1-Deoxygalactonojirimycin-lysine hybrids as potent D-galactosidase inhibitors.
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.
Steiner
Andreas J
AJ
Glycogroup, Institut für Organische Chemie, Technische Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Schitter
Georg
G
Stütz
Arnold E
AE
Wrodnigg
Tanja M
TM
Tarling
Chris A
CA
Withers
Stephen G
SG
Fantur
Katrin
K
Mahuran
Don
D
Paschke
Eduard
E
Tropak
Michael
M
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*
D004791:Enzyme Inhibitors; D017485:1-Deoxynojirimycin; D005696:Galactosidases; D008239:Lysine