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Perfluoroalkylation of Nitrones for the Synthesis of a Series of Fucosidase Inhibitors

Abstract : Fucosidase inhibitors represent captivating targets for various biological applications. Iminosugars featuring a fluoroalkyl chain in the pseudoanomeric position were synthesized by nucleophilic addition of a perfluoroalkyl Grignard reagent to a nitrone. Reduction of the N–O bond of the hydroxylamine was achieved by treatment with an aqueous solution of sulfur dioxide. The pKa = 4.5 of the target pyrrolidine reflected a strong electronic effect of the fluoroalkyl chain. Inhibitory potencies of the fluorinated iminosugars and their corresponding hydroxylamines were evaluated against α-Lfucosidase at various pH values.
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https://hal.univ-reims.fr/hal-02545754
Contributor : Laurent Dupont <>
Submitted on : Friday, April 17, 2020 - 12:45:53 PM
Last modification on : Wednesday, May 27, 2020 - 7:44:02 AM

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Jadwiga Paszkowska, Olalla Novo Fernandez, Ilona Wandzik, Stéphanie Boudesoque, Laurent Dupont, et al.. Perfluoroalkylation of Nitrones for the Synthesis of a Series of Fucosidase Inhibitors. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (6), pp.1198-1202. ⟨10.1002/ejoc.201403485⟩. ⟨hal-02545754⟩

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