ArylAlcohol Oxidase, a Rare Auxiliary Enzyme: It’s Role in Lignin Degradation and Its Potential Applications

Authors

  • Antharikha Dutta Department of Chemistry, North Eastern Regional Institute of Science and Technology, Itanagar 791109, India
  • Neki Borang Department of Chemistry, North Eastern Regional Institute of Science and Technology, Itanagar 791109, India
  • Meera Yadav Department of Chemistry, North Eastern Regional Institute of Science and Technology, Itanagar 791109, India

DOI:

https://doi.org/10.48048/tis.2025.9715

Keywords:

Aryl alcohol oxidase, Flavin adenine dinucleotide, Glucose methanol choline, Oxidoreductase, Basidiomycete, Ascomycete, White-rot fungi, Brown-rot fungi

Abstract

The 2nd most abundant biopolymer after cellulose is lignin, which has a very complex structure and its biological degradation required an enzymatic consortium of different lignin degrading enzymes like Lignin peroxidase (EC 1.11.1.14), Manganese peroxidase (EC 1.11.1.13), Versatile peroxidase (EC 1.11.1.16), Laccase (EC 1.10.3.2) etc. This enzyme required hydrogen peroxide for its action which is supplied by auxillary enzyme like aryl alcohol oxidase. Aryl alcohol oxidase belongs to glucose methanol choline (GMC) superfamily and has FAD as the cofactor. The structural aspects of the enzyme are compared using PeAAO and MtAAOas model. The mechanistic and substrate chemistry of aryl alcohol oxidase as alcohol or aldehyde oxidase is discussed in detail. The enhance activity as alcohol oxidase of ‘aryl alcohol oxidase’ using electron donating substrate, which is opposite when its aldehyde oxidase activity is considered. The application of the enzyme as an efficient dye degrading enzyme for wastewater treatment biologically, or in paper-pulp bio-bleaching, or drug design make it a hot topic of research for various industrial purpose and commercialization. Other mentionable application of the enzyme, is in the production of flavours and fragrances like vanillin, benzaldehyde, trans-2-hexanal, trans-2-cis-6-nonadienal, piperonal, perillaldehydeetc. The role of the enzyme in the synthesis of bio-based precursors like HMF, FFCA or FDCA is also discussed.

HIGHLIGHTS

  • Aryl alcohol oxidase (E C 1.1.3.7) plays a significant role in lignin degradation by supplying hydrogen peroxide to lignin degrading enzymes.
  • It acts upon both alcoholic and aldehydic substrates and convert them to corresponding aldehyde or acids.
  • It is secreted by white-rot and brown-rot fungi, mostly and it is a member of GMC oxidoreductase superfamily.
  • In the enzymatic consortium for lignin degradation biologically, aryl alcohol oxidase plays the role as a versatile auxiliary enzyme.
  • The enzyme seems, to have very wide scale industrial applications in flavors or fragrance industry or drug design or synthesis of bio-based precursor like HMF, FDCA, and FFCA etc.

GRAPHICAL ABSTRACT

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Author Biography

Antharikha Dutta, Department of Chemistry, North Eastern Regional Institute of Science and Technology, Itanagar 791109, India

Research Scholar

Department of Chemistry

North Eastern Regional Institute of Science and Technology

Nirjuli, Itanagar-791109

A.P India

References

E Romero, JRG Castellanos, G Gadda, MW Fraaije and A Mattevi. Same substrate, many reactions: Oxygen activation in flavoenzymes. Chemical Reviews 2018; 118(4), 1742-1769.

TDHBugg, M Ahmad, EM Hardiman and R Rahmanpour. Pathways for degradation of lignin in bacteria and fungi. Natural Product Reports 2011; 28(12), 1883-1896.

T Higuchi. Biodegradation of lignin: Biochemistry and potential applications. In: HMislin and R Bachofen (Eds.). New trends in research and utilization of solar energy through biological systems. BirkhӓuserBasel, Basel, Switzerland, 1982, p. 87-94.

