Research article summary (published 7 Feb 2009):

Silica-bound copper(II)triazacyclononane as a phosphate esterase: effect of linker length and surface hydrophobicity.

Full Abstract

A series of silica-bound Cu(ii) triazacyclononane materials was prepared to study the effect of linker length and surface hydrophobicity on the hydrolysis of phosphate esters. The general synthetic approach for these heterogeneous reagents was rhodium-catalyzed hydrosilation between an alkenyl-modified triazacyclononane and hydride-modified silica followed by metallation with a Cu(ii) salt. Elemental analysis confirmed that organic functionalization of the silica gel was successful and provided an estimate of the surface concentration of triazacyclononane. EPR spectra were consistent with square pyramidal Cu(ii), indicating that Cu(ii) ions were bound to the immobilized macrocycles. The hydrolytic efficacies of these heterogeneous reagents were tested with bis(p-nitrophenyl)phosphate (BNPP) and diethyl 4-nitrophenyl phosphate (paraoxon). The agent that performed best was an octyl-linked, propanol-blocked material. This material had the most hydrophilic surface and the most accessible active site, achieving a rate maximum on par with the other materials, but in fewer cycles and without an induction period.

Author information

Author/s: Bodsgard, Brett R (BR); Clark, Robert W (RW); Ehrbar, Anthony W (AW); Burstyn, Judith N (JN);

Affiliation: Department of Chemistry, Saint Mary's University of Minnesota, Winona, Minnesota 55987, USA.

Journal and publication information

Publication Type: Journal Article

Journal: Dalton transactions (Cambridge, England : 2003) (Dalton Trans), published in England. (Language: eng)

Reference: 2009-Apr; vol (issue 13) : pp 2365-73

Dates: Created 2009/03/17; Completed 2009/06/04;

PMID: 19290370, status: MEDLINE (last retrieved date: 6/4/2009)

Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.

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MeSH headings (categories)

This article was linked to the MeSH Headings (categories) shown below.

Copper - chemistry Esterases - chemistry Esters - chemistry Heterocyclic Compounds - chemistry Hydrolysis

Hydrophobicity Organometallic Compounds - chemical synthesis; chemistry Phosphates - chemistry Silicon Dioxide - chemistry Surface Properties

Note: Bold headings indicate primary MeSH headings or qualifiers.

Associated Chemicals: Esters (0) ; Heterocyclic Compounds (0) ; Organometallic Compounds (0) ; Phosphates (0) ; 1,4,7-triazacyclononane (4730-54-5) ; Copper (7440-50-8) ; Silicon Dioxide (7631-86-9) ; Esterases (EC 3.1.-)

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