Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks
ABSTRACT Enzyme‐catalyzed transformations have a great potential in both the pharmaceutical and chemical industry to achieve complex and (stereo)selective synthesis under mild reaction conditions. Still, the implementation of biocatalysis in the prerequisite upgrading of inert synthons into activate...
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crwiley:10.1002/app.48949 2024-06-02T07:56:43+00:00 Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks Farhat, Wissam Biundo, Antonino Stamm, Arne Malmström, Eva Syrén, Per‐Olof Stiftelsen Lantbruksforskning Vetenskapsrådet 2020 http://dx.doi.org/10.1002/app.48949 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fapp.48949 https://onlinelibrary.wiley.com/doi/pdf/10.1002/app.48949 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/app.48949 en eng Wiley http://creativecommons.org/licenses/by-nc-nd/4.0/ Journal of Applied Polymer Science volume 137, issue 18 ISSN 0021-8995 1097-4628 journal-article 2020 crwiley https://doi.org/10.1002/app.48949 2024-05-06T07:01:38Z ABSTRACT Enzyme‐catalyzed transformations have a great potential in both the pharmaceutical and chemical industry to achieve complex and (stereo)selective synthesis under mild reaction conditions. Still, the implementation of biocatalysis in the prerequisite upgrading of inert synthons into activated monomers for polymer applications has not yet been fully realized. In this contribution, we show that scaled‐up synthesis of bicyclic norcamphor lactone using an engineered Baeyer–Villiger monooxygenase (BVMO) is feasible to reach complete conversion of the corresponding ketone in 24 h in shake‐flask. The lactone monomer obtained by enzyme catalysis was copolymerized with ε‐caprolactone via ring‐opening polymerization to study the impact of the additional ring on material properties. Moreover, four‐arm star‐like, homo and block copolymers were designed from ε‐caprolactone, ε‐decalactone, and norcamphor lactone and characterized for their structural and thermal properties. These newly explored macromolecules were functionalized with furan rings using the enzyme Candida antarctica lipase B which allowed the formation of thermolabile networks via the pericyclic reaction with bismaleimide by means of Diels–Alder chemistry. The bonding/debonding state of these star‐like based materials can be tuned by a suitable selection of thermal treatment. The temperature‐dependent reversibility was assessed by thermal analysis and solubility test. Our results presented here shed light on the high potential of the use of chemoenzymatic approaches in the synthesis of new functional materials with tuned physiochemical properties. © 2020 The Authors. Journal of Applied Polymer Science published by Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020 , 137 , 48949. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of Applied Polymer Science 137 18 |
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English |
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ABSTRACT Enzyme‐catalyzed transformations have a great potential in both the pharmaceutical and chemical industry to achieve complex and (stereo)selective synthesis under mild reaction conditions. Still, the implementation of biocatalysis in the prerequisite upgrading of inert synthons into activated monomers for polymer applications has not yet been fully realized. In this contribution, we show that scaled‐up synthesis of bicyclic norcamphor lactone using an engineered Baeyer–Villiger monooxygenase (BVMO) is feasible to reach complete conversion of the corresponding ketone in 24 h in shake‐flask. The lactone monomer obtained by enzyme catalysis was copolymerized with ε‐caprolactone via ring‐opening polymerization to study the impact of the additional ring on material properties. Moreover, four‐arm star‐like, homo and block copolymers were designed from ε‐caprolactone, ε‐decalactone, and norcamphor lactone and characterized for their structural and thermal properties. These newly explored macromolecules were functionalized with furan rings using the enzyme Candida antarctica lipase B which allowed the formation of thermolabile networks via the pericyclic reaction with bismaleimide by means of Diels–Alder chemistry. The bonding/debonding state of these star‐like based materials can be tuned by a suitable selection of thermal treatment. The temperature‐dependent reversibility was assessed by thermal analysis and solubility test. Our results presented here shed light on the high potential of the use of chemoenzymatic approaches in the synthesis of new functional materials with tuned physiochemical properties. © 2020 The Authors. Journal of Applied Polymer Science published by Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020 , 137 , 48949. |
author2 |
Stiftelsen Lantbruksforskning Vetenskapsrådet |
format |
Article in Journal/Newspaper |
author |
Farhat, Wissam Biundo, Antonino Stamm, Arne Malmström, Eva Syrén, Per‐Olof |
spellingShingle |
Farhat, Wissam Biundo, Antonino Stamm, Arne Malmström, Eva Syrén, Per‐Olof Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
author_facet |
Farhat, Wissam Biundo, Antonino Stamm, Arne Malmström, Eva Syrén, Per‐Olof |
author_sort |
Farhat, Wissam |
title |
Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
title_short |
Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
title_full |
Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
title_fullStr |
Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
title_full_unstemmed |
Lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
title_sort |
lactone monomers obtained by enzyme catalysis and their use in reversible thermoresponsive networks |
publisher |
Wiley |
publishDate |
2020 |
url |
http://dx.doi.org/10.1002/app.48949 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fapp.48949 https://onlinelibrary.wiley.com/doi/pdf/10.1002/app.48949 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/app.48949 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of Applied Polymer Science volume 137, issue 18 ISSN 0021-8995 1097-4628 |
op_rights |
http://creativecommons.org/licenses/by-nc-nd/4.0/ |
op_doi |
https://doi.org/10.1002/app.48949 |
container_title |
Journal of Applied Polymer Science |
container_volume |
137 |
container_issue |
18 |
_version_ |
1800758251218796544 |