title: C-5a-substituted validamine type glycosidase inhibitors.
abstract: A series of N-alkyl derivatives of the D-galactosidase inhibitor 1,4-di-epi-validamine featuring lipophilic substituents at position C-5a was prepared and screened for their glycosidase inhibitory properties. Products turned out selective for β-galactosidases as well as β-glucosidases.
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
authors.forename: Michael
authors.initials: M
authors.lastname: Schalli
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
authors.forename: Andreas
authors.initials: A
authors.lastname: Wolfsgruber
authors.affiliation: Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
authors.forename: Andres
authors.initials: A
authors.lastname: Gonzalez Santana
authors.affiliation: Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
authors.forename: Christina
authors.initials: C
authors.lastname: Tysoe
authors.affiliation: Institute of Inorganic Chemistry Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
authors.forename: Roland
authors.initials: R
authors.lastname: Fischer
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria. Electronic address: stuetz@tugraz.at.
authors.forename: Arnold E
authors.initials: AE
authors.lastname: Stütz
authors.affiliation: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.
authors.forename: Martin
authors.initials: M
authors.lastname: Thonhofer
authors.affiliation: Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Withers
mesh_terms: D060054:Agrobacterium / Q000737:chemistry / Q000201:enzymology; D000818:Animals; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D004926:Escherichia coli / Q000737:chemistry / Q000201:enzymology; D005656:Fungal Proteins / Q000037:antagonists & inhibitors* / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007700:Kinetics; D012441:Saccharomyces cerevisiae / Q000737:chemistry / Q000201:enzymology; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors* / Q000737:chemistry
chemical_list: D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D005656:Fungal Proteins; C042908:validamine; D007294:Inositol; D001617:beta-Glucosidase; D001616:beta-Galactosidase
keywords: Aminocyclitol; Carbasugar; Glycosidase inhibitor