title: Synthesis of polyhydroxylated piperidines and evaluation as glycosidase inhibitors.
abstract: A series of 16 new chiral nonracemic polyhydroxylated piperidines was synthesized utilizing several chiral beta-amino-alcohols. They act as a nitrogen source, chirality inducer and iminium stabilizer, in the desymmetrization of meso-trihydroxylated glutaraldehyde. The biological activity of these compounds towards several glycosidases (alpha-D-glucosidase, alpha-D-mannosidase, alpha-L-fucosidase) has been evaluated.
authors.affiliation: Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, UMR 8638 associée au CNRS et à l'Université René Descartes, 4, Avenue de l'Observatoire, 75270 Paris Cedex 06, France.
authors.forename: Tony
authors.initials: T
authors.lastname: Tite
authors.forename: Marie-Christine
authors.initials: MC
authors.lastname: Lallemand
authors.forename: Erwan
authors.initials: E
authors.lastname: Poupon
authors.forename: Nicole
authors.initials: N
authors.lastname: Kunesch
authors.forename: François
authors.initials: F
authors.lastname: Tillequin
authors.forename: Christine
authors.initials: C
authors.lastname: Gravier-Pelletier
authors.forename: Yves
authors.initials: Y
authors.lastname: Le Merrer
authors.forename: Henri-Philippe
authors.initials: HP
authors.lastname: Husson
mesh_terms: D001426:Bacterial Proteins / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D001411:Geobacillus stearothermophilus / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors
chemical_list: D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D010880:Piperidines; D006026:Glycoside Hydrolases; D043323:alpha-Mannosidase; D005644:alpha-L-Fucosidase