Synthesis of C-5a-chain extended derivatives of 4-epi-isofagomine: Powerful β-galactosidase inhibitors and low concentration activators of GM1-gangliosidosis-related human lysosomal β-galactosidase.

Martin Thonhofer, Patrick Weber, Andres Gonzalez Santana, Roland Fischer, Bettina M. Pabst, Eduard Paschke, Michael Schalli, Arnold Stütz, Marion Tschernutter, Werner Windischhofer, Stephen G. Withers

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From an easily available partially protected formal deriv. of 1-deoxymannojirimycin, by hydroxymethyl chain-branching and further elaboration, lipophilic analogs of the powerful β-D-galactosidase inhibitor 4-epi-isofagomine have become available. New compds., e.g. I, exhibit improved inhibitory activities comparable to benchmark compd. NOEV (N-octyl-epi-valienamine) and may serve as leads towards improved and more selective pharmacol. chaperones for GM1-gangliosidosis. [on SciFinder(R)]
Original languageEnglish
Pages (from-to)1438-1442
Number of pages5
JournalBioorganic & Medicinal Chemistry Letters
Issue number5
Publication statusPublished - 2016

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