Phenol Conversion and Dimeric Intermediates in Horseradish Peroxidase-Catalyzed Phenol Removal from Water

Yu, Jianguo; Taylor, Keith E.; Zou, Huixian.; Biswas, Nihar; Bewtra, Jatinder K.

doi:10.1021/es00061a025

Cited by 130 publications

(96 citation statements)

References 16 publications

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“…When the nanocomplex, H 2 O 2 and phenol were mixed, the solution readily turned dark brown (Fig. 6), a phenomenon resembling that observed with HRP [13,26]. We ascribe this phenol oxidation to a similar mechanism to that reported for HRP-mediated phenol degradation [26], which is shown as follows ("m" stands for an activated state of the nanocomplex, Ph • for the phenoxy radical and Ph-Ph for the dimeric product).…”

Section: Resultssupporting

confidence: 58%

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Design of a carbon nanotube/magnetic nanoparticle-based peroxidase-like nanocomplex and its application for highly efficient catalytic oxidation of phenols

et al. 2009

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We report a novel nanotechnology-based approach for the highly efficient catalytic oxidation of phenols and their removal from wastewater. We use a nanocomplex made of multi-walled carbon nanotubes (MWNTs) and magnetic nanoparticles (MNPs). This nanocomplex retains the magnetic properties of individual MNPs and can be effectively separated under an external magnetic fi eld. More importantly, the formation of the nanocomplex enhances the intrinsic peroxidase-like activity of the MNPs that can catalyze the reduction of hydrogen peroxide (H 2 O 2 ). Significantly, in the presence of H 2 O 2 , this nanocomplex catalyzes the oxidation of phenols with high effi ciency, generating insoluble polyaromatic products that can be readily separated from water.

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Section: Resultssupporting

confidence: 58%

“…HRP oxidizes phenols to phenoxy radicals that polymerize phenols into insoluble polyaromatic products [13,26]. When the nanocomplex, H 2 O 2 and phenol were mixed, the solution readily turned dark brown (Fig.…”

Section: Resultsmentioning

confidence: 99%

Design of a carbon nanotube/magnetic nanoparticle-based peroxidase-like nanocomplex and its application for highly efficient catalytic oxidation of phenols

et al. 2009

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“…The application of plant and microorganism peroxidases to catalyze the polymerization and precipitation of aqueous phenols and decolourization of bleach plant effluent by hydrogen peroxide is potentially promising, because PODs from new sources are less expensive than horseradish peroxidase (16), which has been the focus of most wastewater research.…”

Section: Introductionmentioning

confidence: 99%

Purification and enzymatic properties of a peroxidase from leaves of Phytolacca dioica L. (Ombú tree)

Guida¹,

Criscuolo²,

Tamburino³

et al. 2011

BMB Reports

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“…Yu et al 1994 i dentified five dimeric and one trimeric products from the reaction aqueous solution. He further concluded that the two monophenoxy radicals are likely to couple at the oxygen, ortho and para atoms of a molecular based on t he detection of their high unpaired electron densities.…”

Section: Kinetic Study and Product Identificationmentioning

confidence: 99%

Chemical kinetics and interactions involved in horseradish peroxidase-mediated oxidative polymerization of phenolic compounds

Cheng

Harper

2012

Enzyme and Microbial Technology

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iv To address the growing need for removing the emerging endocrine disrupting compounds (EDCs), the enzyme-based oxidative coupling reaction is suggested as promising alternative in consideration of its generally high specificity and removal efficiency on treatment of waters containing estrogenic phenolic chemicals.Various factors that affect the reaction rate of oxidative coupling (OXC) reaction of phenolic estrogens catalyzed by Horseradish Peroxidase (HRP) were evaluated in this study. Kinetic parameters were obtained for the removal of phenol as well as natural and synthetic estrogens estrone (E 1 ), 17β-estradiol (E 2 ), estriol (E 3 ), and 17α-ethinylestradiol (EE 2 ). Molecular orbital theory and Autodock software were employed to analyze chemical properties and substrate binding characteristics. It is found that the reactions were first order with respect to phenolic concentration and reaction rate constants (k r ) were determined for phenol, E 3 , E 1 , E 2 and EE 2 (in increasing order). It is also found that oxidative coupling was controlled by enzyme-substrate interactions, not diffusion. Docking simulations show that higher binding energy and shorter binding distance both promote more favorable kinetics. This research is the first to show that the OXC of phenolics is an entropy-driven and enthalpy-retarded process.

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Phenol Conversion and Dimeric Intermediates in Horseradish Peroxidase-Catalyzed Phenol Removal from Water

Cited by 130 publications

References 16 publications

Design of a carbon nanotube/magnetic nanoparticle-based peroxidase-like nanocomplex and its application for highly efficient catalytic oxidation of phenols

Design of a carbon nanotube/magnetic nanoparticle-based peroxidase-like nanocomplex and its application for highly efficient catalytic oxidation of phenols

Purification and enzymatic properties of a peroxidase from leaves of Phytolacca dioica L. (Ombú tree)

Chemical kinetics and interactions involved in horseradish peroxidase-mediated oxidative polymerization of phenolic compounds

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