Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei

Nuha Z. Abdelwahab; Michael D. Urbaniak; Michael A. J. Ferguson; Arthur T. Crossman

doi:10.1016/j.carres.2011.02.004

Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei

Nuha Z. Abdelwahab, Michael D. Urbaniak, Michael A. J. Ferguson, Arthur T. Crossman

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

A small zinc-binding group (ZBG) library of deoxy-2-C-branched-monosaccharides, for example, 1,5-anhydroglucitols, consisting of either monodentate ligand binding carboxylic acids or bidentate ligand binding hydroxamic acids, were prepared to assess the zinc affinity of the putative metalloenzyme 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 6)-phosphatidylinositol de-N-acetylase (EC 3.5.1.89) of glycosylphosphatidylinositol biosynthesis. The N-ureido thioglucoside was also synthesised and added to the ZBG library because a previous N-ureido analogue, synthesised by us, had inhibitory activity against the aforementioned de-N-acetylase, presumably via the N-ureido motif. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	708-714
Number of pages	7
Journal	Carbohydrate Research
Volume	346
Issue number	6
DOIs	https://doi.org/10.1016/j.carres.2011.02.004
Publication status	Published - 1 May 2011

Keywords

Glycosylphosphatidylinositol (GPI) biosynthesis
Zinc metalloenzyme inhibitor
Zinc-binding group
Branched monosaccharides, Phosphatidylinositol de-N-acetylase
AFRICAN SLEEPING SICKNESS
GLYCOSYLPHOSPHATIDYLINOSITOL BIOSYNTHESIS
INOSITOL ACYLATION
ANCHORED PROTEINS
MEMBRANE ANCHOR
INHIBITORS
2-AMINO-2-DEOXY-D-GLUCOSE
SPECIFICITY
DERIVATIVES
OXIDATION

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.carres.2011.02.004

Aref#d: 20731. The Biosynthesis of Glycoproteins in Trypanosoma Brucei: Basic and Translational Research
Ferguson, M. (Investigator) & Gilbert, I. (Investigator)
1/10/08 → 31/05/14
Project: Research

Cite this

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title = "Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei",

abstract = "A small zinc-binding group (ZBG) library of deoxy-2-C-branched-monosaccharides, for example, 1,5-anhydroglucitols, consisting of either monodentate ligand binding carboxylic acids or bidentate ligand binding hydroxamic acids, were prepared to assess the zinc affinity of the putative metalloenzyme 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 6)-phosphatidylinositol de-N-acetylase (EC 3.5.1.89) of glycosylphosphatidylinositol biosynthesis. The N-ureido thioglucoside was also synthesised and added to the ZBG library because a previous N-ureido analogue, synthesised by us, had inhibitory activity against the aforementioned de-N-acetylase, presumably via the N-ureido motif. (C) 2011 Elsevier Ltd. All rights reserved.",

keywords = "Glycosylphosphatidylinositol (GPI) biosynthesis, Zinc metalloenzyme inhibitor, Zinc-binding group, Branched monosaccharides, Phosphatidylinositol de-N-acetylase, AFRICAN SLEEPING SICKNESS, GLYCOSYLPHOSPHATIDYLINOSITOL BIOSYNTHESIS, INOSITOL ACYLATION, ANCHORED PROTEINS, MEMBRANE ANCHOR, INHIBITORS, 2-AMINO-2-DEOXY-D-GLUCOSE, SPECIFICITY, DERIVATIVES, OXIDATION",

author = "Abdelwahab, {Nuha Z.} and Urbaniak, {Michael D.} and Ferguson, {Michael A. J.} and Crossman, {Arthur T.}",

year = "2011",

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doi = "10.1016/j.carres.2011.02.004",

language = "English",

volume = "346",

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journal = "Carbohydrate Research",

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AU - Abdelwahab, Nuha Z.

AU - Urbaniak, Michael D.

AU - Ferguson, Michael A. J.

AU - Crossman, Arthur T.

PY - 2011/5/1

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N2 - A small zinc-binding group (ZBG) library of deoxy-2-C-branched-monosaccharides, for example, 1,5-anhydroglucitols, consisting of either monodentate ligand binding carboxylic acids or bidentate ligand binding hydroxamic acids, were prepared to assess the zinc affinity of the putative metalloenzyme 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 6)-phosphatidylinositol de-N-acetylase (EC 3.5.1.89) of glycosylphosphatidylinositol biosynthesis. The N-ureido thioglucoside was also synthesised and added to the ZBG library because a previous N-ureido analogue, synthesised by us, had inhibitory activity against the aforementioned de-N-acetylase, presumably via the N-ureido motif. (C) 2011 Elsevier Ltd. All rights reserved.

AB - A small zinc-binding group (ZBG) library of deoxy-2-C-branched-monosaccharides, for example, 1,5-anhydroglucitols, consisting of either monodentate ligand binding carboxylic acids or bidentate ligand binding hydroxamic acids, were prepared to assess the zinc affinity of the putative metalloenzyme 2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 -> 6)-phosphatidylinositol de-N-acetylase (EC 3.5.1.89) of glycosylphosphatidylinositol biosynthesis. The N-ureido thioglucoside was also synthesised and added to the ZBG library because a previous N-ureido analogue, synthesised by us, had inhibitory activity against the aforementioned de-N-acetylase, presumably via the N-ureido motif. (C) 2011 Elsevier Ltd. All rights reserved.

KW - Glycosylphosphatidylinositol (GPI) biosynthesis

KW - Zinc metalloenzyme inhibitor

KW - Zinc-binding group

KW - Branched monosaccharides, Phosphatidylinositol de-N-acetylase

KW - AFRICAN SLEEPING SICKNESS

KW - GLYCOSYLPHOSPHATIDYLINOSITOL BIOSYNTHESIS

KW - INOSITOL ACYLATION

KW - ANCHORED PROTEINS

KW - MEMBRANE ANCHOR

KW - INHIBITORS

KW - 2-AMINO-2-DEOXY-D-GLUCOSE

KW - SPECIFICITY

KW - DERIVATIVES

KW - OXIDATION

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DO - 10.1016/j.carres.2011.02.004

M3 - Article

C2 - 21377660

SN - 0008-6215

VL - 346

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JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 6

ER -

Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei

Abstract

Keywords

UN SDGs

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Projects

Aref#d: 20731. The Biosynthesis of Glycoproteins in Trypanosoma Brucei: Basic and Translational Research

Cite this