Enzyme-Catalyzed Oxidation of 5-Hydroxymethylfurfural to Furan-2,5-dicarboxylic Acid
Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5‐hydroxymethylfurfural (HMF). Recently we identified an FAD‐dependent enzyme which...
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Published in | Angewandte Chemie (International ed.) Vol. 53; no. 25; pp. 6515 - 6518 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
16.06.2014
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
Edition | International ed. in English |
Subjects | |
Online Access | Get full text |
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Abstract | Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5‐hydroxymethylfurfural (HMF). Recently we identified an FAD‐dependent enzyme which is active towards HMF and related compounds. This oxidase has the remarkable capability of oxidizing [5‐(hydroxymethyl)furan‐2‐yl]methanol to FDCA, a reaction involving four consecutive oxidations. The oxidase can produce FDCA from HMF with high yield at ambient temperature and pressure. Examination of the underlying mechanism shows that the oxidase acts on alcohol groups only and depends on the hydration of aldehydes for the oxidation reaction required to form FDCA.
A fourpeat: The recently discovered 5‐hydroxymethylfurfural oxidase (HMFO) was found to perform a quadruple oxidation of [5‐(hydroxymethyl)furan‐2‐yl]methanol (see scheme). The biocatalyst can also be used to convert 5‐hydroxymethylfurfural into furan‐2,5‐dicarboxylic acid, thus providing a biobased platform chemical for the production of polymers. The oxidase acts on alcohol groups only and therefore depends on the hydration of aldehyde groups. |
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AbstractList | Furan-2,5-dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5-hydroxymethylfurfural (HMF). Recently we identified an FAD-dependent enzyme which is active towards HMF and related compounds. This oxidase has the remarkable capability of oxidizing [5-(hydroxymethyl)furan-2-yl]methanol to FDCA, a reaction involving four consecutive oxidations. The oxidase can produce FDCA from HMF with high yield at ambient temperature and pressure. Examination of the underlying mechanism shows that the oxidase acts on alcohol groups only and depends on the hydration of aldehydes for the oxidation reaction required to form FDCA. Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5‐hydroxymethylfurfural (HMF). Recently we identified an FAD‐dependent enzyme which is active towards HMF and related compounds. This oxidase has the remarkable capability of oxidizing [5‐(hydroxymethyl)furan‐2‐yl]methanol to FDCA, a reaction involving four consecutive oxidations. The oxidase can produce FDCA from HMF with high yield at ambient temperature and pressure. Examination of the underlying mechanism shows that the oxidase acts on alcohol groups only and depends on the hydration of aldehydes for the oxidation reaction required to form FDCA. A fourpeat: The recently discovered 5‐hydroxymethylfurfural oxidase (HMFO) was found to perform a quadruple oxidation of [5‐(hydroxymethyl)furan‐2‐yl]methanol (see scheme). The biocatalyst can also be used to convert 5‐hydroxymethylfurfural into furan‐2,5‐dicarboxylic acid, thus providing a biobased platform chemical for the production of polymers. The oxidase acts on alcohol groups only and therefore depends on the hydration of aldehyde groups. Furan-2,5-dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5-hydroxymethylfurfural (HMF). Recently we identified an FAD-dependent enzyme which is active towards HMF and related compounds. This oxidase has the remarkable capability of oxidizing [5-(hydroxymethyl)furan-2-yl]methanol to FDCA, a reaction involving four consecutive oxidations. The oxidase can produce FDCA from HMF with high yield at ambient temperature and pressure. Examination of the underlying mechanism shows that the oxidase acts on alcohol groups only and depends on the hydration of aldehydes for the oxidation reaction required to form FDCA. A fourpeat: The recently discovered 5-hydroxymethylfurfural oxidase (HMFO) was found to perform a quadruple oxidation of [5-(hydroxymethyl)furan-2-yl]methanol (see scheme). The biocatalyst can also be used to convert 5-hydroxymethylfurfural into furan-2,5-dicarboxylic acid, thus providing a biobased platform chemical for the production of polymers. The oxidase acts on alcohol groups only and therefore depends on the hydration of aldehyde groups. Abstract Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes have been reported on the synthesis of FDCA by oxidation of 5‐hydroxymethylfurfural (HMF). Recently we identified an FAD‐dependent enzyme which is active towards HMF and related compounds. This oxidase has the remarkable capability of oxidizing [5‐(hydroxymethyl)furan‐2‐yl]methanol to FDCA, a reaction involving four consecutive oxidations. The oxidase can produce FDCA from HMF with high yield at ambient temperature and pressure. Examination of the underlying mechanism shows that the oxidase acts on alcohol groups only and depends on the hydration of aldehydes for the oxidation reaction required to form FDCA. |
Author | Dijkman, Willem P. Fraaije, Marco W. Groothuis, Daphne E. |
Author_xml | – sequence: 1 givenname: Willem P. surname: Dijkman fullname: Dijkman, Willem P. organization: Molecular Enzymology Group, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, Groningen (The Netherlands) http://www.rug.nl/staff/m.w.fraaije/research – sequence: 2 givenname: Daphne E. surname: Groothuis fullname: Groothuis, Daphne E. organization: Molecular Enzymology Group, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, Groningen (The Netherlands) http://www.rug.nl/staff/m.w.fraaije/research – sequence: 3 givenname: Marco W. surname: Fraaije fullname: Fraaije, Marco W. email: m.w.fraaije@rug.nl organization: Molecular Enzymology Group, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, Groningen (The Netherlands) http://www.rug.nl/staff/m.w.fraaije/research |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24802551$$D View this record in MEDLINE/PubMed |
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ContentType | Journal Article |
Copyright | 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Copyright Wiley Subscription Services, Inc. Jun 2014 |
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Keywords | oxidation enzyme catalysis kinetics biocatalysis carboxylic acids |
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Notes | ArticleID:ANIE201402904 Dutch Ministry of Economic Affairs, Agriculture, and Innovation (EL&I) This work was carried out within the BE-Basic R&D Program, for which an FES subsidy was granted from the Dutch Ministry of Economic Affairs, Agriculture, and Innovation (EL&I). istex:4BABB5F885FD9C480D8440FF165962C92ACFA3B5 ark:/67375/WNG-FH20JJ5L-N This work was carried out within the BE‐Basic R&D Program, for which an FES subsidy was granted from the Dutch Ministry of Economic Affairs, Agriculture, and Innovation (EL&I). ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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Snippet | Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes... Furan-2,5-dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical routes... Abstract Furan‐2,5‐dicarboxylic acid (FDCA) is a biobased platform chemical for the production of polymers. In the past few years, numerous multistep chemical... |
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SubjectTerms | Alcohols Aldehydes Ambient temperature biocatalysis carboxylic acids Catalysis Dicarboxylic acids Dicarboxylic Acids - chemistry enzyme catalysis Enzymes Flavin-adenine dinucleotide Furaldehyde - analogs & derivatives Furaldehyde - chemistry Furans - chemistry Hydration Hydroxymethylfurfural kinetics Molecular Structure Oxidase Oxidation Oxidation-Reduction Oxidoreductases - chemistry Oxidoreductases - metabolism Platforms Polymers Synthesis |
Title | Enzyme-Catalyzed Oxidation of 5-Hydroxymethylfurfural to Furan-2,5-dicarboxylic Acid |
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