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New enzymatic oxidation/oxyfunctionalization technologies for added value bio-based products

Deliverables

Dissemination and use of main project results, including publications and patent licensing

The main project results will be first protected by patents, for subsequent exploitation by partners and/or third parties (Task 7.3), and then published in scientific and technical journals, and/or presented to scientific congresses and other meetings (Task 7.4)

Brochure describing the main aspects of the project, including objectives and consortium

Related to Task 7.4. The first one (DL7.02) will provide a general introduction to the EnzOx2 project including the objectives, consortium composition and main aspects of the work plan.

Set-up of the project web-site including public and private parts

Development of a project web-site including a public part about the EnzOx2 project (objectives, consortium members and main non-confidential results) and some general aspects of the bio-based industry and the use of enzymes as industrial biocatalysts, and a private part (only for partners) for exchanging confidential information.

Brochure describing the main results and their potential impact on different industrial sectors

Related to Task 7.4. The second brochure (DL7.04) will be produced just after the end of the project and will incorporate to the general information provided in the first brochure, the main results obtained in the course of the project, and their potential impact in different European industrial sectors.

Publications

Mapping the Long-Range Electron Transfer Route in Ligninolytic Peroxidases

Author(s): Sandra Acebes, Francisco J. Ruiz-Dueñas, Mario Toubes, Veronica Sáez-Jiménez, Marta Pérez-Boada, M. Fátima Lucas, Angel T. Martínez, Victor Guallar
Published in: The Journal of Physical Chemistry B, 121/16, 2017, Page(s) 3946-3954, ISSN 1520-6106
Publisher: American Chemical Society
DOI: 10.1021/acs.jpcb.7b00835

High-Throughput Screening Assay for Laccase Engineering toward Lignosulfonate Valorization

Author(s): David Rodríguez-Escribano, Felipe de Salas, Isabel Pardo, Susana Camarero
Published in: International Journal of Molecular Sciences, 18/8, 2017, Page(s) 1793, ISSN 1422-0067
Publisher: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/ijms18081793

Oxidoreductases on their way to industrial biotransformations

Author(s): Angel T. Martínez, Francisco J. Ruiz-Dueñas, Susana Camarero, Ana Serrano, Dolores Linde, Henrik Lund, Jesper Vind, Morten Tovborg, Owik M. Herold-Majumdar, Martin Hofrichter, Christiane Liers, René Ullrich, Katrin Scheibner, Giovanni Sannia, Alessandra Piscitelli, Cinzia Pezzella, Mehmet E. Sener, Sibel Kılıç, Willem J.H. van Berkel, Victor Guallar, Maria Fátima Lucas, Ralf Zuhse, Roland L
Published in: Biotechnology Advances, 35/6, 2017, Page(s) 815-831, ISSN 0734-9750
Publisher: Elsevier BV
DOI: 10.1016/j.biotechadv.2017.06.003

Fungal Unspecific Peroxygenases Oxidize the Majority of Organic EPA Priority Pollutants

Author(s): Alexander Karich, René Ullrich, Katrin Scheibner, Martin Hofrichter
Published in: Frontiers in Microbiology, 8, 2017, ISSN 1664-302X
Publisher: Frontiers Media
DOI: 10.3389/fmicb.2017.01463

Fatty Acid Chain Shortening by a Fungal Peroxygenase

Author(s): Andrés Olmedo, José C. del Río, Jan Kiebist, René Ullrich, Martin Hofrichter, Katrin Scheibner, Angel T. Martínez, Ana Gutiérrez
Published in: Chemistry - A European Journal, 23/67, 2017, Page(s) 16985-16989, ISSN 0947-6539
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201704773

Draft Genome Sequence of the Wood-Degrading Ascomycete Kretzschmaria deusta DSM 104547

Author(s): Enrico Büttner, Anna Maria Gebauer, Martin Hofrichter, Christiane Liers, Harald Kellner
Published in: Genome Announcements, 5/43, 2017, Page(s) e01076-17, ISSN 2169-8287
Publisher: American Society for Microbiology
DOI: 10.1128/genomeA.01076-17

Protein dynamics promote hydride tunnelling in substrate oxidation by aryl-alcohol oxidase

