Oxidative coupling of various aromatic phenols and anilines in water using a laccase from <i>Trametes villosa</i> and insights into the ‘PEG effect’

Steevensz, Aaron; Al-Ansari, Mohammad Mousa; Taylor, Keith E.; Bewtra, Jatinder K.; Biswas, Nihar

doi:10.1002/jctb.2734

Cited by 14 publications

(19 citation statements)

References 59 publications

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“…It can be seen in Fig. 3 that PEG had no effect on the SBP treatment of aniline, this is similar to findings by Patapas et al (2007), in which they found the addition of PEG had no effect on Arthromyces ramosus peroxidase treatment of aniline, as well as a study by Steevensz et al (2012) that found no PEG effect in the treatment of aniline with laccase. All other additives showed improvement of enzymatic treatment after their addition, with SDOD having the most significant impact.…”

Section: Additive Effect On Sbp Treatment Of Aniline and O-anisidinesupporting

confidence: 86%

Additive Effect on Soybean Peroxidase-Catalyzed Removal of Anilines from Water

Mazloum

Al-Ansari

Taylor

et al. 2016

Environmental Engineering Science

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Soybean peroxidase has been shown to be effective in removal of aromatic compounds from wastewater, while the use of additives effectively reduces enzyme concentration requirement, hence overall treatment cost. Enzymatic treatment, an oxidative polymerization, was successful in removal of over 95% of both aniline and oanisidine. The originality of this study lies in the findings that the additives, sodium dodecyl sulfate (SDS), sodium dodecylbenzenesulfonate (SDBS), Triton X-100, and sodium dodecanoate (SDOD), reduced enzyme concentration requirement, while polyethylene glycol (PEG, average molar mass of 3350 g/mol) had no effect on the required enzyme concentration. In addition, the presence of SDS also enhanced treatment by improving precipitation and color removal. These results are enabling advancement of soybean peroxidase-catalyzed treatment of anilines found in wastewaters as a new sustainable method.

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Section: Additive Effect On Sbp Treatment Of Aniline and O-anisidinesupporting

confidence: 86%

Additive Effect on Soybean Peroxidase-Catalyzed Removal of Anilines from Water

Mazloum

Al-Ansari

Taylor

et al. 2016

Environmental Engineering Science

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“…The enzymatic oxidative coupling of o -, m -, and p -toluidine to the corresponding low-molecular-weight soluble orange-brown to purple-brown colored oligomers was achieved using laccase from Trametes villosa in the presence of poly(ethylene glycol) (Steevensz et al 2012). The oxidative oligomerization of p -anisidine by H 2 O 2 catalyzed by peroxidase was examined by Daniels and Saunders (1951).…”

Section: Enzymatic Oligomerization Of Arylaminesmentioning

confidence: 99%

Enzymatic oligomerization and polymerization of arylamines: state of the art and perspectives

et al. 2016

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The literature concerning the oxidative oligomerization and polymerization of various arylamines, e.g., aniline, substituted anilines, aminonaphthalene and its derivatives, catalyzed by oxidoreductases, such as laccases and peroxidases, in aqueous, organic, and mixed aqueous organic monophasic or biphasic media, is reviewed. An overview of template-free as well as template-assisted enzymatic syntheses of oligomers and polymers of arylamines is given. Special attention is paid to mechanistic aspects of these biocatalytic processes. Because of the nontoxicity of oxidoreductases and their high catalytic efficiency, as well as high selectivity of enzymatic oligomerizations/polymerizations under mild conditions—using mainly water as a solvent and often resulting in minimal byproduct formation—enzymatic oligomerizations and polymerizations of arylamines are environmentally friendly and significantly contribute to a “green” chemistry of conducting and redox-active oligomers and polymers. Current and potential future applications of enzymatic polymerization processes and enzymatically synthesized oligo/polyarylamines are discussed.

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“…Steevensz et al. showed that PEG extended the lifetime conversion of the phenolics into polymers . If a “PEG effect” was observed, there was a linear relationship between the amount of additive used and the amount of precipitate, suggesting a strong interaction between products and PEG, confirmed by NMR spectroscopy.…”

Section: Introductionmentioning

confidence: 97%

“…These enzymes are mostly considered as extracellular proteins that are fairly stable if kept at neutral pH and under room temperature, with a broad substrate specificity, catalytic activity, effective pH range, and working temperature range. They have received much attention for their potential use in a wide variety of applications such as biosensors, bioremediation, green synthesis, green biodegradation of xenobiotics, and other areas …”

Section: Introductionmentioning

confidence: 99%

“…These authors also studied the enzymatic oxidative polymerization of phenol by the addition of poly(ethylene glycol) monododecyl ether (PEGMDE) template to the medium. They observed that the addition of this additive pushed forward the polymerization in water . The presence of PEGMDE template in the aqueous medium greatly improved the regioselectivity, yielding polyphenol with a phenylene unit content near 90 %.…”

Section: Introductionmentioning

confidence: 99%

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PEGylation Greatly Enhances Laccase Polymerase Activity

Noro

Loureiro

et al. 2017

ChemCatChem

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Laccase catalyzes the oxidation and polymerization of phenolic compounds in the presence of oxygen. Herein, we report for the first time that a previous PEGylation of laccase enhances the polymerase activity 3‐fold compared with the reaction of the native enzyme, as confirmed by UV/Vis spectroscopy. The polymerization of catechol increased only 1.5‐fold if poly(ethylene glycol) (PEG) was added to the medium reaction. Molecular‐dynamics simulations suggest the formation of a miscible complex of polycatechol and PEG, which is responsible to push the reaction forward. In a negative control experiment set, all catalysts were entrapped inside polyacrylamide gels and here the native laccase showed a relatively higher activity. These results suggest that the mobility of PEG is a key feature for the enhancement of the reaction.

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Oxidative coupling of various aromatic phenols and anilines in water using a laccase from Trametes villosa and insights into the ‘PEG effect’

Cited by 14 publications

References 59 publications

Additive Effect on Soybean Peroxidase-Catalyzed Removal of Anilines from Water

Additive Effect on Soybean Peroxidase-Catalyzed Removal of Anilines from Water

Enzymatic oligomerization and polymerization of arylamines: state of the art and perspectives

PEGylation Greatly Enhances Laccase Polymerase Activity

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