W Horwath. Carbon cycling and formation of soil organic matter. In: Soilmicrobiology, ecology and biochemistry. Academic Press, Cambridge, 2007, p. 303-339.

ÁT Martínez, J Rencoret, G Marques, A Gutiérrez, D Ibarra, J Jiménez-Barbero and JCD Río. Monolignol acylation and lignin structure in some nonwoody plants: A 2D NMR study. Phytochemistry 2008; 69(16), 2831-2843.

K Isobe and Y Kawakami. Preparation of convection interaction media isobutyl discmonolithic column and its application to purification of secondary alcohol dehydrogenase and alcohol oxidase. Journal of Chromatography A 2007; 1144(1), 85-89.

J Zakzeski, PC Bruijnincx, AL Jongerius and BM Weckhuysen. The catalytic valorization of lignin for the production of renewable chemicals. Chemical Reviews 2010; 110(6), 3552-3599.

DP Tamboli, AATelke, VV Dawkar, SB Jadhav and SP Govindwar. Purification and characterization of bacterial aryl alcohol oxidase from Sphingobacteriumsp. ATM and its uses in textile dye decolorization. Biotechnology and Bioprocess Engineering 2011; 16, 661-668.

A Hernández-Ortega, K Borrelli, P Ferreira, M Medina, AT Martinez and VGuallar. Substrate diffusion and oxidation in GMC oxidoreductases: An experimental andcomputational study on fungal aryl-alcohol oxidase. Biochemical Journal 2011; 436(2), 341-350.

F Fan, MW Germann and G Gadda. Mechanistic studies of choline oxidase with betaine aldehyde and its isosteric analogue 3,3-dimethylbutyraldehyde. Biochemistry 2006; 45(6), 1979-1986.

IS Fernández, FJ Ruiz-Duenas, E Santillana, P Ferreira, MJ Martínez, ÁT Martínez and ARomero. Novel structural features in the GMC family of oxidoreductases revealed by the crystal structure of fungal aryl-alcohol oxidase. Acta Crystallographica Section D: Biological Crystallography 2009; 65(11), 1196-1205.

JC Sigoillot, S Camarero, T Vidal, E Record and M Asther. Laccase-catalyzed oxidation of aryl alcohols in lignin degradation. Applied Microbiology and Biotechnology 2004; 64(6), 793-799.

A Lappe, N Jankowski, A Albrecht and K Koschorreck. Characterization of a thermotolerant aryl-alcohol oxidase from Moesziomyces antarcticus oxidizing 5-hydroxymethyl-2-furancarboxylic acid. Applied Microbiology and Biotechnology 2021; 105, 8313-8327.

A Serrano, E Calviño, J Carro, MI Sánchez-Ruiz, FJ Cañada and AT Martínez. Complete oxidation of hydroxymethylfurfural to furandicarboxylic acid by aryl-alcohol oxidase. Biotechnology for Biofuels 2019; 12, 1-12.

J MacLachlan, ATWotherspoon, RO Ansell and CJ Brooks. Cholesterol oxidase: Sources, physical properties and analytical applications. The Journal ofSteroid Biochemistry and Molecular Biology 2000; 72(5), 169-195.

S Varjani, PRakholiya, HY Ng, S You and JA Teixeira.Microbial degradation of dyes: An overview. Bioresource Technology 2020; 314, 123728.

VC Farmer, ME Henderson and JD Russell. Aromatic-alcohol-oxidase activity in the growth medium of Polystictus versicolor. Biochemical Journal 1960; 74(2), 257.

R Bourbonnais and MG Paice. Veratryl alcohol oxidases from the lignin-degradingbasidiomycete Pleurotus sajor-caju. Biochemical Journal 1988; 255(2), 445-450.

A Hernández‐Ortega, P Ferreira, P Merino, M Medina, V Guallar and AT Martínez. Stereoselective hydride transfer by aryl‐alcohol oxidase, a member of the GMC superfamily. ChemBioChem 2012; 13(3), 427-435.

