title: Synthesis of substituted exo-glucals via a modified Julia olefination and identification as selective β-glucosidase inhibitors.
abstract: A series of fluorine and non-fluorine-substituted C-glucosylidenes (exo-glucals) has been synthesized via a modified Julia olefination. The deprotected exo-glucals were prepared in five steps from commercially available d-gluconolactone. The evaluation of this original family of compounds against a panel of glycosidases showed a highly specific in vitro activity towards mammalian β-glucosidase depending on the double bond substituents.
authors.affiliation: Laboratoire Chimie Organique 2 Glycochimie, Université de Lyon, ICBMS, UMR 5246 - CNRS, Bat. 308 - Curien (CPE Lyon), Université Claude Bernard Lyon 1, 43 Bd. du 11 Novembre 1918, 69622 Villeurbanne, France. gueyrard@univ-lyon1.fr.
authors.forename: Samuel
authors.initials: S
authors.lastname: Habib
authors.forename: Florent
authors.initials: F
authors.lastname: Larnaud
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Pfund
authors.forename: Teresa
authors.initials: T
authors.lastname: Mena Barragán
authors.forename: Thierry
authors.initials: T
authors.lastname: Lequeux
authors.forename: Carmen
authors.initials: C
authors.lastname: Ortiz Mellet
authors.forename: Peter G
authors.initials: PG
authors.lastname: Goekjian
authors.forename: David
authors.initials: D
authors.lastname: Gueyrard
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000201:enzymology; D013329:Structure-Activity Relationship; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D000475:Alkenes; C438934:C-glycoside; D004791:Enzyme Inhibitors; D006027:Glycosides; D009005:Monosaccharides; D001617:beta-Glucosidase