Abstract
The enzymatic polymerization of phenolic compounds arouses more and more interest in the several fields such as food, cosmetic and pharmaceutical. The use of these compounds for their antioxidant properties is limited by their low solubility and thermal stability. The polymerization reaction improves their solubility and/or their thermal stability and provides new properties. These properties are dependent on the molecular mass and the structure of polymers. The reaction yield, the polydispersity, the molecular mass, the structure and thus the properties of synthesized polymers can be controlled by the mode of control of the reaction and by the reactional conditions. In this book, we analyze the key factors (temperature, solvent, origin of the enzyme, structure of the substrate, reactor design,…) who control the polymerization of phenolic compounds by the oxidoreductase enzymes, to obtain polymers with desired characteristics and properties.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Abou El Hassan MAI, Touw DJ, Wilhelm AJ et al (2000) Stability of monoHER in an aqueous formulation for i.v. administration. Int J Pharm 211:51–56
Afanas, rsquo, eva IB et al (2001) Enhancement of antioxidant and anti-inflammatory activities of bioflavonoid rutin by complexation with transition metals. Biochem Pharmacol 61:677–684
Akita M, Tsutsumi D, Kobayashi M et al (2001) Structural change and catalytic activity of horseradish peroxidase in oxidative polymerization of phenol. Biosci Biotechnol Biochem 65:1581–1588
Akkara JA, Kaplan DL, Samuelson et al (1992) Method for synthesizing an enzyme-catalyzed polymerized monolayer. vol 5.143.828. Lowell, Massachusetts: The United States of America as represented by the secretary of the army
Aktas N (2005) Optimization of biopolymerization rate by response surface methodology (RSM). Enzyme Microb Technol 37:441–447
Aktas N, Kibarer G, Tanyolaç A (2000) Effects of reaction conditions on laccase-catalyzed alpha-naphthol polymerization. J Chem Technol Biotechnol 75:840–846
Aktas N, Tanyolaç A (2003) Reaction conditions for laccase catalyzed polymerization of catechol. Bioresour Technol 87:209–214
Angerer PS, Studer A, Witholt B et al (2005) Oxidative polymerization of a substituted phenol with ion-paired horseradish peroxidase in an organic solvent. Macromol 38:6248–6250
Anthoni J, Humeau C, Maia ER et al (2010) Enzymatic synthesis of oligoesculin: Structure and biological activities characterizations. Eur Food Res Technol 231:571–579
Anthoni J, Lionneton F, Wieruszeski JM et al (2008) Investigation of enzymatic oligomerization of rutin. Rasayan J Chem 1:718–731
Antipov AA, Sukhorukov GB, Leporatti S et al (2002) Polyelectrolyte multilayer capsule permeability control. Colloids Surf A 198–200:535–541
Arnao MB, Acosta M, del Rio JA et al (1990) A kinetic study on the suicide inactivation of peroxidase by hydrogen peroxide. Biochim Biophys Acta, Protein Struct Mol Enzymol 1041:43–47
Ayyagari M, Akkara JA, Kaplan DL (1996) Characterization of phenolic polymers synthesized by enzyme-mediated reactions in bulk solvents and at oil-water interfaces. Mater Sci Eng, C 4:169–173
Ayyagari M, Akkara JA, Kaplan DL (1998) Solvent-enzyme-polymer interactions in the molecular-weight control of poly(m-cresol) synthesis in nonaqueous media. In: Gross RA, Kaplan DL, Swift G (ed) Enzymes in polymer synthesis. ACS symposium series 684, Washington
Ayyagari MS, Marx KA, Tripathy SK et al (1995) Controlled free-radical polymerization of phenol derivatives by enzyme-catalyzes reactions in organic solvents. Macromol 28:5192–5197