AK Kumar and P Goswami. Purification and properties of a novel broad substrate specific alcohol oxidase from Aspergillus terreus MTCC 6324.Biochimica et Biophysica Acta-Proteins and Proteomics 2008; 1784(11), 1552-1559.

V Regalado, F Perestelo, A Rodriguez, ACarnicero, FJ Sosa, GDL Fuente and MAFalcon. Activated oxygen species and two extracellular enzymes: Laccase andaryl-alcohol oxidase, novel for the lignin-degrading fungus Fusarium proliferatum. Applied Microbiology and Biotechnology 1999; 51, 388-390.

Y Asada, A Watanabe, Y Ohtsuand M Kuwahara. Purification and characterization of an aryl-alcohol oxidase from the lignin-degrading basidiomycete Phanerochaetechrysosporium. Bioscience, Biotechnology, and Biochemistry 1995; 59(7), 1339-1341.

L Sützl, G Foley, EM Gillam, M Bodén and D Haltrich. The GMC superfamily of oxidoreductases revisited: Analysis and evolution of fungal GMCoxidoreductases.Biotechnology for Biofuels2019; 12, 118.

I Galperin, A Javeed, H Luig, GLochnit and MRühl.An aryl-alcohol oxidase of Pleurotus sapidus: Heterologous expression, characterization, and application in a 2-enzymesystem. Applied Microbiology and Biotechnology 2016; 100(18), 8021-8030.

FS Chakar and AJ Ragauskas. Review of current and future softwood kraft lignin process chemistry. Industrial Crops and Products2004;20(2), 131-141.

M Couturier, Y Mathieu, A Li, D Navarro, EDrula, M Haon, S Grisel, R Ludwig and JG Berrin. Characterization of a new aryl-alcohol oxidase secreted by the phytopathogenic fungus Ustilagomaydis. Applied Microbiology and Biotechnology 2016; 100(2), 697-706.

TK Lundell, MR Mäkelä, RPD Vries and KS Hildén. Genomics, lifestyles and future prospects of wood-decay and litter-decomposing basidiomycota. Advances in Botanical Research 2014; 70, 329-370.

M Kiess, HJ Hecht and HM Kalisz. Glucose oxidase from Penicilliumamagasakiense: Primary structure and comparison with other glucose‐methanol‐choline (GMC) oxidoreductases. European Journal of Biochemistry 1998; 252(1), 90-99.

M Chakraborty, M Goel, SRChinnadayyala, UR Dahiya, SS Ghosh and P Goswami. Molecular characterization and expression of a novel alcohol oxidase from Aspergillusterreus MTCC6324. PLoS One 2014; 9(4), e95368.

TC Joshni and K Subramaniam. Enzymatic degradation of azo dyes - A review. International Journal of Environmental Sciences 2011; 1(6), 1250-1260.

FA Riyadi, AA Tahir, N Yusof, NSA Sabri, MJMM Noor, FNM Akhir and H Hara. Enzymatic and genetic characterization of lignin depolymerization by Streptomyces sp. S6 isolated from a tropical environment. Scientific Reports 2020; 10(1), 7813.

P Cinca-Fernando, C Ascaso-Alegre, E Sevilla, M Martinez-Julvez, J Mangas-Sanchez and P Ferreira. Discovery, characterization and synthetic potential of two novel bacterial alcohol oxidases. bioRxiv 2024.

V Mann, A Large, S Khan, Z Malik and MJ Connock.Aromatic alcohol oxidase: A new membrane‐bound H2O2‐generating enzyme in alimentary tissues of the slug Arionater. Journal of Experimental Zoology 1989; 251(3), 265-274.

K Francis and G Gadda. On the use of noncompetitive kinetic isotope effects to investigate flavoenzyme mechanism. Methods in Enzymology 2019; 620, 115-143.

E Romero, P Ferreira, ÁT Martínez and MJ Martínez. New oxidase from Bjerkanderaarthroconidial anamorph that oxidizes both phenolic and nonphenolic benzyl alcohols. Biochimica et Biophysica Acta-Proteins and Proteomics 2009; 1794(4), 689-697.

