Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases
Building blocks with amine functionality are crucial in the chemical industry. Biocatalytic syntheses and chemicals derived from renewable resources are increasingly desired to achieve sustainable production of these amines. As a result, renewable materials such as furfurals, especially furfurylamin...
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MDPI AG
2023-05-01
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| Online Access: | https://www.mdpi.com/2073-4344/13/5/875 |
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| author | Tobias Heinks Luisa M. Merz Jan Liedtke Matthias Höhne Luuk M. van Langen Uwe T. Bornscheuer Gabriele Fischer von Mollard Per Berglund |
| author_facet | Tobias Heinks Luisa M. Merz Jan Liedtke Matthias Höhne Luuk M. van Langen Uwe T. Bornscheuer Gabriele Fischer von Mollard Per Berglund |
| author_sort | Tobias Heinks |
| collection | DOAJ |
| description | Building blocks with amine functionality are crucial in the chemical industry. Biocatalytic syntheses and chemicals derived from renewable resources are increasingly desired to achieve sustainable production of these amines. As a result, renewable materials such as furfurals, especially furfurylamines like 5-(hydroxymethyl)furfurylamine (HMFA) and 2,5-di(aminomethyl)furan (DAF), are gaining increasing attention. In this study, we identified four different amine transaminases (ATAs) that catalyze the reductive amination of 5-(hydroxymethyl)furfural (HMF) and 2,5-diformylfuran (DFF). We successfully immobilized these ATAs on glutaraldehyde-functionalized amine beads using multiple binding and on amine beads by site-selective binding of the unique Cα-formylglycine within an aldehyde tag. All immobilized ATAs were efficiently reused in five repetitive cycles of reductive amination of HMF with alanine as co-substrate, while the ATA from <i>Silicibacter pomeroyi</i> (ATA-Spo) also exhibited high stability for reuse when isopropylamine was used as an amine donor. Additionally, immobilized ATA-Spo yielded high conversion in the batch syntheses of HMFA and DAF using alanine (87% and 87%, respectively) or isopropylamine (99% and 98%, respectively) as amine donors. We further demonstrated that ATA-Spo was effective for the reductive amination of HMF with alanine or isopropylamine in continuous-flow catalysis with high conversion up to 12 days (48% and 41%, respectively). |
| first_indexed | 2024-03-11T03:52:00Z |
| format | Article |
| id | doaj.art-b559d379a8b34402b2834f5acafa4d07 |
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| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-11T03:52:00Z |
| publishDate | 2023-05-01 |
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| series | Catalysts |
| spelling | doaj.art-b559d379a8b34402b2834f5acafa4d072023-11-18T00:51:31ZengMDPI AGCatalysts2073-43442023-05-0113587510.3390/catal13050875Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine TransaminasesTobias Heinks0Luisa M. Merz1Jan Liedtke2Matthias Höhne3Luuk M. van Langen4Uwe T. Bornscheuer5Gabriele Fischer von Mollard6Per Berglund7Faculty of Chemistry, Biochemistry, Bielefeld University, Universitätsstr. 25, 33615 Bielefeld, GermanyDepartment of Industrial Biotechnology, KTH Royal Institute of Technology, AlbaNova University Center, SE-106 91 Stockholm, SwedenFaculty of Chemistry, Biochemistry, Bielefeld University, Universitätsstr. 25, 33615 Bielefeld, GermanyBiocatalysis/Biological Chemistry, Technical University Berlin, Müller-Breslau-Str.10, 10623 Berlin, GermanyViaZym B.V., Molengraaffsingel 10, 2629JD Delft, The NetherlandsDepartment of Biotechnology and Enzyme Catalysis, Institute of Biochemistry, University of Greifswald, Felix Hausdorff-Str. 4, 17487 Greifswald, GermanyFaculty of Chemistry, Biochemistry, Bielefeld University, Universitätsstr. 25, 33615 Bielefeld, GermanyDepartment of Industrial Biotechnology, KTH Royal Institute of Technology, AlbaNova University Center, SE-106 91 Stockholm, SwedenBuilding blocks with amine functionality are crucial in the chemical industry. Biocatalytic syntheses and chemicals derived from renewable resources are increasingly desired to achieve sustainable production of these amines. As a result, renewable materials such as furfurals, especially furfurylamines like 5-(hydroxymethyl)furfurylamine (HMFA) and 2,5-di(aminomethyl)furan (DAF), are gaining increasing attention. In this study, we identified four different amine transaminases (ATAs) that catalyze the reductive amination of 5-(hydroxymethyl)furfural (HMF) and 2,5-diformylfuran (DFF). We successfully immobilized these ATAs on glutaraldehyde-functionalized amine beads using multiple binding and on amine beads by site-selective binding of the unique Cα-formylglycine within an aldehyde tag. All immobilized ATAs were efficiently reused in five repetitive cycles of reductive amination of HMF with alanine as co-substrate, while the ATA from <i>Silicibacter pomeroyi</i> (ATA-Spo) also exhibited high stability for reuse when isopropylamine was used as an amine donor. Additionally, immobilized ATA-Spo yielded high conversion in the batch syntheses of HMFA and DAF using alanine (87% and 87%, respectively) or isopropylamine (99% and 98%, respectively) as amine donors. We further demonstrated that ATA-Spo was effective for the reductive amination of HMF with alanine or isopropylamine in continuous-flow catalysis with high conversion up to 12 days (48% and 41%, respectively).https://www.mdpi.com/2073-4344/13/5/875amine transaminasebiocatalysisDFFflow synthesisHMFimmobilization |
| spellingShingle | Tobias Heinks Luisa M. Merz Jan Liedtke Matthias Höhne Luuk M. van Langen Uwe T. Bornscheuer Gabriele Fischer von Mollard Per Berglund Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases Catalysts amine transaminase biocatalysis DFF flow synthesis HMF immobilization |
| title | Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases |
| title_full | Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases |
| title_fullStr | Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases |
| title_full_unstemmed | Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases |
| title_short | Biosynthesis of Furfurylamines in Batch and Continuous Flow by Immobilized Amine Transaminases |
| title_sort | biosynthesis of furfurylamines in batch and continuous flow by immobilized amine transaminases |
| topic | amine transaminase biocatalysis DFF flow synthesis HMF immobilization |
| url | https://www.mdpi.com/2073-4344/13/5/875 |
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