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Article Dans Une Revue Bioorganic and Medicinal Chemistry Année : 2009

The spirocyclopropyl moiety as a methyl surrogate in the structure of L-fucosidase and L-rhamnosidase inhibitors

Résumé

Nitrogen-in-the-ring analogues of l-fucose and l-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile as the key step. Four new spirocyclopropyl iminosugar analogues were generated, which displayed some activity towards l-fucosidase and l-rhamnosidase.

Domaines

Chimie organique

Dates et versions

hal-00439568 , version 1 (07-12-2009)

Identifiants

Citer

Morwenna Pearson, Nicolas Floquet, Claudia Bello, Pierre Vogel, Richard Plantier-Royon, et al.. The spirocyclopropyl moiety as a methyl surrogate in the structure of L-fucosidase and L-rhamnosidase inhibitors. Bioorganic and Medicinal Chemistry, 2009, 17 (23), pp.8020-8026. ⟨10.1016/j.bmc.2009.10.010⟩. ⟨hal-00439568⟩
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