fluorinated exo-glycal analogues of UDP-galactofuranose were prepared and assayed against GlfT2, which is a key enzyme involved in the cell-wall biosynthesis of major pathogens. The fluorinated exo-glycals proved to be potent inhibitors as compared with a series of C-glycosidic analogues of UDP-Galf, thus demonstrating the double beneficial effect of the exocyclic enol ether functionality and the fluorine atom.
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