title: Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors.
abstract: 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.
authors.affiliation: Ecole Normale Supérieure, Département de Chimie, UMR 8642 associée au CNRS, Paris, France.
authors.forename: Hongqing
authors.initials: H
authors.lastname: Li
authors.forename: Catherine
authors.initials: C
authors.lastname: Schütz
authors.forename: Sylvain
authors.initials: S
authors.lastname: Favre
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
authors.forename: Pierre
authors.initials: P
authors.lastname: Vogel
authors.forename: Pierre
authors.initials: P
authors.lastname: Sinaÿ
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
mesh_terms: 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*
chemical_list: D001381:Azepines; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D013402:Sugar Alcohols; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases; D005644:alpha-L-Fucosidase