AT Martínez, M Speranza, FJ Ruiz-Dueñas, P Ferreira, S Camarero, F Guillén and JCDR Andrade. Biodegradation of lignocellulosics: Microbial, chemical, and enzymatic aspects of the fungal attack of lignin. International Microbiology 2005; 8(3), 195-204.

WP Dijkman, GD Gonzalo, AMattevi and MWFraaije.Flavoprotein oxidases: Classification and applications. Applied Microbiology and Biotechnology 2013; 97, 5177-5188.

MW Fraaije, RHVD Heuvel, AMattevi and WJHV Berkel. Covalent flavinylation enhances the oxidative power of vanillyl-alcohol oxidase. Journal of Molecular Catalysis B: Enzymatic 2003; 21(1-2), 43-46.

FJ Ruiz‐Dueñas and ÁT Martínez. Microbial degradation of lignin: How a bulky recalcitrant polymer is efficiently recycled in nature and how we can take advantage of this. Microbial Biotechnology 2009; 2(2), 164-177.

J Carro, P Amengual-Rigo, F Sancho, M Medina, V Guallar, P Ferreira andATMartínez. Multiple implications of an active site phenylalanine in the catalysis of aryl-alcohol oxidase. Scientific Reports 2018; 8(1), 8121.

J Carro, E Fernández-Fueyo, C Fernández-Alonso, J Cañada, R Ullrich, M Hofrichter, M Alcalde, P Ferreira andAT Martínez. Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural. Biotechnology for Biofuels 2028;11, 86.

P Ferreira, M Medina, F Guillén, MJ Martínez, WJV Berkel and ÁT Martínez. Spectral and catalytic properties of aryl-alcohol oxidase, a fungal flavoenzyme acting on polyunsaturated alcohols. Biochemical Journal 2005; 389(3), 731-738.

Y Tamaru, K Umezawa and M Yoshida. Characterization of an aryl-alcohol oxidase from the plant saprophytic basidiomycete Coprinopsis cinerea with broad substrate specificityagainst aromatic alcohols. Biotechnology Letters 2018; 40, 1077-1086.

A Hernández-Ortega, F Lucas, P Ferreira, M Medina, VGuallar and AT Martínez.Role of active site histidines in the two half-reactions of the aryl-alcohol oxidasecatalytic cycle. Biochemistry 2012; 51(33), 6595-6608.

A Hernández-Ortega, P Ferreira and ATMartínez.Fungal aryl-alcohol oxidase: A peroxide-producing flavoenzyme involved in lignin degradation. Applied Microbiology and Biotechnology 2012; 93(4), 1395-1410.

A Hernández‐Ortega, P Ferreira, P Merino, M Medina, VGuallar and AT Martínez.Stereoselective hydride transfer by aryl‐alcohol oxidase, a member of the GMCsuperfamily. ChemBioChem 2012; 13(3), 427-435.

J Sucharitakul, TWongnate and P Chaiyen. Hydrogen peroxide elimination fromC4a-hydroperoxyflavin in a flavoprotein oxidase occurs through a single proton transfer from flavin N5 to a peroxide leaving group. Journal of Biological Chemistry 2011; 286(19), 16900-16909.

P Ferreira, A Hernandez-Ortega, BHerguedas, ÁT Martínez and M Medina. Aryl-alcohol oxidase involved in lignin degradation: A mechanistic study based on steady and presteady state kinetics and primary and solvent isotope effects with two alcoholsubstrates. Journal of Biological Chemistry 2009; 284(37), 24840-24847.

P Ferreira, A Hernández-Ortega, BHerguedas, JRencoret, A Gutiérrez, MJ Martínez, J Jiménez-Barbero, MMedina and AT Martínez. Kinetic and chemical characterization of aldehyde oxidation byfungal aryl-alcohol oxidase. Biochemical Journal 2010; 425(3), 585-593.

