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Molecules 2018, 23(3), 708; https://doi.org/10.3390/molecules23030708

Potent GH20 N-Acetyl-β-d-hexosaminidase Inhibitors: N-Substituted 3-acetamido-4-amino-5-hydroxymethyl-cyclopentanediols

1
Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
2
Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
3
Laboratory of Metabolic Diseases, Department of Pediatrics, MedUni Graz, Auenbruggerplatz 30, A-8036 Graz, Austria
4
Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
*
Author to whom correspondence should be addressed.
Received: 28 February 2018 / Revised: 15 March 2018 / Accepted: 16 March 2018 / Published: 20 March 2018
(This article belongs to the Special Issue Glycomimetics: Design, Synthesis and Therapeutic Applications)
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Abstract

From 1,2;3,4-di-O-isopropylidene-d-galactopyranose, a preliminary series of highly functionalized amino(hydroxymethyl)cyclopentanes was easily available. These amine-containing basic carbasugars featuring the d-galacto configuration are potent inhibitors of the GH20 β-d-hexosaminidases probed and may bear potential as regulators of N-acetyl-d-hexosaminidase activities in vivo. View Full-Text
Keywords: aminocyclopentane; N-acetyl-d-hexosaminidase inhibitor; Tay-Sachs aminocyclopentane; N-acetyl-d-hexosaminidase inhibitor; Tay-Sachs
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Weber, P.; Nasseri, S.A.; Pabst, B.M.; Torvisco, A.; Müller, P.; Paschke, E.; Tschernutter, M.; Windischhofer, W.; Withers, S.G.; Wrodnigg, T.M.; Stütz, A.E. Potent GH20 N-Acetyl-β-d-hexosaminidase Inhibitors: N-Substituted 3-acetamido-4-amino-5-hydroxymethyl-cyclopentanediols. Molecules 2018, 23, 708.

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