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SHR Neuro Krebs Kardio Lipid

Lebl, R; Thonhofer, M; Tysoe, C; Pabst, BM; Schalli, M; Weber, P; Paschke, E; Stütz, AE; Tschernutter, M; Windischhofer, W; Withers, SG.
A Morita-Baylis-Hillman based route to C-5a-chain-extended 4-epi-isofagomine type glycosidase inhibitors.
Carbohydr Res. 2017; 442(6):31-40
Web of Science PubMed FullText FullText_MUG

 

Autor/innen der Med Uni Graz:
Pabst Bettina
Paschke Eduard
Tschernutter Marion
Windischhofer Werner
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Abstract:
By Morita-Baylis-Hillman reaction of 2,3-O-isopropylidene-D-glyceraldehyde with α,β-unsaturated carbonyl as well as hetero analogous carbonyl compounds such as acrylonitrile, suitable precursors of isofagomine and of 4-epi-isofagomine are available. Elaboration of the structures by amine introduction, followed by intramolecular ring closure and subsequent hydroboration of the double bond provides 4-epi-isofagomine derivatives featuring chain extensions at C-5a which are determined by the structures of the carbonyl compounds employed. As an example, the synthesis of C-(5aR)- and C-(5aS)-5a-C-pentyl-4-epi-isofagomines, powerful inhibitors of β-galactosidases, is outlined. In line with reported data, the (C-5aR) epimer was found a highly potent experimental pharmacological chaperone for GM1-associated human lysosomal β-galactosidase mutant R201C. Copyright © 2017 Elsevier Ltd. All rights reserved.
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Dose-Response Relationship, Drug -
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Glycoside Hydrolases - antagonists & inhibitors
Glycoside Hydrolases - metabolism
Humans -
Imino Pyranoses - chemical synthesis
Imino Pyranoses - chemistry
Imino Pyranoses - pharmacology
Lysosomes - enzymology
Molecular Structure -
Structure-Activity Relationship -

Find related publications in this database (Keywords)
Morita-Baylis-Hillman reaction
4-epi-isofagomine
Glycosidase inhibitor
Pharmacological chaperone
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