A structural and catalytic model for zinc phosphoesterases

Rebecca R. Buchholz; Morgan E. Etienne; Anneke Dorgelo; Ruth E. Mirams; Sarah J. Smith; Shiao Yun Chow; Lyall R. Hanton; Geoffrey B. Jameson; Gerhard Schenk; Lawrence R. Gahan

doi:10.1039/b806391e

A structural and catalytic model for zinc phosphoesterases

Rebecca R. Buchholz, Morgan E. Etienne, Anneke Dorgelo, Ruth E. Mirams, Sarah J. Smith, Shiao Yun Chow, Lyall R. Hanton, Geoffrey B. Jameson, Gerhard Schenk, Lawrence R. Gahan

Atmospheric Composition Remote Sensing and Prediction

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Abstract

A structural model for the active site of phosphoesterases, enzymes that degrade organophosphate neurotoxins, has been synthesised. The ligand [2-((2-hydroxy-3-(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl) -5-methylbenzyl)(pyridin-2-ylmethyl)amino)acetic acid] (H₃L1) and two Zn(ii) complexes have been prepared and characterised as [Zn ₂(HL1)(CH₃COO)](PF₆)·H₂O and Li[Zn₂(HL1)]₄(PO₄)₂(PF ₆)₃·(CH₃OH). The ligand (H ₃L1) and complex [Zn₂(HL1)(CH₃COO)](PF ₆)·H₂O were characterised through ¹H NMR, ¹³C NMR, mass spectroscopy and microanalysis. The X-ray crystal structure of Li[Zn₂(HL1)]₄(PO₄) ₂(PF₆)₃·(CH₃OH) revealed a tetramer of dinuclear complexes, bridged by two phosphate molecules and bifurcating acetic acid arms. Functional studies of the zinc complex with the substrate bis(4-nitrophenyl)phosphate (bNPP) determined the complex with HL1^2- to be a competent catalyst with k_cat = 1.26 ± 0.06 × 10^-6 s^-1.

Original language	English
Pages (from-to)	6045-6054
Number of pages	10
Journal	Dalton Transactions
Issue number	43
DOIs	https://doi.org/10.1039/b806391e
State	Published - 2008

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@article{368d52692f934cc4ba7440838f84fe8d,

title = "A structural and catalytic model for zinc phosphoesterases",

abstract = "A structural model for the active site of phosphoesterases, enzymes that degrade organophosphate neurotoxins, has been synthesised. The ligand [2-((2-hydroxy-3-(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl) -5-methylbenzyl)(pyridin-2-ylmethyl)amino)acetic acid] (H3L1) and two Zn(ii) complexes have been prepared and characterised as [Zn 2(HL1)(CH3COO)](PF6)·H2O and Li[Zn2(HL1)]4(PO4)2(PF 6)3·(CH3OH). The ligand (H 3L1) and complex [Zn2(HL1)(CH3COO)](PF 6)·H2O were characterised through 1H NMR, 13C NMR, mass spectroscopy and microanalysis. The X-ray crystal structure of Li[Zn2(HL1)]4(PO4) 2(PF6)3·(CH3OH) revealed a tetramer of dinuclear complexes, bridged by two phosphate molecules and bifurcating acetic acid arms. Functional studies of the zinc complex with the substrate bis(4-nitrophenyl)phosphate (bNPP) determined the complex with HL12- to be a competent catalyst with kcat = 1.26 ± 0.06 × 10-6 s-1.",

author = "Buchholz, \{Rebecca R.\} and Etienne, \{Morgan E.\} and Anneke Dorgelo and Mirams, \{Ruth E.\} and Smith, \{Sarah J.\} and Chow, \{Shiao Yun\} and Hanton, \{Lyall R.\} and Jameson, \{Geoffrey B.\} and Gerhard Schenk and Gahan, \{Lawrence R.\}",

year = "2008",

doi = "10.1039/b806391e",

language = "English",

pages = "6045--6054",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "43",

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T1 - A structural and catalytic model for zinc phosphoesterases

AU - Buchholz, Rebecca R.

AU - Etienne, Morgan E.

AU - Dorgelo, Anneke

AU - Mirams, Ruth E.

AU - Smith, Sarah J.

AU - Chow, Shiao Yun

AU - Hanton, Lyall R.

AU - Jameson, Geoffrey B.

AU - Schenk, Gerhard

AU - Gahan, Lawrence R.

PY - 2008

Y1 - 2008

N2 - A structural model for the active site of phosphoesterases, enzymes that degrade organophosphate neurotoxins, has been synthesised. The ligand [2-((2-hydroxy-3-(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl) -5-methylbenzyl)(pyridin-2-ylmethyl)amino)acetic acid] (H3L1) and two Zn(ii) complexes have been prepared and characterised as [Zn 2(HL1)(CH3COO)](PF6)·H2O and Li[Zn2(HL1)]4(PO4)2(PF 6)3·(CH3OH). The ligand (H 3L1) and complex [Zn2(HL1)(CH3COO)](PF 6)·H2O were characterised through 1H NMR, 13C NMR, mass spectroscopy and microanalysis. The X-ray crystal structure of Li[Zn2(HL1)]4(PO4) 2(PF6)3·(CH3OH) revealed a tetramer of dinuclear complexes, bridged by two phosphate molecules and bifurcating acetic acid arms. Functional studies of the zinc complex with the substrate bis(4-nitrophenyl)phosphate (bNPP) determined the complex with HL12- to be a competent catalyst with kcat = 1.26 ± 0.06 × 10-6 s-1.

AB - A structural model for the active site of phosphoesterases, enzymes that degrade organophosphate neurotoxins, has been synthesised. The ligand [2-((2-hydroxy-3-(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl) -5-methylbenzyl)(pyridin-2-ylmethyl)amino)acetic acid] (H3L1) and two Zn(ii) complexes have been prepared and characterised as [Zn 2(HL1)(CH3COO)](PF6)·H2O and Li[Zn2(HL1)]4(PO4)2(PF 6)3·(CH3OH). The ligand (H 3L1) and complex [Zn2(HL1)(CH3COO)](PF 6)·H2O were characterised through 1H NMR, 13C NMR, mass spectroscopy and microanalysis. The X-ray crystal structure of Li[Zn2(HL1)]4(PO4) 2(PF6)3·(CH3OH) revealed a tetramer of dinuclear complexes, bridged by two phosphate molecules and bifurcating acetic acid arms. Functional studies of the zinc complex with the substrate bis(4-nitrophenyl)phosphate (bNPP) determined the complex with HL12- to be a competent catalyst with kcat = 1.26 ± 0.06 × 10-6 s-1.

UR - https://www.scopus.com/pages/publications/55149118943

U2 - 10.1039/b806391e

DO - 10.1039/b806391e

M3 - Article

C2 - 19082062

AN - SCOPUS:55149118943

SN - 1477-9226

SP - 6045

EP - 6054

JO - Dalton Transactions

JF - Dalton Transactions

IS - 43

ER -

A structural and catalytic model for zinc phosphoesterases

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