Synthesis of modified 1,5‑imino‑d‑xylitols as ligands for lysosomal β‑glucocerebrosidase

Manuel Zoidl, Andreas Wolfsgruber, Michael Schalli, Seyed A. Nasseri, Patrick Weber, Arnold Stütz, S. G. Withers, Tanja Maria Wrodnigg

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Abstract: Modified 1,5-dideoxy-1,5-imino-d-xylitol analogues with different substitution patterns involving position C-1 and/or the ring nitrogen were prepared, which were designed to serve as precursors for the preparation of iminoxylitol-based ligands and tools for the elucidation and modulation of human lysosomal β-glucocerebrosidase. Biological evaluation of the synthesized glycomimetics with a series of glycoside hydrolases revealed that these substitution patterns elicit excellent β-glucosidase selectivities. Graphical abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)831-842
Number of pages12
JournalMonatshefte für Chemie = Chemical monthly
Volume150
Issue number5
DOIs
Publication statusPublished - 2019

Keywords

  • Carbohydrates
  • Conformation
  • Enzymes
  • Iminoxylitol
  • β-Glucocerebrosidase
  • β-Glucosidase ligands
  • -Glucocerebrosidase
  • -Glucosidase ligands

ASJC Scopus subject areas

  • Chemistry(all)

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