Author(s): Juan Carro, Marta Martínez-Júlvez, Milagros Medina, Angel T. Martínez, Patricia Ferreira
Published in: Physical Chemistry Chemical Physics, 19/42, 2017, Page(s) 28666-28675, ISSN 1463-9076
Publisher: Royal Society of Chemistry
DOI: 10.1039/C7CP05904C

Evolved α-factor prepro-leaders for directed laccase evolution in Saccharomyces cerevisiae

Author(s): Ivan Mateljak, Thierry Tron, Miguel Alcalde
Published in: Microbial Biotechnology, 10/6, 2017, Page(s) 1830-1836, ISSN 1751-7915
Publisher: John Wiley & Sons Ltd
DOI: 10.1111/1751-7915.12838

Stepwise Hydrogen Atom and Proton Transfers in Dioxygen Reduction by Aryl-Alcohol Oxidase

Author(s): Juan Carro, Patricia Ferreira, Angel T. Martínez, Giovanni Gadda
Published in: Biochemistry, 57/11, 2018, Page(s) 1790-1797, ISSN 0006-2960
Publisher: American Chemical Society
DOI: 10.1021/acs.biochem.8b00106

Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural

Author(s): Juan Carro, Elena Fernández-Fueyo, Carmen Fernández-Alonso, Javier Cañada, René Ullrich, Martin Hofrichter, Miguel Alcalde, Patricia Ferreira, Angel T. Martínez
Published in: Biotechnology for Biofuels, 11/1, 2018, ISSN 1754-6834
Publisher: BioMed Central
DOI: 10.1186/s13068-018-1091-2

Side chain removal from corticosteroids by unspecific peroxygenase

Author(s): René Ullrich, Marzena Poraj-Kobielska, Steffi Scholze, Claire Halbout, Martin Sandvoss, Marek J. Pecyna, Katrin Scheibner, Martin Hofrichter
Published in: Journal of Inorganic Biochemistry, 183, 2018, Page(s) 84-93, ISSN 0162-0134
Publisher: Elsevier BV
DOI: 10.1016/j.jinorgbio.2018.03.011

Selective synthesis of the resveratrol analogue 4,4′-dihydroxy- trans -stilbene and stilbenoids modification by fungal peroxygenases

Author(s): Carmen Aranda, René Ullrich, Jan Kiebist, Katrin Scheibner, José C. del Río, Martin Hofrichter, Angel T. Martínez, Ana Gutiérrez
Published in: Catalysis Science & Technology, 8/9, 2018, Page(s) 2394-2401, ISSN 2044-4753
Publisher: Royal Society of Chemistry
DOI: 10.1039/c8cy00272j

Enzymatic Preparation of 2,5-Furandicarboxylic Acid (FDCA)—A Substitute of Terephthalic Acid—By the Joined Action of Three Fungal Enzymes

Author(s): Alexander Karich, Sebastian Kleeberg, René Ullrich, Martin Hofrichter
Published in: Microorganisms, 6/1, 2018, Page(s) 5, ISSN 2076-2607
Publisher: MDPI
DOI: 10.3390/microorganisms6010005

Selective Synthesis of the Human Drug Metabolite 5′-Hydroxypropranolol by an Evolved Self-Sufficient Peroxygenase

Author(s): Patricia Gomez de Santos, Marina Cañellas, Florian Tieves, Sabry H. H. Younes, Patricia Molina-Espeja, Martin Hofrichter, Frank Hollmann, Victor Guallar, Miguel Alcalde
Published in: ACS Catalysis, 2018, Page(s) 4789-4799, ISSN 2155-5435
Publisher: American Chemical Society
DOI: 10.1021/acscatal.8b01004

Draft Genome Sequence of the Sordariomycete Lecythophora ( Coniochaeta ) hoffmannii CBS 245.38

Author(s): Sabrina Leonhardt, Enrico Büttner, Anna Maria Gebauer, Martin Hofrichter, Harald Kellner
Published in: Genome Announcements, 6/7, 2018, Page(s) e01510-17, ISSN 2169-8287
Publisher: American Society for Microbiology
DOI: 10.1128/genomeA.01510-17

Shuffling the neutral drift of unspecific peroxygenase in Saccharomyces cerevisiae

Author(s): Javier Martin-Diaz, Carmen Paret, Eva García-Ruiz, Patricia Molina-Espeja, Miguel Alcalde
Published in: Applied and Environmental Microbiology, 2018, Page(s) AEM.00808-18, ISSN 0099-2240
Publisher: American Society for Microbiology
DOI: 10.1128/AEM.00808-18