Baldrian P (2004) Purification and characterization of laccase from the white-rot fungus Daedalea quercina and decolorization of synthetic dyes by the enzyme. Appl Microbiol Biotechnol 63:560–563
Baldrian P (2006) Fungal laccases-occurrence and properties. FEMS Microbiol Rev 30:215–242
Barreca AM, Fabbrini M, Galli C et al (2003) Laccase/mediated oxidation of a lignin model for improved delignification procedures. J Mol Catal B: Enzym 26:105–110
Bilici A, Kaya I, YildIrIm M et al (2010) Enzymatic polymerization of hydroxy-functionalized carbazole monomer. J Mol Catal B: Enzym 64:89–95
Bindhu LV, Abraham ET (2003) Immobilization of horseradish peroxidase on chitosan for use in nonaqueous media. J Appl Polym Sci 88:1456–1464
Bindhu LV, Emilia Abraham T (2003) Preparation and kinetic studies of surfactant-horseradish peroxidase ion paired complex in organic media. Biochem Eng J 15:47–57
Bourbonnais R, Paice MG, Freiermuth B et al (1997) Reactivities of various mediators and laccases with kraft pulp and lignin model compounds. Appl Environ Microbiol 63:4627–4632
Bruno FF, Akkara JA, Samuelson LA et al (1995) Enzymatic mediated synthesis of conjugated polymers at the Langmuir trough air-water interface. Langmuir 11:889–892
Bruno FF, Nagarajan S, Nagarajan R et al (2005) Biocatalytic synthesis of water-soluble oligo(catechins). J Macromol Sci Pure Appl Chem 42:1547–1554
Burton SG (2003) Laccases and phenol oxidase in organic synthesis—A review. Curr Org Chem 7:1317–1331
Cabana H, Jiwan J-LH, Rozenberg R et al (2007) Elimination of endocrine disrupting chemicals nonylphenol and bisphenol A and personal care product ingredient triclosan using enzyme preparation from the white rot fungus Coriolopsis polyzona. Chemosphere 67:770–778
Canfora L, Iamarino G, Rao MA et al (2008) Oxidative Transformation of Natural and Synthetic Phenolic Mixtures by Trametes versicolor Laccase. J Agric Food Chem 56:1398–1407
Carrea G (1984) Biocatalysis in water-organic solvent two-phase systems. Trends Biotechnol 2:102–106
Chelikani R, Kim YH, Yoon DY et al (2009) Enzymatic polymerization of natural anacardic acid and antibiofouling effects of polyanacardic acid coatings. Appl Biochem Biotechnol 157:263–277
Claus H (2004) Laccases: Structure, reactions, distribution. Micron 35:93–96
Dec J, Bollag JM (1990) Detoxification of substituted phenols by oxidoreductive enzymes through polymerization reactions. Arch Environ Contam Toxicol 19:543–550
Desentis-Mendoza RM, Hernandez-Sanchez H, Moreno A et al (2006) Enzymatic polymerization of phenolic compounds using laccase and tyrosinase from Ustilago maydis. Biomacromolecules 7:1845–1854
Dordick JS, Marletta MA, Klibanov AM (1987) Polymerization of phenols catalyzed by peroxidase in nonaqueous media. Biotechnol Bioeng 30:31–36
Dubey S, Singh D, Misra RA (1998) Enzymatic synthesis and various properties of poly(catechol). Enzyme Microb Technol 23:432–437
Duran N, Rosa MA, D’Annibale A et al (2002) Applications of laccases and tyrosinases (phenoloxidases) immobilized on different supports: a review. Enzyme Microb Technol 31:907–931
Durante D, Casadio R, Martelli L et al (2004) Isothermal and non-isothermal bioreactors in the detoxification of waste waters polluted by aromatic compounds by means of immobilised laccase from Rhus vernicifera. J Mol Catal B: Enzym 27:191–206
Eker B, Zagorevski D, Zhu G et al (2009) Enzymatic polymerization of phenols in room-temperature ionic liquids. J Mol Catal B: Enzym 59:177–184
