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

TY - JOUR

T1 - Synthesis of potential metal-binding group compounds to examine the zinc dependency of the GPI de-N-acetylase metalloenzyme in Trypanosoma brucei

AU - Abdelwahab, Nuha Z.

AU - Urbaniak, Michael D.

AU - Ferguson, Michael A. J.

AU - Crossman, Arthur T.

PY - 2011/5/1

Y1 - 2011/5/1

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

U2 - 10.1016/j.carres.2011.02.004

DO - 10.1016/j.carres.2011.02.004

M3 - Article

C2 - 21377660

SN - 0008-6215

VL - 346

SP - 708

EP - 714

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 6

ER -