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
The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors / Pearson, Morwenna S. M.; Floquet, Nicolas; Bello, Claudia; Vogel, Pierre; Plantier-Royon, Richard; Szymoniak, Jan; Bertus, Philippe; Behr, Jean-Bernard. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - ELETTRONICO. - 17:(2009), pp. 8020-8026. [10.1016/j.bmc.2009.10.010]
The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors
Bello, Claudia;
2009
Abstract
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
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