Faure A, Bouillant ML, Jacoud C et al (1995) Phenolic derivatives related to lignin metabolism as substrates for azospirillum laccase activity. Phytochemistry 42:357–359
Fenoll LG, Garcia-Ruiz PA, Varon R et al (2003) Kinetic Study of the Oxidation of Quercetin by Mushroom Tyrosinase. J Agric Food Chem 51:7781–7787
Friedman M, Jurgens HS (2000) Effect of pH on the Stability of Plant Phenolic Compounds. J Agric Food Chem 48:2101–2110
Fulcrand H, Doco T, Es-Safi N-E et al (1996) Study of the acetaldehyde induced polymerisation of flavan-3-ols by liquid chromatography-ion spray mass spectrometry. J Chromatogr A 752:85–91
Ghan R, Shutava T, Patel A, et al (2003) Layer-by-layer engineered microreactors for bio-polymerization of 4-(2-aminoethyl) phenol hydrochloride. In: Materials research society symposium––proceedings 782:241
Ghan R, Shutava T, Patel A et al (2004) Enzyme-catalyzed polymerization of phenols within polyelectrolyte microcapsules. Macromol 37:4519–4524
Gianfreda L, Xu F, Bollag J-M (1999) Laccases: a useful group of oxidoreductive enzymes. Biorem J 3:1–25
Guresir M, Aktas N, Tanyolac A (2005) Influence of reaction conditions on the rate of enzymic polymerization of pyrogallol using laccase. Process Biochem 40:1175–1182
Havsteen BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Ther 96:67–202
Heim KE, Tagliaferro AR, Bobilya DJ (2002) Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 13:572–584
Hinckley G, Mozhaev VV, Budde C et al (2002) Oxidative enzymes possess catalytic activity in systems with ionic liquids. Biotechnol Lett 24:2083–2087
Hudson EP, Eppler RK, Clark DS (2005) Biocatalysis in semi-aqueous and nearly anhydrous conditions. Curr Opin Biotechnol 16:637–643
Ikeda R, Sughihara J, Uyama H et al (1998) Enzymatic oxidative polymerization of 4-hydroxybenzoic acid derivatives to poly(phenylene oxide)s. Polym Int 47:295–301
Ikeda R, Sugihara J, Uyama H et al (1996a) Enzymatic oxidative polymerization of 2,6-dimethylphenol. Macromol 29:8702–8705
Ikeda R, Tsujimoto T, Tanaka H et al (2000) Man-made urushi. Proc Jpn Acad 76:155–160
Ikeda R, Uyama H, Kobayashi S (1996b) Novel synthetic pathway to a poly(phenylene oxide). laccase-catalyzed oxidative polymerization of syringic acid. Macromol 29:3053–3054
Intra A, Nicotra S, Riva S, et al (2005) Significant and unexpected solvent influence on the selectivity of laccase-catalyzed coupling of tetrahydro-2-naphtol derivatives. Adv Synth Catal, 347:973–977
Job D, Dunford HB (1976) Substituent effect on the oxidation of phenols and aromatic amines by horseradish peroxidase compound I. Eur J Biochem 66:607–614
Kamiya N, Inoue M, Goto M et al (2000) Catalytic and structural properties of surfactant-horseradish peroxidase complex in organic media. Biotechnol Progr 16:52–58
Khmelnitsky YL, Gladilin AK, Roubailo VL et al (1992) Reversed micelles of polymeric surfactants in nonpolar organic solvents. A new microheterogeneous medium for enzymatic reactions. Eur J Biochem 206:737–745
Kim S, Silva C, Zille A et al (2009) Characterisation of enzymatically oxidised lignosulfonates and their application on lignocellulosic fabrics. Polym Int 58:863–868
Kim Y-J, Chung JE, Kurisawa M et al (2004a) New Tyrosinase Inhibitors, (+)-Catechin-Aldehyde Polycondensates. Biomacromolecules 5:474–479
Kim Y-J, Nicell, JA (2006a) Impact of reaction conditions on the laccase-catalyzed conversion of bisphenol A. Bioresour Technol 97:1431–1442
