NDLI: Selectfluor and NFSI exo-Glycal Fluorination Strategies Applied to the Enhancement of the Binding Affinity of Galactofuranosyltransferase GlfT2 Inhibitors

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Selectfluor and NFSI exo-Glycal Fluorination Strategies Applied to the Enhancement of the Binding Affinity of Galactofuranosyltransferase GlfT2 Inhibitors

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	El Bkassiny, Sandy Ardá, Ana Tikad, Abdellatif Gurcha, Sudagar S. Besra, Gurdyal S. Eppe, Guillaume Jiménez-barbero, Jesús Vincent, Stéphane P. Dumitrescu, Lidia Pan, Weidong
Description	Author Affiliation: Dumitrescu L ( University of Namur (UNamur), Département de Chimie, Laboratoire de Chimie Bio-Organique rue de Bruxelles 61, B-5000 Namur (Belgium), Fax: (+32) 81-72-45-17.)
Abstract	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.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	46
Volume Number	20
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2014-11-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Diazonium Compounds Chemistry Enzyme Inhibitors Galactose Analogs & Derivatives Galactosyltransferases Antagonists & Inhibitors Sulfonamides Uridine Diphosphate Antitubercular Agents Chemical Synthesis Pharmacology Metabolism Halogenation Models, Molecular Mycobacterium Tuberculosis Enzymology Tuberculosis Drug Therapy Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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