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

TitleSynthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors
Publication TypeJournal Article
Year of Publication2010
AuthorsSchitter, G, Scheucher, E, Steiner, AJ, Stuetz, AE, Thonhofer, M, Tarling, CA, Withers, SG, Wicki, J, Fantur, K, Paschke, E, Mahuran, DJ, Rigat, BA, Tropak, M, Wrodnigg, TM
JournalBEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume6
Pagination21
Date PublishedMAR 1
ISSN1860-5397
Abstract

N-Alkylation at the ring nitrogen of the D-galactosidase inhibitor 1-deoxygalactonojirimycin with a functionalised C(6) alkyl chain followed by modification with different aromatic substituents provided lipophilic 1-deoxygalactonojirimycin derivatives which exhibit inhibitory properties against beta-glycosidases from E. coli and Agrobacterium sp. as well as green coffee bean alpha-galactosidase. In preliminary studies, these compounds also showed potential as chemical chaperones for GM1-gangliosidosis related beta-galactosidase mutants.

DOI10.3762/bjoc.6.21