A short and convenient synthesis of 1-deoxymannojirimycin and N-oxy analogues from D-fructose.
Ketonitrone 8 was prepared from D-fructose as an inexpensive starting material and was used in a stereoselective synthesis of 1-deoxymannojirimycin (DMJ, 4), of its previously unknown N-hydroxy analogue 15, and of the polyhydroxylated ketonitrone 14. The latter were assayed as potential glycosidase inhibitors on a panel of 13 selected purified enzymes. Disappointingly, the polyhydroxylated nitrone 14 inhibited none of these enzymes. However, N-hydroxy-DMJ (15) exhibited a moderate and non-selective activity toward the snail beta-mannosidase EC 3.2.1.25.
Racine
Emilie
E
Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France.
Bello
Claudia
C
Gerber-Lemaire
Sandrine
S
Vogel
Pierre
P
Py
Sandrine
S
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D032449:Canavalia / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005632:Fructose / Q000737:chemistry*; D008361:Mannosidases / Q000037:antagonists & inhibitors; D009589:Nitrogen Oxides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity
D004791:Enzyme Inhibitors; D009589:Nitrogen Oxides; C015388:nitrones; D017485:1-Deoxynojirimycin; D005632:Fructose; D008361:Mannosidases