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)]
Thonhofer, M., Weber, P.
, Santana, A. G., Fischer, R.
, Pabst, B. M., Paschke, E., ... Withers, S. G. (2016). 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. Bioorganic & Medicinal Chemistry Letters
(5), 1438-1442. https://doi.org/10.1016/j.bmcl.2016.01.059