title: Probing the aglycon binding site of a beta-glucosidase: a collection of C-1-modified 2,5-dideoxy-2,5-imino-D-mannitol derivatives and their structure-activity relationships as competitive inhibitors.
abstract: A range of new C-1 modified derivatives of the powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol has been synthesised and their biological activities probed with the beta-glucosidase from Agrobacterium sp. Ki values are compared with those of previously prepared close relatives. Findings suggest dramatic effects exerted by the aglycon binding site on substrate/inhibitor binding.
authors.affiliation: Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
authors.forename: Tanja M
authors.initials: TM
authors.lastname: Wrodnigg
authors.forename: Frederik
authors.initials: F
authors.lastname: Diness
authors.forename: Christoph
authors.initials: C
authors.lastname: Gruber
authors.forename: Herwig
authors.initials: H
authors.lastname: Häusler
authors.forename: Inge
authors.initials: I
authors.lastname: Lundt
authors.forename: Karen
authors.initials: K
authors.lastname: Rupitz
authors.forename: Andreas J
authors.initials: AJ
authors.lastname: Steiner
authors.forename: Arnold E
authors.initials: AE
authors.lastname: Stütz
authors.forename: Chris A
authors.initials: CA
authors.lastname: Tarling
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Withers
authors.forename: Heidrun
authors.initials: H
authors.lastname: Wölfler
mesh_terms: D001667:Binding, Competitive; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D050112:Imino Pyranoses; D008353:Mannitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D012231:Rhizobium / Q000187:drug effects / Q000201:enzymology; D013329:Structure-Activity Relationship; D001617:beta-Glucosidase / Q000737:chemistry* / Q000378:metabolism*
chemical_list: C494911:2,5-dideoxy-2,5-imino-D-mannitol; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D008353:Mannitol; D001617:beta-Glucosidase