Multiple implications of an active site phenylalanine in the catalysis of aryl-alcohol oxidase

Author(s): Juan Carro, Pep Amengual-Rigo, Ferran Sancho, Milagros Medina, Victor Guallar, Patricia Ferreira, Angel T. Martínez
Published in: Scientific Reports, 8/1, 2018, ISSN 2045-2322
Publisher: Nature Publishing Group
DOI: 10.1038/s41598-018-26445-x

Evolutionary convergence in lignin-degrading enzymes

Author(s): Iván Ayuso-Fernández, Francisco J. Ruiz-Dueñas, Angel T. Martínez
Published in: Proceedings of the National Academy of Sciences, 2018, Page(s) 201802555, ISSN 0027-8424
Publisher: National Academy of Sciences
DOI: 10.1073/pnas.1802555115

Role of surface tryptophan for peroxidase oxidation of nonphenolic lignin

Author(s): Verónica Sáez-Jiménez, Jorge Rencoret, Miguel Angel Rodríguez-Carvajal, Ana Gutiérrez, Francisco Javier Ruiz-Dueñas, Angel T. Martínez
Published in: Biotechnology for Biofuels, 9/1, 2016, Page(s) nn, ISSN 1754-6834
Publisher: BioMed Central
DOI: 10.1186/s13068-016-0615-x

Biocatalytic Oxidation Reactions: A Chemist's Perspective

Author(s): JiaJia Dong, Elena Fernández-Fueyo, Frank Hollmann, Caroline E. Paul, Milja Pesic, Sandy Schmidt, Yonghua Wang, Sabry Younes, Wuyuan Zhang
Published in: Angewandte Chemie International Edition, 57/30, 2018, Page(s) 9238-9261, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201800343

Description of a Non-Canonical Mn(II)-Oxidation Site in Peroxidases

Author(s): Elena Fernández-Fueyo, Irene Davó-Siguero, David Almendral, Dolores Linde, Maria Camilla Baratto, Rebecca Pogni, Antonio Romero, Victor Guallar, Angel T. Martínez
Published in: ACS Catalysis, 8/9, 2018, Page(s) 8386-8395, ISSN 2155-5435
Publisher: American Chemical Society
DOI: 10.1021/acscatal.8b02306

Modification of the peroxygenative:peroxidative activity ratio in the unspecific peroxygenase from Agrocybe aegerita by structure-guided evolution

Author(s): Diana M. Mate, Miguel A. Palomino, Patricia Molina-Espeja, Javier Martin-Diaz, Miguel Alcalde
Published in: Protein Engineering Design and Selection, 2017, ISSN 1741-0126
Publisher: Oxford University Press
DOI: 10.1093/protein/gzw073

A peroxygenase from Chaetomium globosum catalyzes the selective oxygenation of testosterone

Author(s): Jan Kiebist, Kai-Uwe Schmidtke, Jörg Zimmermann, Harald Kellner, Nico Jehmlich, René Ullrich, Daniel Zänder, Martin Hofrichter, Katrin Scheibner
Published in: ChemBioChem, 2017, ISSN 1439-4227
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/cbic.201600677

Increase of Redox Potential during the Evolution of Enzymes Degrading Recalcitrant Lignin

Author(s): Iván Ayuso-Fernández, Antonio L. De Lacey, Francisco J. Cañada, Francisco J. Ruiz-Dueñas, Angel T. Martínez
Published in: Chemistry - A European Journal, 25/11, 2019, Page(s) 2708-2712, ISSN 0947-6539
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/chem.201805679

Selective synthesis of 4-hydroxyisophorone and 4-ketoisophorone by fungal peroxygenases

Author(s): Carmen Aranda, Martí Municoy, Víctor Guallar, Jan Kiebist, Katrin Scheibner, René Ullrich, José C. del Río, Martin Hofrichter, Angel T. Martínez, Ana Gutiérrez
Published in: Catalysis Science & Technology, 2019, ISSN 2044-4753
Publisher: Royal Society of Chemistry
DOI: 10.1039/c8cy02114g

