5-hydroxymethylfurfural conversion by fungal aryl-alcohol oxidase and unspecific peroxygenase
Financiación FP7 / Fp7 Funds
Resumen: Oxidative 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.
Idioma: Inglés
DOI: 10.1111/febs.13177
Año: 2015
Publicado en: FEBS JOURNAL 282, 16 (2015), 3218–3229
ISSN: 1742-464X

Factor impacto JCR: 4.237 (2015)
Categ. JCR: BIOCHEMISTRY & MOLECULAR BIOLOGY rank: 72 / 289 = 0.249 (2015) - Q1 - T1
Factor impacto SCIMAGO: 2.152 - Biochemistry (Q1) - Molecular Biology (Q1) - Cell Biology (Q1)

Financiación: info:eu-repo/grantAgreement/EC/FP7/613549/EU/Optimized oxidoreductases for medium and large scale industrial biotransformations/INDOX
Financiación: info:eu-repo/grantAgreement/ES/MICINN/BIO2011-26694
Tipo y forma: Article (Published version)
Área (Departamento): Área Bioquímica y Biolog.Mole. (Dpto. Bioq.Biolog.Mol. Celular)

Creative Commons You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. If you remix, transform, or build upon the material, you may not distribute the modified material.


Exportado de SIDERAL (2021-01-21-10:53:57)


Visitas y descargas

Este artículo se encuentra en las siguientes colecciones:
Articles



 Record created 2017-09-21, last modified 2021-01-21


Versión publicada:
 PDF
Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)