N Jankowski, KKoschorreck and VBUrlacher.High-level expression of aryl-alcohol oxidase 2 from Pleurotus eryngiiinPichia pastoris for production of fragrances andbioactive precursors. Applied Microbiology and Biotechnology 2020; 104(21), 9205-9218.

A Serrano, F Sancho, J Viña-González, J Carro, M Alcalde, VGuallar and AT Martínez. Switching the substrate preference of fungal aryl-alcohol oxidase: Towards stereoselective oxidation of secondary benzyl alcohols. Catalysis Science and Technology 2019; 9(3), 833-841.

J Galbán, I Sanz-Vicente, J Navarro and SD Marcos. The intrinsic fluorescence of FAD and its application in analytical chemistry: A review. Methods and Applications in Fluorescence 2016; 4(4),42005.

E Varela, BBöckle, A Romero, ATMartı́nez and MJ Martı́nez. Biochemical characterization, cDNA cloning and protein crystallization of aryl-alcohol oxidase fromPleurotus pulmonarius. Biochimica et Biophysica Acta - Protein Structure and Molecular Enzymology 2000; 1476(1), 129-138.

P Schieberle, S Ofner and W Grosch.Evaluation of potent odorants in cucumbers (Cucumis sativus) and muskmelons (Cucumis melo) by aroma extract dilutionanalysis. Journal of Food Science 1990; 55(1), 193-195.

J Viña-Gonzalez, D Gonzalez-Perez, P Ferreira, AT Martinez and M Alcalde. Focused directed evolution of aryl-alcohol oxidase in Saccharomyces cerevisiae by usingchimeric signal peptides. Applied and Environmental Microbiology 2015; 81(18), 6451-6462.

M Goetghebeur, M Nicolas, S Brun and P Galzy.Purification and properties of benzyl alcohol oxidase from Botrytis cinerea. Bioscience, Biotechnology, and Biochemistry 1992; 56(2), 298-303.

F Guillén and CS Evans.Anisaldehyde and veratraldehyde acting as redox cycling agents for H2O2 production by Pleurotus eryngii. Applied and Environmental Microbiology 1994; 60(8), 2811-2817.

S Camarero, MJ Martínez and AT Martínez. Understanding lignin biodegradationfor the improved utilization of plant biomass in modern biorefineries. Biofuels, Bioproducts and Biorefining 2014; 8(5), 615-625.

WT Beeson, CM Phillips, JHD Cate and MA Marletta. Oxidative cleavage of cellulose by fungal copper-dependent polysaccharide monooxygenases. Journal of the American Chemical Society 2012; 134(2), 890-892.

FW Janssen, RM Kerwin and HW Ruelius. Alcohol oxidase, a novel enzyme from a basidiomycete. Biochemical and Biophysical Research Communications 1965; 20(5), 630-634.

G Sannia, P Limongi, E Cocca, F Buonocore, G Nitti and P Giardina. Purification and characterization of a veratryl alcohol oxidase enzyme from the lignin degrading basidiomycete Pleurotus ostreatus. Biochimica et Biophysica Acta - General Subjects 1991; 1073(1), 114-119

SJ Kim, N Suzuki, Y Uematsu and M Shoda. Characterization of aryl alcohol oxidase produced by dye-decolorizing fungus, Geotrichumcandidum Decl. Journal of Bioscience and Bioengineering 2001; 91(2), 166-172.

T Shimokawa, M Hirai, M Shoda and Y Sugano. Efficient dye decolorization and production of dye decolorizing enzymes by the basidiomycete Thanatephoruscucumeris Dec1 in a liquid and solid hybrid culture. Journal of Bioscience and Bioengineering 2008; 106(5), 481-487.

P Bajpai, A Anand and PK Bajpai.Bleaching with lignin-oxidizing enzymes. Biotechnology Annual Review 2006; 12, 349-378.

C Sigoillot, S Camarero, T Vidal, E Record, M Asther, M Pérez-Boada and ÁT Martínez. Comparison of different fungal enzymes for bleaching high-quality paper pulps. Journal of Biotechnology 2005; 115(4), 333-343.