Kim Y-J Uyama H, Kobayashi S (2003a) Regioselective synthesis of poly(phenylene) as a complex with poly(ethylene glycol) by template polymerization of Phenol in water. Macromol 36:5058–5060
Kim YH, An ES, Song BK et al (2003b) Polymerization of cardanol using soybean peroxidase and its potential application as anti-biofilm coating material. Biotechnol Lett 25:1521–1524
Kim YJ, Nicell JA (2006b) Impact of reaction conditions on the laccase-catalyzed conversion of bisphenol A. Bioresour Technol 97:1431–1442
Kim YJ, Shibata K, Uyama H et al (2008) Synthesis of ultrahigh molecular weight phenolic polymers by enzymatic polymerization in the presence of amphiphilic triblock copolymer in water. Polymer 49:4791–4795
Kim YJ, Uyama H, Kobayash S (2004b) Enzymatic template polymerization of phenol in the presence of water-soluble polymers in an aqueous medium. Polym J 36:992–998
Ko KEM, Leem Leem YE et al (2001) Purification and characterization of laccase isozymes from the white-rot basidiomycete Ganoderma lucidum. Appl Microbiol Biotechnol 57:98–102
Kobayashi S, Higashimura H (2003) Oxidative polymerization of phenols revisited. Prog Polym Sci 28:1015–1048
Kobayashi S, Kurioka H, Uyama H (1996) Enzymatic synthesis of a soluble polyphenol derivative from 4,4’-biphenyldiol. Macromol Rapid Comm 17:503–508
Kobayashi S, Uyama H, Kimura S (2001) Enzymatic polymerization. Chem Rev 101:3793–3818
Koroleva OV, Yavmetdinov IS, Shleev SV et al (2001) Isolation and study of some properties of laccase from the Basidiomycetes Cerrena maxima. Biochemistry (Moscow) 66:618–622
Krajewska B (2004) Application of chitin- and chitosan-based materials for enzyme immobilizations: a review. Enzyme Microb Technol 35:126–139
Kurioka H, Komatsu I, Uyama H et al (1994) Enzymatic oxidative polymerization of alkylphenols. Macromol Rapid Comm 15:507–510
Kurisawa M, Chung JE, Kim YJ et al (2003a) Amplification of antioxidant activity and xanthine oxidase inhibition of catechin by enzymatic polymerization. Biomacromolecules 4:469–471
Kurisawa M, Chung JE, Uyama H et al (2003b) Enzymatic synthesis and antioxidant properties of poly(rutin). Biomacromolecules 4:1394–1399
Kurisawa M, Chung JE, Uyama H et al (2003c) Enzymatic synthesis and antioxidant properties of poly(rutin). Biomacromolecules 4:1394–1399
Kurisawa M, Chung JE, Uyama H et al (2003d) Laccase-catalyzed synthesis and antioxidant property of poly(catechin). Macromol Biosci 3:758–764
Kurisawa M, Chung JE, Uyama H et al (2003e) Laccase-catalyzed synthesis and antioxidant property of poly(catechin). Macromol Biosci 3:758–764
Kurniawati S, Nicell JA (2008) Characterization of Trametes versicolor laccase for the transformation of aqueous phenol. Bioresour Technol 99:7825–7834
Lalot T, Brigodiot M, Maréchal E (1999) A kinetic approach to acrylamide radical polymerization by horse radish peroxidase-mediated initiation. Polym Int 48:288–292
Laszlo JA, Compton DL (2002) Comparison of peroxidase activities of hemin, cytochrome c and microperoxidase-11 in molecular solvents and imidazolium-based ionic liquids. J Mol Catal B: Enzym 18:109
Lee MY, Srinivasan A, Ku B et al (2003) Multienzyme catalysis in microfluidic biochips. Biotechnol Bioeng 83:20–28
Ma H-L, Kermasha S, Gao J-M et al (2009) Laccase-catalyzed oxidation of phenolic compounds in organic media. J Mol Catal B Enzym 57:89–95
Maalej-Kammoun M, Zouari-Mechichi H, Belbahri L et al (2009) Malachite green decolourization and detoxification by the laccase from a newly isolated strain of Trametes sp. Int Biodeterior Biodegrad 63:600–606
