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5-Fluoro derivatives of 4-epi-isofagomine as D-galactosidase inhibitors and potential pharmacological chaperones for G(M1)-gangliosidosis as well as Fabry's disease

Title5-Fluoro derivatives of 4-epi-isofagomine as D-galactosidase inhibitors and potential pharmacological chaperones for G(M1)-gangliosidosis as well as Fabry's disease
Publication TypeJournal Article
Year of Publication2016
AuthorsThonhofer, M, Santana, AGonzalez, Fischer, R, Gomez, ATorvisco, Saf, R, Schalli, M, Stuetz, AE, Withers, SG
JournalCARBOHYDRATE RESEARCH
Volume420
Pagination6-12
Date PublishedFEB
ISSN0008-6215
Abstract

Electrophilic fluorination of an exocyclic methoxymethylene enol ether derived from N-tertbutyloxycarbonyl- 1,5-dideoxy-1,5-imino-3,4-O-isopropylidene-D-erythro-pent-2-ulose (11) provided the 5-fluoro derivative of the powerful beta-galactosidase inhibitor 4-epi-isofagomine (8). This structural alteration, in combination with N-alkylation, led to considerably improved alpha-galactosidase selectivity. New compounds may serve as leads en route to new pharmacological chaperones for Fabry's disease. (C) 2015 Elsevier Ltd. All rights reserved.

DOI10.1016/j.carres.2015.10.009