|Title||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|
|Publication Type||Journal Article|
|Year of Publication||2016|
|Authors||Thonhofer, M, Santana, AGonzalez, Fischer, R, Gomez, ATorvisco, Saf, R, Schalli, M, Stuetz, AE, Withers, SG|
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.