Oxidase–peroxidase reaction: kinetics of peroxidase-catalysed oxidation of 2-aminophenol

Puiu, Mihaela; Răducan, Adina; Babaligea, Irina; Oancea, Dumitru

doi:10.1007/s00449-008-0206-8

Cited by 17 publications

(7 citation statements)

References 42 publications

(74 reference statements)

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“…The monomer o -aminophenol can easily be transformed to its dimer 2-amino-3 H -phenoxazin-3-one via enzymatic oxidation followed by oxidative cyclization, e.g., using HRP (Puiu et al 2008). Fungal laccases as green catalysts for the synthesis of various colored products, including phenoxazinone-based dyes, have recently been reviewed by Polak and Jarosz-Wilkolazka (2012).…”

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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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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“…UV-vis spectra of those products showed a double peak at the wavelengths of 420 to 440 nm (Figure 3A, 3B). Fungal-mediated conversion of AHBS yielded a product with a typical UV-vis spectrum characteristic of phenoxazinone-type compounds, and laccase was shown to be responsible for this biotransformation [6-9,29-32]. …”

Section: Resultsmentioning

confidence: 99%

Whole-cell fungal transformation of precursors into dyes

Polak

Jarosz-Wilkołazka

2010

Microb Cell Fact

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BackgroundChemical methods of producing dyes involve extreme temperatures and unsafe toxic compounds. Application of oxidizing enzymes obtained from fungal species, for example laccase, is an alternative to chemical synthesis of dyes. Laccase can be replaced by fungal biomass acting as a whole-cell biocatalyst with properties comparable to the isolated form of the enzyme. The application of the whole-cell system simplifies the transformation process and reduces the time required for its completion. In the present work, four fungal strains with a well-known ability to produce laccase were tested for oxidation of 17 phenolic and non-phenolic precursors into stable and non-toxic dyes.ResultsAn agar-plate screening test of the organic precursors was carried out using four fungal strains: Trametes versicolor, Fomes fomentarius, Abortiporus biennis, and Cerrena unicolor. Out of 17 precursors, nine were transformed into coloured substances in the presence of actively growing fungal mycelium. The immobilized fungal biomass catalyzed the transformation of 1 mM benzene and naphthalene derivatives in liquid cultures yielding stable and non-toxic products with good dyeing properties. The type of fungal strain had a large influence on the absorbance of the coloured products obtained after 48-hour transformation of the selected precursors, and the most effective was Fomes fomentarius (FF25). Whole-cell transformation of AHBS (3-amino-4-hydroxybenzenesulfonic acid) into a phenoxazinone dye was carried out in four different systems: in aqueous media comprising low amounts of carbon and nitrogen source, in buffer, and in distilled water.ConclusionsThis study demonstrated the ability of four fungal strains belonging to the ecological type of white rot fungi to transform precursors into dyes. This paper highlights the potential of fungal biomass for replacing isolated enzymes as a cheaper industrial-grade biocatalyst for the synthesis of dyes and other commercially important products. The use of immobilized fungal biomass limits free migration of cells and facilitates their reuse in a continuous system for precursor transformation.

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“…In the absence of reducing substrates, an excess of H 2 O 2 leads to inactivation of the enzyme, in this case the H 2 O 2 acting as a suicide substrate of peroxidase and being irreversibly bound to its active site [4,5]. However, it has been suggested by several authors [6,7] that the HRP inactivation by hydrogen peroxide is due to the formation of one or several non-active enzyme products likely through the formation of Compound III (peroxyl-FeIII porphyrin).…”

Section: Introductionmentioning

confidence: 95%