Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

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 C6 alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against β-glyc...

Full description

Bibliographic Details
Main Authors: Georg Schitter, Elisabeth Scheucher, Andreas J. Steiner, Arnold E. Stütz, Martin Thonhofer, Chris A. Tarling, Stephen G. Withers, Jacqueline Wicki, Katrin Fantur, Eduard Paschke, Don J. Mahuran, Brigitte A. Rigat, Michael Tropak, Tanja M. Wrodnigg
Format: Article
Language:English
Published: Beilstein-Institut 2010-03-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
chemical chaperones
1-deoxy-D-galactonojirimycin
iminosugars
lipophilic galactosidase inhibitor
N-modified iminosugars
Online Access:https://doi.org/10.3762/bjoc.6.21
Description
Summary:N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C6 alkyl 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.
ISSN:1860-5397

Similar Items