VB Urlacher and KKoschorreck. Pecularities and applications of aryl-alcoholoxidases from fungi. Applied Microbiology and Biotechnology 2021; 105, 4111-4126.

MMCHV Schie, TPD Almeida, G Laudadio, FTieves, E Fernández-Fueyo, T Noël, IWCE Arends and F Hollmann. Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor. Beilstein Journal of Organic Chemistry 2018; 14(1), 697-703.

S Sarkar, A Banerjee, U Halder, R Biswas and R Bandopadhyay. Degradation of synthetic azo dyes of textile industry: A sustainable approach using microbial enzymes. Water Conservation Science and Engineering 2017; 2, 121-131.

JA Pino and J Mesa. Contribution of volatile compounds to mango (Mangiferaindica L.) aroma. Flavour and Fragrance Journal 2006; 21(2), 207-213.

N Jankowski, K Koschorreck and VB Urlacher. Aryl‐alcohol‐oxidase‐mediated synthesis of piperonal and other valuable aldehydes. Advanced Synthesis and Catalysis 2022; 364(14), 2364-2372.

N Jankowski, VB Urlacher and K Koschorreck. Two adjacent C-terminal mutations enable expression of aryl-alcohol oxidase from Pleurotus eryngiiinPichia pastoris. Applied Microbiology and Biotechnology 2021; 105, 7743-7755.

A Karich, SB Kleeberg, R Ullrich and M Hofrichter. Enzymatic preparation of 2,5-furandicarboxylic acid (FDCA) - A substitute of terephthalic acid - by the joined action of three fungal enzymes. Microorganisms 2018; 6(1), 5.

J Viña-Gonzalez, AT Martinez, VGuallar and M Alcalde. Sequential oxidation of5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid by an evolved aryl-alcohol oxidase. Biochimica et Biophysica Acta -Proteins and Proteomics 2020; 1868(1), 140293.

AM Abdel-Hamid, JO Solbiati and IKO Cann. Insights into lignin degradation and itspotential industrial applications. Advances in Applied Microbiology 2013;82,1-28.

P Azadi, OR Inderwildi, R Farnood and DA King. Liquid fuels, hydrogen and chemicals from lignin: A critical review. Renewable and Sustainable Energy Reviews 2013; 21, 506-523.

JM Barrasa, A Gutiérrez, VEscaso, F Guillén, MJ Martínez and AT Martínez. Electron and fluorescence microscopy of extracellular glucan and aryl-alcohol oxidase during wheat-straw degradation by Pleurotus eryngii. Applied and Environmental Microbiology 1998; 64(1), 325-332.

M Bellardita, V Loddo, G Palmisano, IPibiri, L Palmisano and V Augugliaro. Photocatalytic green synthesis of piperonal in aqueous TiO2 suspension. Applied Catalysis B: Environmental 2014; 144, 607-613.

M Bey, S Zhou, L Poidevin, B Henrissat, PM Coutinho, JG Berrin and JC Sigoillot. Cello-oligosaccharide oxidation reveals differences between two lytic polysaccharide monooxygenases (family GH61) from Podospora anserina. Applied and Environmental Microbiology 2013; 79(2), 488-496.

M Brückmann, A Termonia, JM Pasteels and T Hartmann. Characterization of anextracellular salicyl alcohol oxidase from larval defensive secretions of Chrysomela populi andPhratoravitellinae (Chrysomelina). Insect Biochemistry and Molecular Biology 2002; 32(11), 1517-1523.

W Cao, B Mahadevan, DL Crawford and RL Crawford. Characterization of an extracellular azo dye-oxidizing peroxidase from Flavobacterium sp. ATCC 39723.Enzyme and Microbial Technology 1993; 15(10), 810-817

J Carro, P Ferreira, AT Martínez and G Gadda. Stepwise hydrogen atom and protontransfers in dioxygen reduction by aryl-alcohol oxidase. Biochemistry 2028; 57(11), 1790-1797.

