5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase

12 páginas.-- 6 figuras.-- 2 tablas.-- 34 referencias.-- Additional supporting information may be found in the online version of this article at the publisher’s web site: Fig. S1. GC-MS analysis of standard compounds. Fig. S2. 1H-NMR spectra for HMF, DFF and FFCA in DMSO-d6. Table S1. Kinetic consta...

Descripción completa

Detalles Bibliográficos
Autores: Carro, Juan, Ferreira, Patricia, Rodríguez, Leonor, Prieto Orzanco, Alicia, Serrano, Ana, Balcells, Beatriz, Ardá, Ana, Jiménez-Barbero, Jesús, Gutiérrez Suárez, Ana, Martínez, Ángel T.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/121504
Acceso en línea:http://hdl.handle.net/10261/121504
Access Level:acceso abierto
Palabra clave:2,5-formylfurancarboxylic acid
2,5-furandicarboxylic acid
5-hydroxymethylfurfural
Aryl-alcohol oxidase
Unspecific peroxygenase
id ES_d97e49acae071a8f4e995d6d5f5642bc
oai_identifier_str oai:digital.csic.es:10261/121504
network_acronym_str ES
network_name_str España
repository_id_str
spelling 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenaseCarro, JuanFerreira, PatriciaRodríguez, LeonorPrieto Orzanco, AliciaSerrano, AnaBalcells, BeatrizArdá, AnaJiménez-Barbero, JesúsGutiérrez Suárez, AnaMartínez, Ángel T.2,5-formylfurancarboxylic acid2,5-furandicarboxylic acid5-hydroxymethylfurfuralAryl-alcohol oxidaseUnspecific peroxygenase12 páginas.-- 6 figuras.-- 2 tablas.-- 34 referencias.-- Additional supporting information may be found in the online version of this article at the publisher’s web site: Fig. S1. GC-MS analysis of standard compounds. Fig. S2. 1H-NMR spectra for HMF, DFF and FFCA in DMSO-d6. Table S1. Kinetic constants for a variety of AAO substrates. Doc. S1. MS identification of products from HMF conversion into FDCA. FEBSOxidative conversion of 5-hydroxymethylfurfural (HMF) is of biotechnological interest for the production of renewable (lignocellulose-based) platform chemicals, such as 2,5-furandicarboxylic acid (FDCA). To the best of our knowledge, the ability of fungal aryl-alcohol oxidase (AAO) to oxidize HMF is reported here for the first time, resulting in almost complete conversion into 2,5-formylfurancarboxylic acid (FFCA) in a few hours. The reaction starts with alcohol oxidation, yielding 2,5-diformylfuran (DFF), which is rapidly converted into FFCA by carbonyl oxidation, most probably without leaving the enzyme active site. This agrees with the similar catalytic efficiencies of the enzyme with respect to oxidization of HMF and DFF, and its very low activity on 2,5-hydroxymethylfurancarboxylic acid (which was not detected by GC-MS). However, AAO was found to be unable to directly oxidize the carbonyl group in FFCA, and only modest amounts of FDCA are formed from HMF (most probably by chemical oxidation of FFCA by the H2O2 previously generated by AAO). As aldehyde oxidation by AAO proceeds via the corresponding geminal diols (aldehyde hydrates), the various carbonyl oxidation rates may be related to the low degree of hydration of FFCA compared with DFF. The conversion of HMF was completed by introducing a fungal unspecific heme peroxygenase that uses the H2O2 generated by AAO to transform FFCA into FDCA, albeit more slowly than the previous AAO reactions. By adding this peroxygenase when FFCA production by AAO has been completed, transformation of HMF into FDCA may be achieved in a reaction cascade in which O2 is the only co-substrate required, and water is the only by-product formed. © 2014 The Authors. FEBS Journal published by John Wiley & Sons Ltd on behalf of FEBS.This work was supported by the HIPOP Project (BIO2011-26694) of the Spanish Ministerio de Economía y Competitividad, co-financed by the Fonds Europeen de Developpement Regional, and the European INDOX project (KBBE-2013-7-613549). J.C. acknowledges a Formación del Profesorado Universitario Fellowship (AP2012-2041) from the Spanish Ministerio de Educación, Cultura y Deporte. The authors thank Pedro Merino (Department of Organic Chemistry, University of Zaragoza, Spain) for inspiring suggestions.Peer reviewedJohn Wiley & SonsMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2015info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/121504reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Ingléshttp://dx.doi.org/10.1111/febs.13177Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1215042026-05-22T06:33:51Z
dc.title.none.fl_str_mv 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
title 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
spellingShingle 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
Carro, Juan
2,5-formylfurancarboxylic acid
2,5-furandicarboxylic acid
5-hydroxymethylfurfural
Aryl-alcohol oxidase
Unspecific peroxygenase
title_short 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
title_full 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
title_fullStr 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
title_full_unstemmed 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
title_sort 5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
dc.creator.none.fl_str_mv Carro, Juan
Ferreira, Patricia
Rodríguez, Leonor
Prieto Orzanco, Alicia
Serrano, Ana
Balcells, Beatriz
Ardá, Ana
Jiménez-Barbero, Jesús
Gutiérrez Suárez, Ana
Martínez, Ángel T.
author Carro, Juan
author_facet Carro, Juan
Ferreira, Patricia
Rodríguez, Leonor
Prieto Orzanco, Alicia
Serrano, Ana
Balcells, Beatriz
Ardá, Ana
Jiménez-Barbero, Jesús
Gutiérrez Suárez, Ana
Martínez, Ángel T.
author_role author
author2 Ferreira, Patricia
Rodríguez, Leonor
Prieto Orzanco, Alicia
Serrano, Ana
Balcells, Beatriz
Ardá, Ana
Jiménez-Barbero, Jesús
Gutiérrez Suárez, Ana
Martínez, Ángel T.
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv 2,5-formylfurancarboxylic acid
2,5-furandicarboxylic acid
5-hydroxymethylfurfural
Aryl-alcohol oxidase
Unspecific peroxygenase
topic 2,5-formylfurancarboxylic acid
2,5-furandicarboxylic acid
5-hydroxymethylfurfural
Aryl-alcohol oxidase
Unspecific peroxygenase
description 12 páginas.-- 6 figuras.-- 2 tablas.-- 34 referencias.-- Additional supporting information may be found in the online version of this article at the publisher’s web site: Fig. S1. GC-MS analysis of standard compounds. Fig. S2. 1H-NMR spectra for HMF, DFF and FFCA in DMSO-d6. Table S1. Kinetic constants for a variety of AAO substrates. Doc. S1. MS identification of products from HMF conversion into FDCA. FEBS
publishDate 2015
dc.date.none.fl_str_mv 2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/121504
url http://hdl.handle.net/10261/121504
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv http://dx.doi.org/10.1111/febs.13177
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869421391961391105
score 15.81155

Similares en LA Referencia