Mai C, Majcherczyk A, Hüttermann A (2000) Chemo-enzymatic synthesis and characterization of graft copolymers from lignin and acrylic compounds. Enzyme Microb Technol 27:167–175
Marjasvaara A, Torvinen M, Kinnunen H et al (2006) Laccase-catalyzed polymerization of two phenolic compounds studied by matrix-assisted laser desorption/ionization time-of-flight and electrospray ionization fourier transform ion cyclotron resonance mass spectrometry with collision-induced dissociation experiments. Biomacromolecules 7:1604–1609
Martinek K, Levashov AV, Khmelnitsky NL et al (1982) Colloidal solution of water in organic solvents: a microheterogeneous medium for enzymatic reactions. Science 218:889–891
Michizoe J, Goto M (2001) S. F. Catalytic activity of lactase hosted in reversed micelles. J Biosci Bioeng 92:67–71
Milstein O, Nicklas B, Hüttermann A (1989) Oxidation of aromatic compounds in organic solvents with laccase from Trametes versicolor. Appl Microbiol Biotechnol 31:70–74
Mita N, Tawaki SI, Uyama H et al (2002) Enzymatic oxidative polymerization of phenol in an aqueous solution in the presence of a catalytic amount of cyclodextrin. Macromol Chem Phys 203:127–130
Mita N, Tawaki SI, Uyama H et al (2003) Laccase-catalyzed oxidative polymerization of phenols. Macromol Biosci 3:253–257
Mita N, Tawaki SI, Uyama H et al (2004) Precise structure control of enzymatically synthesized polyphenols. Bull Chem Soc Jpn 77:1523–1527
Morozova OV, Shumakovich GP, Gorbacheva MA, Shleev SV, Yaropolov AI (2007) “Blue” laccases. Biochemistry (Moscow) 72:1136–1150
Murugesan K, Kim Y-M, Jeon J-R et al (2009) Effect of metal ions on reactive dye decolorization by laccase from Ganoderma lucidum. J Hazard Mater 168:523–529
Mustafa R, Muniglia L, Rovel B et al (2005) Phenolic colorants obtained by enzymatic synthesis using a fungal laccase in a hydro-organic biphasic system. Food Res Int 38:995–1000
Nabid MR, Zamiraei Z, Sedghi R et al (2010) Synthesis and characterization of poly(catechol) catalyzed by porphyrin and enzyme. Polym Bull 64:855–865
Nayak PL (1998) Enzyme-catalyzed polymerization: an opportunity for innovation. Des Monomers Polym 1:259–284
Ncanana S, Baratto L, Roncaglia L et al (2007) Laccase-mediated oxidation of totarol. Adv Synth Catal 349:1507–1513
Nicell JA, Saadi KW, Buchanan ID (1995) Phenol polymerization and precipitation by horseradish peroxidase enzyme and an additive. Bioresour Technol 54:302–310
Nugroho Prasetyo E, Kudanga T, Østergaard L et al (2010) Polymerization of lignosulfonates by the laccase-HBT (1-hydroxybenzotriazole) system improves dispersibility. Bioresour Technol 101:5054–5062
Oguchi T, Tawaki SI, Uyama H et al (2000) Enzymatic synthesis of soluble polyphenol. Bull Chem Soc Jpn 73:1389–1396
Osiadacz J, Al-Adhami AJH, Bajraszewska D et al (1999) On the use of Trametes versicolor laccase for the conversion of 4-methyl-3-hydroxyanthranilic acid to actinocin chromophore. J Biotechnol 72:141–149
Paradkar VM, Dordick JS (1994a) Aqueous-like activity of alpha-chymotrypsin dissolved in nearly anhydrous organic solvents. J Am Chem Soc 116:5009–5010
Paradkar VM, Dordick JS (1994b) Mechanism of extraction of chymotrypsin into isooctane at very low concentrations of aerosol OT in the absence of reversed micelles. Biotechnol Bioeng 43:529–540
Peralta-Zamora P, Pereira CM, Tiburtius ERL et al (2003) Decolorization of reactive dyes by immobilized laccase. Appl Catal B, 42:131
Pilz RP, Hammer EH, Schauer FS et al (2003) Laccase-catalysed synthesis of coupling products of phenolic substrates in different reactors. Appl Microbiol Biotechnol 60:708–712
