N-alkylated iminosugar based ligands: Synthesis and inhibition of human lysosomal β-glucocerebrosidase

Andreas Wolfsgruber, Martin Thonhofer, Patrick Weber, Seyed A. Nasseri, Roland Fischer, Michael Schalli, Arnold E. Stütz, Stephen G. Withers, Tanja M. Wrodnigg*

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

The scope of a series of N-alkylated iminosugar based inhibitors in the d-gluco as well as d-xylo configuration towards their interaction with human lysosomal β-glucocerebrosidase has been evaluated. A versatile synthetic toolbox has been developed for the synthesis of N-alkylated iminosugar scaffolds conjugated to a variety of terminal groups via a benzoic acid ester linker. The terminal groups such as nitrile, azide, alkyne, nonafluoro-tert-butyl and amino substituents enable follow-up chemistry as well as visualisation experiments. All compounds showed promising inhibitory properties as well as selectivities for β-glucosidases, some exhibiting activities in the low nanomolar range for β-glucocerebrosidase.
Originalspracheenglisch
Aufsatznummer4618
FachzeitschriftMolecules
Jahrgang25
Ausgabenummer20
DOIs
PublikationsstatusVeröffentlicht - Okt 2020

ASJC Scopus subject areas

  • Analytische Chemie
  • !!Chemistry (miscellaneous)
  • !!Molecular Medicine
  • !!Pharmaceutical Science
  • !!Drug Discovery
  • !!Physical and Theoretical Chemistry
  • Organische Chemie

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