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

doi:10.1007/s00706-019-02427-1

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

Institute of Organic Chemistry (6410)

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	831-842
Number of pages	12
Journal	Monatshefte für Chemie - Chemical Monthly
Volume	150
Issue number	5
DOIs	https://doi.org/10.1007/s00706-019-02427-1
Publication status	Published - 2019

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

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10.1007/s00706-019-02427-1

Cite this

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

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.].",

keywords = "Carbohydrates, Conformation, Enzymes, Iminoxylitol, β-Glucocerebrosidase, β-Glucosidase ligands, -Glucocerebrosidase, -Glucosidase ligands",

author = "Manuel Zoidl and Andreas Wolfsgruber and Michael Schalli and Nasseri, {Seyed A.} and Patrick Weber and Arnold St{\"u}tz and Withers, {S. G.} and Wrodnigg, {Tanja Maria}",

year = "2019",

doi = "10.1007/s00706-019-02427-1",

language = "English",

volume = "150",

pages = "831--842",

journal = "Monatshefte f{\"u}r Chemie - Chemical Monthly",

issn = "0026-9247",

publisher = "Springer Wien",

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}

TY - JOUR

T1 - Synthesis of modified 1,5‑imino‑d‑xylitols as ligands for lysosomal β‑glucocerebrosidase

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

Y1 - 2019

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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U2 - 10.1007/s00706-019-02427-1

DO - 10.1007/s00706-019-02427-1

M3 - Article

SN - 0026-9247

VL - 150

SP - 831

EP - 842

JO - Monatshefte für Chemie - Chemical Monthly

JF - Monatshefte für Chemie - Chemical Monthly

IS - 5

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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