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.].

LanguageEnglish
Pages831-842
Number of pages12
JournalMonatshefte für Chemie = Chemical monthly
Volume150
Issue number5
DOIs
StatusPublished - 2019

Fingerprint

Glucosylceramidase
Xylitol
Substitution reactions
Ligands
beta-Glucosidase
Glycoside Hydrolases
Nitrogen
Modulation

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of modified 1,5‑imino‑d‑xylitols as ligands for lysosomal β‑glucocerebrosidase. / Zoidl, Manuel; Wolfsgruber, Andreas; Schalli, Michael; Nasseri, Seyed A.; Weber, Patrick; Stütz, Arnold; Withers, S. G.; Wrodnigg, Tanja Maria .

In: Monatshefte für Chemie = Chemical monthly, Vol. 150, No. 5, 2019, p. 831-842.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Zoidl, Manuel

AU - Wolfsgruber, Andreas

AU - Schalli, Michael

AU - Nasseri, Seyed A.

AU - Weber, Patrick

AU - Stütz, Arnold

AU - Withers, S. G.

AU - Wrodnigg, Tanja Maria

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AB - 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.].

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