1. Perfluoroalkylation of Nitrones for the Synthesis of a Series of Fucosidase Inhibitors.
- Author
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Paszkowska, Jadwiga, Fernandez, Olalla Novo, Wandzik, Ilona, Boudesoque, Stéphanie, Dupont, Laurent, Plantier‐Royon, Richard, and Behr, Jean‐Bernard
- Subjects
FUCOSIDASES ,NITRONES ,IMINOSUGARS ,FLUOROALKYL group ,AQUEOUS solutions ,NUCLEOPHILIC addition (Chemistry) - 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 p K
a = 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- L-fucosidase at various pH values. [ABSTRACT FROM AUTHOR]- Published
- 2015
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