J Carro, P Ferreira, L Rodríguez, A Prieto, A Serrano, BBalcells, A Ardá, J Jiménez-Barbero, A Gutiérrez, RUllrich, M Hofrichter and AT Martínez. 5‐hydroxymethylfurfural conversion by fungal aryl‐alcohol oxidase and unspecificperoxygenase. The FEBS Journal 2015; 282(16), 3218-3229.

J Carro, M Martínez-Júlvez, M Medina, AT Martínez and P Ferreira. Proteindynamics promote hydride tunnelling in substrate oxidation by aryl-alcohol oxidase. Physical Chemistry Chemical Physics 2017; 19(42), 28666-28675.

DR Cavener. GMC oxidoreductases: A newly defined family of homologous proteins with diverse catalytic activities. Journal of Molecular Biology 1992; 223(3), 811-814.

P Chaiyen, MWFraaije and A Mattevi. The enigmatic reaction of flavins with oxygen. Trends in Biochemical Sciences 2012; 37(9), 373-380.

G Daniel, J Volc, L Filonova, O Plíhal, E Kubátová and P Halada. Characteristicsof Gloeophyllumtrabeum alcohol oxidase, an extracellular source of H2O2 in brown rot decayof wood. Applied and Environmental Microbiology 2007; 73(19), 6241-6253.

TPD Almeida, MMCHV Schie, A Ma, FTieves, SHH Younes, E Fernández‐Fueyo, IWCE Arends, JARiul and F Hollmann. Efficient aerobic oxidation of trans‐2‐hexen‐1‐ol using the aryl alcohol oxidase from Pleurotus eryngii. Advanced Synthesis and Catalysis 2019; 361(11), 2668-2672.

GD Gonzalo, DI Colpa, MH Habib and MWFraaije. Bacterial enzymes involved in lignin degradation. Journal of Biotechnology 2016; 236, 110-119.

EDJong, FPDVries, JA Field, RPVDZwan and JAD Bont. Isolation and screening of basidiomycetes with high peroxidative activity. Mycological Research 1992; 96(12), 1098-1104.

JDOC Brum, DCF Neto, JSFD Almeida, JA Lima, K Kuca, TCC França and JD Figueroa-Villar. Synthesis of new quinoline-piperonal hybrids as potentialdrugs against Alzheimer’s disease. International Journal of Molecular Sciences 2019; 20(16), 3944.

DD Gioia, FLuziatelli, A Negroni, AG Ficca, F Fava and M Ruzzi. Metabolic engineering of Pseudomonas fluorescens for the production of vanillin from ferulic acid. Journal of Biotechnology 2011; 156(4), 309-316.

FM Dickinson and C Wadforth.Purification and some properties of alcohol oxidasefrom alkane-grown Candida tropicalis. Biochemical Journal 1992; 282(2), 325-331.

WP Dijkman and MW Fraaije.Discovery and characterization of a 5-hydroxymethylfurfural oxidase from Methylovorus sp. strain MP688. Applied and Environmental Microbiology 2014; 80(3), 1082-1090.

RD Draper and LL Ingraham.A potentiometric study of the flavin semiquinone equilibrium. Archives of Biochemistry and Biophysics 1968; 125(3), 802-808.

AM Edwards. Structure and general properties of flavins. Methods in Molecular Biology 2014; 1146, 3-13.

I Eichlerová, L Homolka and F Nerud.Ability of industrial dyes decolorization and ligninolytic enzymes production by different Pleurotus species with special attention on Pleurotus calyptratus, strain CCBAS 461. Process Biochemistry 2006; 41(4), 941-946.

ME Jazi, G Narayanan, FAghabozorgi, BFarajidizaji, A Aghaei, MA Kamyabi and TE Mlsna. Structure, chemistry and physicochemistry of lignin for material functionalization. SN Applied Sciences 2019; 1, 1094.

P Ferreira, J Carro, B Balcells, AT Martínez and A Serrano. Expanding the physiological role of aryl-alcohol flavooxidases as quinone reductases. Applied and Environmental Microbiology 2023; 89(5), e0184422.

