Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors.
A range of new tetra- and pentahydroxylated seven-membered iminoalditols has been efficiently synthesized from epoxyazepane precursors via nucleophilic opening with hydride or oxygenated species and subsequent hydrogenolysis. One tetrahydroxylated azepane, a ring homologue of deoxymannojirimycin, displays a selective and fairly good inhibition of alpha-L-fucosidase.
Li
Hongqing
H
Ecole Normale Supérieure, Département de Chimie, UMR 8642 associée au CNRS, Paris, France.
Schütz
Catherine
C
Favre
Sylvain
S
Zhang
Yongmin
Y
Vogel
Pierre
P
Sinaÿ
Pierre
P
Blériot
Yves
Y
D017485:1-Deoxynojirimycin; D001381:Azepines / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D013402:Sugar Alcohols / Q000138:chemical synthesis; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
D001381:Azepines; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D013402:Sugar Alcohols; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases; D005644:alpha-L-Fucosidase