Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors.
N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C ₆alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-glycosidases from E. coli and Agrobacterium sp. as well as green coffee bean α-galactosidase. In preliminary studies, these compounds also showed potential as chemical chaperones for GM1-gangliosidosis related β-galactosidase mutants.
Schitter
Georg
G
Glycogroup, Institute for Organic Chemistry, University of Technology Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Scheucher
Elisabeth
E
Steiner
Andreas J
AJ
Stütz
Arnold E
AE
Thonhofer
Martin
M
Tarling
Chris A
CA
Withers
Stephen G
SG
Wicki
Jacqueline
J
Fantur
Katrin
K
Paschke
Eduard
E
Mahuran
Don J
DJ
Rigat
Brigitte A
BA
Tropak
Michael
M
Wrodnigg
Tanja M
TM