P Ferreira, A Hernández‐Ortega, F Lucas, J Carro, B Herguedas, KW Borrelli and M Medina. Aromatic stacking interactions govern catalysis in aryl‐alcohol oxidase. The FEBS Journal 2015; 282(16), 3091-3106.

P Ferreira, FJ Ruiz‐Dueñas, MJ Martínez, WJV Berkel and ÁT Martínez. Site‐directed mutagenesis of selected residues at the active site of aryl‐alcohol oxidase, an H2O2‐producing ligninolytic enzyme. The FEBS Journal 2006; 273(21), 4878-4888.

D Floudas, M Binder, R Riley, K Barry, RA Blanchette, B Henrissat, AT Martínez, ROtillar, JW Spatafora, JS Yadav, AAerts, I Benoit, A Boyd, A Carlson, A Copeland, PM Coutinho, RPD Vries, P Ferreira, KFindley, B Foster and DS Hibbett. The paleozoic origin of enzymatic lignin decompositionreconstructed from 31 fungal genomes. Science 2012; 336(6089), 1715-1719.

MW Fraaije and A Mattevi.Flavoenzymes: Diverse catalysts with recurrentfeatures. Trends in Biochemical Sciences 2000; 25(3), 126-132.

MW Fraaije, RHVD Heuvel, WJV Berkel and A Mattevi. Covalent flavinylation is essential for efficient redox catalysis in vanillyl-alcohol oxidase. Journal of Biological Chemistry 1999; 274(50), 35514-35520.

MW Fraaije, C Veeger and WJV Berkel. Substrate specificity of flavin‐dependent vanillyl‐alcohol oxidase fromPenicillium simplicissimum: Evidence for the production of 4‐hydroxycinnamyl alcohols from 4‐allylphenols. European Journal of Biochemistry 1995; 234(1), 271-277.

G Gadda. Hydride transfer made easy in the reaction of alcohol oxidation catalyzed by flavin-dependent oxidases. Biochemistry 2008; 47(52), 13745-13753.

J Galbán, I Sanz-Vicente, J Navarro and SD Marcos. The intrinsic fluorescence of FAD and its application in analytical chemistry: A review. Methods and Applications in Fluorescence 2016; 4(4),42005.

P Goswami, SSR Chinnadayyala, M Chakraborty, AK Kumar and A Kakoti. An overview on alcohol oxidases and their potential applications. Applied Microbiology and Biotechnology 2013; 97, 4259-4275.

F Guillén, AT Martínez and MJ Martínez. Substrate specificity and propertiesof the aryl‐alcohol oxidase from the ligninolytic fungus Pleurotus eryngii. European Journal of Biochemistry 1992; 209(2), 603-611.

A Gutierrez, L Caramelo, A Prieto, MJ Martínez and AT Martinez. Anisaldehydeproduction and aryl-alcohol oxidase and dehydrogenase activities in ligninolytic fungi of thegenus Pleurotus. Applied and Environmental Microbiology 1994; 60(6), 1783-1788.

DP Heuts, NS Scrutton, WS McIntire and MWFraaije. What’s in a covalent bond? On the role and formation of covalently bound flavin cofactors.The FEBS Journal2009; 276(13), 3405-3427.

K Isobe, A Kato, J Ogawa, M Kataoka, AIwasaki, J Hasegawa and S Shimizu. Characterization of alcohol oxidase from Aspergillus ochraceus AIU 031. The Journal of General and Applied Microbiology 2007; 53(3), 177-183.

K Isobe, T Takahashi, J Ogawa, M Kataoka and S Shimizu. Production andcharacterization of alcohol oxidase from Penicillium purpurescens AIU 063. Journal of Bioscience and Bioengineering 2009; 107(2), 108-112.

N Jankowski, K Koschorreck and VB Urlacher. Aryl‐alcohol‐oxidase‐mediated synthesis of piperonal and other valuable aldehydes. Advanced Synthesis and Catalysis 2022; 364(14), 2364-2372.

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2025-07-15