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Perfluoroalkylation of Nitrones for the Synthesis of a Series of Fucosidase Inhibitors
Author(s) -
Paszkowska Jadwiga,
Fernandez Olalla Novo,
Wandzik Ilona,
Boudesoque Stéphanie,
Dupont Laurent,
PlantierRoyon Richard,
Behr JeanBernard
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403485
Subject(s) - chemistry , pyrrolidine , hydroxylamine , fucosidase , nucleophile , nitrone , reagent , aqueous solution , combinatorial chemistry , stereochemistry , organic chemistry , cycloaddition , galactose , fucose , catalysis
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.