A Short and Convenient Synthesis of 1-Deoxymannojirimycin and N-Oxy Analogues from D-Fructose.
Ketonitrone I was prepd. from D-fructose as an inexpensive starting material and was used in a stereoselective synthesis of 1-deoxymannojirimycin (DMJ), of its previously unknown N-hydroxy analog II, and of the polyhydroxylated ketonitrone III. The latter were assayed as potential glycosidase inhibitors on a panel of 13 selected purified enzymes. Disappointingly, the polyhydroxylated nitrone III inhibited none of these enzymes. However, II exhibited a moderate and non-selective activity toward the snail $\beta$-mannosidase EC 3.2.1.25. [on SciFinder(R)]
Références
- Titre
- A Short and Convenient Synthesis of 1-Deoxymannojirimycin and N-Oxy Analogues from D-Fructose.
- Type de publication
- Article de revue
- Année de publication
- 2009
- Auteurs
- Racine, Emilie, Bello Claudia, Gerber-Lemaire Sandrine, Vogel Pierre, and Py Sandrine
- Revue
- J. Org. Chem.
- Volume
- 74
- Pagination
- 1766–1769
- ISSN
- 0022-3263
Soumis le 12 avril 2018