Poulos TL (1993) Peroxidases. Curr Opin Biotechnol 4:484–489
Premachandran RS, Banerjee S, Wu XK et al (1996) Enzymatic synthesis of fluorescent naphtol-based polymers. Macromol 29:6452–6460
Rao AM, John VT, Gonzales RD et al (1993) Catalytic and interfacial aspects of enzymatic polymer synthesis in reversed micellar systems. Biotechnol Bioeng 41:531–540
Reihmann H, Ritter (2001) Oxidative Copolymerisation of para-functionalized phenols catalyzed by Horseradish peroxidase and Thermocrosslinking via Diels-Alder and (1 + 3) Cycloaddition. Macromol Biosci 1:85–90
Reihmann MH, Ritter H (2000) Enzymatically catalyzed synthesis of photocrosslinkable oligophenols. MacromolChemPhys 201:1593–1597
Rittstieg K, Suurnakki A, Suortti T et al (2002) Investigations on the laccase-catalyzed polymerization of lignin model compounds using size-exclusion HPLC. Enzyme Microb Technol 31:403–410
Riva S (2006) Laccases: blue enzymes for green chemistry. Trends Biotechnol 24:219–226
Rodakiewicz-Nowak J (2000) Phenols oxidizing enzymes in water-restricted media. Top Catal 11–12:419–434
Rogalski J, Jozwik E, Hatakka A et al (1995) Immobilization of laccase from Phlebia radiata on controlled porosity glass. J Mol Catal A Chem 95:99–108
Roubaty JL, Bréant M, Lavergne M et al (1978) Mechanism of the oxidative coupling of phenols: influence of pH upon the electrochemical oxidation of xylenol in methanol. Makromol Chem 179:1151–1157
Samuelson LA, Tripathy SK, Bruno F, et al (2003) Enzymatic polymerization of anilines or phenols around a template. vol US 6.569.651 B1. The United States of America as represented by the secretary of the army, lowell, Massachusetts
Seelbach K, Van Deurzen MPJ, Van Rantwijk F et al (1997) Improvement of the total turnover number and space-time yield for chloroperoxidase catalyzed oxidation. Biotechnol Bioeng 55:283–288
Shingo K, Tashiaki U, Higushi T (1989) Oxidation of methoxylated benzyl alcohols by laccase of Coriolus versicolor in the presence of syringaldehyde. Wood Res 76:10–16
Shleev S, Jarosz-Wilkolazka A, Khalunina A et al (2005) Direct electron transfer reactions of laccases from different origins on carbon electrodes. Bioelectrochem 67:115–124
Shleev S, Reimann CT, Serezhenkov V et al (2006) Autoreduction and aggregation of fungal laccase in solution phase: possible correlation with a resting form of laccase. Biochimie 88:1275–1285
Solomon EIAAJ, Yoon J (2008) O2 reduction to H2O by the multicopper oxidases. Dalton Transactions 3921–3932
Solomon EI, Sundaram UM, Machonkin TE (1996) Multicopper oxidases and oxygenases. Chem Rev 96:2563–2605
Tanaka T, Takahashi M, Hagino H et al (2010) Enzymatic oxidative polymerization of methoxyphenols. Chem Eng Sci 65:569–573
Tavares APM, Rodriguez O, Macedo EA (2008) Ionic liquids as alternative co-solvents for laccase: study of enzyme activity and stability. Biotechnol Bioeng 101:201–207
Tonami H, Uyama H, Kobayashi S et al (2000) Chemoselective oxidative polymerization of m-ethynylphenol by peroxidase catalyst to a new reactive polyphenol. Biomacromolecules 1:149–151
Uyama H, Kurioka H, Kobayashi S (1997) Novel bienzymatic catalysis system for oxidative polymerization of phenols. Polym J 29:190–192
Uyama H, Maruichi N, Tonami H et al (2002) Peroxidase-catalyzed oxidative polymerization of bisphenols. Biomacromolecules 3:187–193
Uzan E, Portet B, Lubrano C et al (2011) Pycnoporus laccase-mediated bioconversion of rutin to oligomers suitable for biotechnology applications. Appl Microbiol Biotechnol 90:97–105
