A Short and Convenient Synthesis of 1-Deoxymannojirimycin (DMJ) and N-oxy-Analogues from D-Fructose
The ketonitrone 8 was prepared from D-fructose as an inexpensive starting material, and was used in a stereoselective synthesis of 1-deoxymannojirimycin (4), its previously unknown N-hydroxy analogue 15, as well as the polyhydroxylated ketonitrone 14. The latter were assayed as potential glycosidase inhibitors on a panel of 13 selected purified enzymes. N-Hydroxy DMJ (15) exhibited a moderate and non selective activity towards the snail - mannosidase EC 18.104.22.168.
Keywords: 1,3-Dipolar Cycloaddition Reactions ; Lysosomal Storage Disorders ; Natural-Product Sb-219383 ; Transfer-Rna Synthetase ; Cyclic Nitrones ; Glycosidase Inhibitors ; Diastereoselective Synthesis ; Absolute-Configuration ; Mannosidase Inhibitor ; Asymmetric-Synthesis
Record created on 2009-01-16, modified on 2016-08-08