title: Synthesis and evaluation of galacto-noeurostegine and its 2-deoxy analogue as glycosidase inhibitors.
abstract: An epimer of the known glycosidase inhibitor noeurostegine, galacto-noeurostegine, was synthesised in 21 steps from levoglucosan and found to be a potent, competitive and highly selective galactosidase inhibitor of Aspergillus oryzae β-galactosidase. Galacto-noeurostegine was not found to be an inhibitor of green coffee bean α-galactosidase, yeast α-glucosidase and E. coli β-galactosidase, whereas potent but non-competitive inhibition against sweet almond β-glucosidase was established. The 2-deoxy-galacto-noeurostegine analogue was also prepared and found to be a less potent inhibitor of the same enzymes.
authors.affiliation: Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000, Aarhus C, Denmark. hhj@chem.au.dk.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Salamone
authors.forename: Lise L
authors.initials: LL
authors.lastname: Clement
authors.forename: Agnete H
authors.initials: AH
authors.lastname: Viuff
authors.forename: Ole Juul
authors.initials: OJ
authors.lastname: Andersen
authors.forename: Frank
authors.initials: F
authors.lastname: Jensen
authors.forename: Henrik H
authors.initials: HH
authors.lastname: Jensen
mesh_terms: D002236:Carbohydrate Conformation; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005643:Fucose / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009662:Nortropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D009662:Nortropanes; C547946:noeurostegine; D005643:Fucose; D006026:Glycoside Hydrolases