van Acker SABE, de Groot MJ, van den Berg D-J et al (1996) A quantum chemical explanation of the antioxidant activity of flavonoids. Chem Res Toxicol 9:1305–1312
Van De Velde F, Lourenco ND, Bakker M et al (2000) Improved operational stability of peroxidases by coimmobilization with glucose oxidase. Biotechnol Bioeng 69:286–291
van de Velde F, van Rantwijk F, Sheldon RA (2001) Improving the catalytic performance of peroxidases in organic synthesis. Trends Biotechnol 19:73–79
Van Deurzen MPJ, Van Rantwijk F, Sheldon RA (1997) Selective oxidations catalyzed by peroxidases. Tetrahedron 53:13183–13220
Van Rantwijk F, Lau RM, Sheldon RA (2003) Biocatalytic transformations in ionic liquids. Trends Biotechnol 21:131–138
Wagner M, Nicell JA (2002) Impact of dissolved wastewater constituents on peroxidase-catalyzed treatment of phenol. J Chem Technol Biotechnol 77:419–428
Welinder KG (1992) Superfamily of plant, fungal and bacterial peroxidases. Curr Opin Struct Biol 2:388–393
Witayakran S, Ragauskas AJ (2009) Synthetic applications of laccase in green chemistry. Adv Synth Catal 351:1187–1209
Xia Z, Yoshida T, Funaoka M (2003) Enzymatic synthesis of polyphenols from highly phenolic lignin-based polymers (lignophenols). Biotechnol Lett 25:9–12
Xu F (1996) Oxidation of phenols, anilines, and benzenethiols by fungal laccases: correlation between activity and redox potentials as well as halide inhibition. Biochemistry 35:7608–7614
Xu F (1997) Effects of redox potential and hydroxide inhibition on the pH activity profile of fungal laccases. J Biol Chem 272:924–928
Xu F, Berka RM, Wahleithner JA et al (1998) Site-directed mutations in fungal laccase: effect on redox potential, activity and pH profile. Biochem J 334(Pt 1):63–70
Yang Z, Pan W (2005) Ionic liquids: green solvents for nonaqueous biocatalysis. Enzyme Microb Technol 37:19–28
Yoshida T, Lu R, Han S et al (2009) Laccase-catalyzed polymerization of lignocatechol and affinity on proteins of resulting polymers. J Polym Sci, Part A: Polym Chem 47:824–832
Yu JH, Klibanov AM (2006) Co-lyophilization with d-proline greatly enhances peroxidase’s stereoselectivity in a non-aqueous medium. Biotechnol Lett 28:555
Yun Peng HL, Zhang Xingyuan, Li Yuesheng, Liu Shiyong (2009) CNT templated regioselective enzymatic polymerization of phenol in water and modification of surface of MWNT thereby. J Polym Sci, Part A: Polym Chem 47:1627–1635
Zaragoza-Gasca P, Gimeno M, Hernández JM et al (2011) Novel photoconductive polyfluorophenol synthesized by an enzyme. J Mol Catal B Enzym 72:25–27
Zhu QY, Holt RR, Lazarus SA et al (2002) Stability of the Flavan-3-ols epicatechin and catechin and related dimeric procyanidins derived from cocoa. J Agric Food Chem 50:1700–1705
Acknowledgments
The authors would like to acknowledge Julie Anthoni and Ghada Ben Rhouma for their contribution in the realization of this book. Also, we would like to acknowledge Rasayan Journal for their permission to reuse figures.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2012 The Author(s)
About this chapter
Cite this chapter
Ghoul, M., Chebil, L. (2012). Enzymatic Polymerization of Phenolic Compounds by Oxidoreductases. In: Enzymatic polymerization of phenolic compounds by oxidoreductases. SpringerBriefs in Molecular Science(). Springer, Dordrecht. https://doi.org/10.1007/978-94-007-3919-2_1
Download citation
DOI: https://doi.org/10.1007/978-94-007-3919-2_1
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-007-3918-5
Online ISBN: 978-94-007-3919-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)