Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural
Abstract Background 2,5-Furandicarboxylic acid is a renewable building block for the production of polyfurandicarboxylates, which are biodegradable polyesters expected to substitute their classical counterparts derived from fossil resources. It may be produced from bio-based 5-hydroxymethylfurfural...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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BMC
2018-04-01
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| Series: | Biotechnology for Biofuels |
| Subjects: | |
| Online Access: | http://link.springer.com/article/10.1186/s13068-018-1091-2 |
| _version_ | 1811232735607390208 |
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| author | Juan Carro Elena Fernández-Fueyo Carmen Fernández-Alonso Javier Cañada René Ullrich Martin Hofrichter Miguel Alcalde Patricia Ferreira Angel T. Martínez |
| author_facet | Juan Carro Elena Fernández-Fueyo Carmen Fernández-Alonso Javier Cañada René Ullrich Martin Hofrichter Miguel Alcalde Patricia Ferreira Angel T. Martínez |
| author_sort | Juan Carro |
| collection | DOAJ |
| description | Abstract Background 2,5-Furandicarboxylic acid is a renewable building block for the production of polyfurandicarboxylates, which are biodegradable polyesters expected to substitute their classical counterparts derived from fossil resources. It may be produced from bio-based 5-hydroxymethylfurfural or 5-methoxymethylfurfural, both obtained by the acidic dehydration of biomass-derived fructose. 5-Methoxymethylfurfural, which is produced in the presence of methanol, generates less by-products and exhibits better storage stability than 5-hydroxymethylfurfural being, therefore, the industrial substrate of choice. Results In this work, an enzymatic cascade involving three fungal oxidoreductases has been developed for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural. Aryl-alcohol oxidase and unspecific peroxygenase act on 5-methoxymethylfurfural and its partially oxidized derivatives yielding 2,5-furandicarboxylic acid, as well as methanol as a by-product. Methanol oxidase takes advantage of the methanol released for in situ producing H2O2 that, along with that produced by aryl-alcohol oxidase, fuels the peroxygenase reactions. In this way, the enzymatic cascade proceeds independently, with the only input of atmospheric O2, to attain a 70% conversion of initial 5-methoxymethylfurfural. The addition of some exogenous methanol to the reaction further improves the yield to attain an almost complete conversion of 5-methoxymethylfurfural into 2,5-furandicarboxylic acid. Conclusions The synergistic action of aryl-alcohol oxidase and unspecific peroxygenase in the presence of 5-methoxymethylfurfural and O2 is sufficient for the production of 2,5-furandicarboxylic acid. The addition of methanol oxidase to the enzymatic cascade increases the 2,5-furandicarboxylic acid yields by oxidizing a reaction by-product to fuel the peroxygenase reactions. |
| first_indexed | 2024-04-12T11:09:12Z |
| format | Article |
| id | doaj.art-7c2a800f778e4028bcc3d0ade7fcd196 |
| institution | Directory Open Access Journal |
| issn | 1754-6834 |
| language | English |
| last_indexed | 2024-04-12T11:09:12Z |
| publishDate | 2018-04-01 |
| publisher | BMC |
| record_format | Article |
| series | Biotechnology for Biofuels |
| spelling | doaj.art-7c2a800f778e4028bcc3d0ade7fcd1962022-12-22T03:35:40ZengBMCBiotechnology for Biofuels1754-68342018-04-0111111010.1186/s13068-018-1091-2Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfuralJuan Carro0Elena Fernández-Fueyo1Carmen Fernández-Alonso2Javier Cañada3René Ullrich4Martin Hofrichter5Miguel Alcalde6Patricia Ferreira7Angel T. Martínez8Centro de Investigaciones Biológicas, CSICCentro de Investigaciones Biológicas, CSICCentro de Investigaciones Biológicas, CSICCentro de Investigaciones Biológicas, CSICDepartment of Bio- and Environmental Sciences, International Institute Zittau - Technische Universität DresdenDepartment of Bio- and Environmental Sciences, International Institute Zittau - Technische Universität DresdenDepartment of Biocatalysis, Institute of Catalysis, CSICDepartment of Biochemistry and Molecular and Cellular Biology and BIFI, University of ZaragozaCentro de Investigaciones Biológicas, CSICAbstract Background 2,5-Furandicarboxylic acid is a renewable building block for the production of polyfurandicarboxylates, which are biodegradable polyesters expected to substitute their classical counterparts derived from fossil resources. It may be produced from bio-based 5-hydroxymethylfurfural or 5-methoxymethylfurfural, both obtained by the acidic dehydration of biomass-derived fructose. 5-Methoxymethylfurfural, which is produced in the presence of methanol, generates less by-products and exhibits better storage stability than 5-hydroxymethylfurfural being, therefore, the industrial substrate of choice. Results In this work, an enzymatic cascade involving three fungal oxidoreductases has been developed for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural. Aryl-alcohol oxidase and unspecific peroxygenase act on 5-methoxymethylfurfural and its partially oxidized derivatives yielding 2,5-furandicarboxylic acid, as well as methanol as a by-product. Methanol oxidase takes advantage of the methanol released for in situ producing H2O2 that, along with that produced by aryl-alcohol oxidase, fuels the peroxygenase reactions. In this way, the enzymatic cascade proceeds independently, with the only input of atmospheric O2, to attain a 70% conversion of initial 5-methoxymethylfurfural. The addition of some exogenous methanol to the reaction further improves the yield to attain an almost complete conversion of 5-methoxymethylfurfural into 2,5-furandicarboxylic acid. Conclusions The synergistic action of aryl-alcohol oxidase and unspecific peroxygenase in the presence of 5-methoxymethylfurfural and O2 is sufficient for the production of 2,5-furandicarboxylic acid. The addition of methanol oxidase to the enzymatic cascade increases the 2,5-furandicarboxylic acid yields by oxidizing a reaction by-product to fuel the peroxygenase reactions.http://link.springer.com/article/10.1186/s13068-018-1091-22,5-Furandicarboxylic acid5-Methoxymethyl furfuralEnzyme cascadeBiocatalysisOxidasePeroxygenase |
| spellingShingle | Juan Carro Elena Fernández-Fueyo Carmen Fernández-Alonso Javier Cañada René Ullrich Martin Hofrichter Miguel Alcalde Patricia Ferreira Angel T. Martínez Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural Biotechnology for Biofuels 2,5-Furandicarboxylic acid 5-Methoxymethyl furfural Enzyme cascade Biocatalysis Oxidase Peroxygenase |
| title | Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural |
| title_full | Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural |
| title_fullStr | Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural |
| title_full_unstemmed | Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural |
| title_short | Self-sustained enzymatic cascade for the production of 2,5-furandicarboxylic acid from 5-methoxymethylfurfural |
| title_sort | self sustained enzymatic cascade for the production of 2 5 furandicarboxylic acid from 5 methoxymethylfurfural |
| topic | 2,5-Furandicarboxylic acid 5-Methoxymethyl furfural Enzyme cascade Biocatalysis Oxidase Peroxygenase |
| url | http://link.springer.com/article/10.1186/s13068-018-1091-2 |
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