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The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors |
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| Authors: | Morwenna S.M. Pearson Nicolas Floquet Claudia Bello Pierre Vogel Richard Plantier-Royon Jan Szymoniak Philippe Bertus Jean-Bernard Behr |
| Affiliation: | 1. Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 6229, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims Cedex 2, France;2. Institut des Biomolécules Max Mousseron (I.B.M.M.), CNRS UMR 5247, Université Montpellier 1, Université Montpellier 2, Faculté de Pharmacie, 15 rue Charles Flahault, BP 14491, 34093 Montpellier Cedex 5, France;3. Laboratoire de Glycochimie et Synthèse Asymétrique, Ecole Polytechnique Fédérale de Lausanne (EPFL), BCH CH-1015 Lausanne, Switzerland;4. Unité de Chimie Organique Moléculaire et Macromoléculaire, CNRS and Université du Maine, UMR 6011—UCO2M, 72085 Le Mans Cedex 9, France |
| 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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