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

Patrick Weber; Seyed A. Nasseri; Bettina M. Pabst; Ana Torvisco; Philipp Müller; Eduard Paschke; Marion Tschernutter; Werner Windischhofer; Stephen G. Withers; Tanja M. Wrodnigg; Arnold E. Stütz

doi:10.3390/molecules23030708

Molecules (Mar 2018)

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

Patrick Weber,
Seyed A. Nasseri,
Bettina M. Pabst,
Ana Torvisco,
Philipp Müller,
Eduard Paschke,
Marion Tschernutter,
Werner Windischhofer,
Stephen G. Withers,
Tanja M. Wrodnigg,
Arnold E. Stütz

Affiliations

Patrick Weber: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
Seyed A. Nasseri: Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
Bettina M. Pabst: Laboratory of Metabolic Diseases, Department of Pediatrics, MedUni Graz, Auenbruggerplatz 30, A-8036 Graz, Austria
Ana Torvisco: Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
Philipp Müller: Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
Eduard Paschke: Laboratory of Metabolic Diseases, Department of Pediatrics, MedUni Graz, Auenbruggerplatz 30, A-8036 Graz, Austria
Marion Tschernutter: Laboratory of Metabolic Diseases, Department of Pediatrics, MedUni Graz, Auenbruggerplatz 30, A-8036 Graz, Austria
Werner Windischhofer: Laboratory of Metabolic Diseases, Department of Pediatrics, MedUni Graz, Auenbruggerplatz 30, A-8036 Graz, Austria
Stephen G. Withers: Chemistry Department, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
Tanja M. Wrodnigg: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria
Arnold E. Stütz: Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 9, A-8010 Graz, Austria

DOI: https://doi.org/10.3390/molecules23030708
Journal volume & issue: Vol. 23, no. 3
p. 708

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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