Energising the E-factor: The E+-factor

Author(s): Florian Tieves, Fabio Tonin, Elena Fernández-Fueyo, John M. Robbins, Bettina Bommarius, Andreas S. Bommarius, Miguel Alcalde, Frank Hollmann
Published in: Tetrahedron, 75/10, 2019, Page(s) 1311-1314, ISSN 0040-4020
Publisher: Pergamon Press Ltd.
DOI: 10.1016/j.tet.2019.01.065

Structure-Guided Immobilization of an Evolved Unspecific Peroxygenase

Author(s): Patricia Molina-Espeja, Paloma Santos-Moriano, Eva García-Ruiz, Antonio Ballesteros, Francisco Plou, Miguel Alcalde
Published in: International Journal of Molecular Sciences, 20/7, 2019, Page(s) 1627, ISSN 1422-0067
Publisher: Multidisciplinary Digital Publishing Institute (MDPI)
DOI: 10.3390/ijms20071627

Structural Insights into the Substrate Promiscuity of a Laboratory-Evolved Peroxygenase

Author(s): Mercedes Ramirez-Escudero, Patricia Molina-Espeja, Patricia Gomez de Santos, Martin Hofrichter, Julia Sanz-Aparicio, Miguel Alcalde
Published in: ACS Chemical Biology, 13/12, 2018, Page(s) 3259-3268, ISSN 1554-8929
Publisher: American Chemical Society
DOI: 10.1021/acschembio.8b00500

Formate Oxidase (FOx) from Aspergillus oryzae : One Catalyst Enables Diverse H 2 O 2 -Dependent Biocatalytic Oxidation Reactions

Author(s): Florian Tieves, Sébastien Jean-Paul Willot, Morten Martinus Cornelis Harald van Schie, Marine Charlène Renée Rauch, Sabry Hamdy Hamed Younes, Wuyuan Zhang, JiaJia Dong, Patricia Gomez de Santos, John Mick Robbins, Bettina Bommarius, Miguel Alcalde, Andreas Sebastian Bommarius, Frank Hollmann
Published in: Angewandte Chemie International Edition, 58/23, 2019, Page(s) 7873-7877, ISSN 1433-7851
Publisher: John Wiley & Sons Ltd.
DOI: 10.1002/anie.201902380

Experimental recreation of the evolution of lignin-degrading enzymes from the Jurassic to date

Author(s): Iván Ayuso-Fernández, Angel T. Martínez, Francisco J. Ruiz-Dueñas
Published in: Biotechnology for Biofuels, 10/1, 2017, ISSN 1754-6834
Publisher: BioMed Central
DOI: 10.1186/s13068-017-0744-x

Binding and Catalytic Mechanisms of Veratryl Alcohol Oxidation by Lignin Peroxidase: A Theoretical and Experimental Study

Author(s): Jefferson O. Romero, Elena Fernández-Fueyo, Fabián Avila-Salas, Rodrigo Recabarren, Jans Alzate-Morales, Angel T. Martínez
Published in: Computational and Structural Biotechnology Journal, 17, 2019, Page(s) 1066-1074, ISSN 2001-0370
Publisher: Elsevier
DOI: 10.1016/j.csbj.2019.07.002

Peroxidase evolution in white-rot fungi follows wood lignin evolution in plants

Author(s): Iván Ayuso-Fernández, Jorge Rencoret, Ana Gutiérrez, Francisco Javier Ruiz-Dueñas, Angel T. Martínez
Published in: Proceedings of the National Academy of Sciences, 116/36, 2019, Page(s) 17900-17905, ISSN 0027-8424
Publisher: National Academy of Sciences
DOI: 10.1073/pnas.1905040116

Environmental sustainability assessment of HMF and FDCA production from lignocellulosic biomass through life cycle assessment (LCA)

Author(s): Sara Bello, Iana Salim, Pedro Méndez-Trelles, Eva Rodil, Gumersindo Feijoo, Maria Teresa Moreira
Published in: Holzforschung, 73/1, 2018, Page(s) 105-115, ISSN 0018-3830
Publisher: Walter de Gruyter GmbH & Co. KG
DOI: 10.1515/hf-2018-0100

Towards improving the sustainability of bioplastics: Process modelling and life cycle assessment of two separation routes for 2,5-furandicarboxylic acid

