title: 1-Deoxygalactonojirimycin-lysine hybrids as potent D-galactosidase inhibitors.
abstract: Cyclization by double reductive amination of L-arabino-hexos-5-ulose with suitably protected D- as well as L-lysine derivatives provided 1-deoxygalactonojirimycin lysine hybrids without any observable epimer formation at C-5. Modifications on the lysine moiety by acylation gave access to lipophilic derivatives which exhibited excellent D-galactosidase inhibitory activities.
authors.affiliation: Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
authors.forename: Andreas J
authors.initials: AJ
authors.lastname: Steiner
authors.forename: Georg
authors.initials: G
authors.lastname: Schitter
authors.forename: Arnold E
authors.initials: AE
authors.lastname: Stütz
authors.forename: Tanja M
authors.initials: TM
authors.lastname: Wrodnigg
authors.forename: Chris A
authors.initials: CA
authors.lastname: Tarling
authors.forename: Stephen G
authors.initials: SG
authors.lastname: Withers
authors.forename: Katrin
authors.initials: K
authors.lastname: Fantur
authors.forename: Don
authors.initials: D
authors.lastname: Mahuran
authors.forename: Eduard
authors.initials: E
authors.lastname: Paschke
authors.forename: Michael
authors.initials: M
authors.lastname: Tropak
mesh_terms: D017485:1-Deoxynojirimycin / Q000737:chemistry*; D000215:Acylation; D002678:Chimera; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D005696:Galactosidases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D007700:Kinetics; D008239:Lysine / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D017485:1-Deoxynojirimycin; D005696:Galactosidases; D008239:Lysine