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

Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

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.].

Originalspracheenglisch
Seiten (von - bis)831-842
Seitenumfang12
FachzeitschriftMonatshefte für Chemie = Chemical monthly
Jahrgang150
Ausgabenummer5
DOIs
PublikationsstatusVeröffentlicht - 2019

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Glucosylceramidase
Substitution reactions
Glucosidases
Ligands
Xylitol
Glycoside Hydrolases
Nitrogen
Modulation

Schlagwörter

    ASJC Scopus subject areas

    • !!Chemistry(all)

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    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, Jahrgang 150, Nr. 5, 2019, S. 831-842.

    Publikation: Beitrag in einer FachzeitschriftArtikelForschungBegutachtung

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    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.].",
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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

    PY - 2019

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    N2 - 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.].

    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.].

    KW - Carbohydrates

    KW - Conformation

    KW - Enzymes

    KW - Iminoxylitol

    KW - β-Glucocerebrosidase

    KW - β-Glucosidase ligands

    KW - -Glucocerebrosidase

    KW - -Glucosidase ligands

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    JO - Monatshefte für Chemie = Chemical monthly

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