Author(s): Sara Bello, Pedro Méndez-Trelles, Eva Rodil, Gumersindo Feijoo, Maria Teresa Moreira
Published in: Separation and Purification Technology, 233, 2020, Page(s) 116056, ISSN 1383-5866
Publisher: Pergamon Press Ltd.
DOI: 10.1016/j.seppur.2019.116056

Complete oxidation of hydroxymethylfurfural to furandicarboxylic acid by aryl-alcohol oxidase

Author(s): Ana Serrano, Eva Calviño, Juan Carro, María I. Sánchez-Ruiz, F. Javier Cañada, Angel T. Martínez
Published in: Biotechnology for Biofuels, 12/1, 2019, ISSN 1754-6834
Publisher: BioMed Central
DOI: 10.1186/s13068-019-1555-z

Sequential oxidation of 5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid by an evolved aryl-alcohol oxidase

Author(s): Javier Viña-Gonzalez, Angel T. Martinez, Victor Guallar, Miguel Alcalde
Published in: Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, 1868/1, 2020, Page(s) 140293, ISSN 1570-9639
Publisher: Elsevier BV
DOI: 10.1016/j.bbapap.2019.140293

Selective Oxygenation of Ionones and Damascones by Fungal Peroxygenases

Author(s): Esteban D. Babot, Carmen Aranda, José C. del Rı́o, René Ullrich, Jan Kiebist, Katrin Scheibner, Martin Hofrichter, Angel T. Martı́nez, Ana Gutiérrez
Published in: Journal of Agricultural and Food Chemistry, 68/19, 2020, Page(s) 5375-5383, ISSN 0021-8561
Publisher: American Chemical Society
DOI: 10.1021/acs.jafc.0c01019

Biological Lignin Degradation

Author(s): A. T. Martínez, S. Camarero, F. J. Ruiz-Dueñas, M. J. Martínez
Published in: Lignin Valorization: Emerging Approaches, 2018, Page(s) 199-225, ISBN 978-1-78262-554-4
Publisher: Royal Society of Chemistry
DOI: 10.1039/9781788010351-00199

Directed Evolution of Unspecific 5 Peroxygenase

Author(s): Patricia Molina-Espeja, Patricia Gómez de Santos, Miguel Alcalde
Published in: Directed Enzyme Evolution: Advances and Applications, 2017, Page(s) 127-143, ISBN 978-3-319-50411-7
Publisher: Springer International Publishing
DOI: 10.1007/978-3-319-50413-1_5

Nuevas reacciones de interés industrial con peroxigenasas fúngicas

Author(s): Olmedo, Andrés
Published in: 2018
Publisher: CSIC - Instituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS) / Universidad de Sevilla

Nuevas oxidorreductasas GMC de basidiomicetos ligninolíticos: Screening genómico, mecanismo catalítico y potencial biotecnológico

Author(s): Juan R. Carro Aramburu
Published in: 2017
Publisher: CSIC - Centro de Investigaciones Biológicas (CIB) / Universidad Complutense de Madrid

Biotransformations of industrial interest catalyzed by fungal peroxygenases

Author(s): Carmen Aranda
Published in: 2019
Publisher: IRNAS-CSIC/Universidad de Sevilla

Resurrection of ancestral ligninolytic peroxidases Resurrección de peroxidasas ligninolíticas ancestrales

Author(s): Ivan Ayuso
Published in: 2019
Publisher: CIB-CSIC/Universidad Complutense de Madrid

Biotechnology platforms for aryl-alcohol oxidases by directed evolution

Author(s): Javier Viña
Published in: 2019
Publisher: ICP-CSIC/Universidad Autónoma de Madrid

Evolución dirigida de la peroxigenasa inespecífica de agrocybe aegerita: tolerancia a disolventes orgánicos mediante deriva genética neutral y evolución adaptativa

Author(s): Javier Martin
Published in: 2019
Publisher: ICP-CSIC/Universidad Autónoma de Madrid

Oxyfunktionalisierung pharmazeutisch relevanter Strukturen durch unspezifische Peroxygenasen der Familie I aus Dikarya-Pilzen

Author(s): Jan Kiebist
Published in: 2018
Publisher: Technical University of Dresden

Datasets

MOESM2 of Experimental recreation of the evolution of lignin-degrading enzymes from the Jurassic to date

Author(s): Ayuso-Fernández, Iván; Martínez, Angel; Ruiz-Dueñas, Francisco
Published in: Figshare