Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone
Developments of past years placed the bio-based polyesters as competitive substitutes for fossil-based polymers. Moreover, enzymatic polymerization using lipase catalysts has become an important green alternative to chemical polymerization for the synthesis of polyesters with biomedical applications...
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ftunivwagenin:oai:library.wur.nl:wurpubs/538528 2024-01-14T09:59:30+01:00 Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone Todea, Anamaria Aparaschivei, Diana Badea, Valentin Boeriu, Carmen G. Peter, Francisc 2018 application/pdf https://research.wur.nl/en/publications/biocatalytic-route-for-the-synthesis-of-oligoesters-of-hydroxy-fa https://doi.org/10.1002/biot.201700629 en eng https://edepot.wur.nl/453929 https://research.wur.nl/en/publications/biocatalytic-route-for-the-synthesis-of-oligoesters-of-hydroxy-fa doi:10.1002/biot.201700629 info:eu-repo/semantics/restrictedAccess Wageningen University & Research Biotechnology Journal 13 (2018) 6 ISSN: 1860-6768 biocatalysis biopolymers hydroxy-fatty acids lipase ϵ-caprolactone info:eu-repo/semantics/article Article/Letter to editor info:eu-repo/semantics/publishedVersion 2018 ftunivwagenin https://doi.org/10.1002/biot.201700629 2023-12-20T23:16:51Z Developments of past years placed the bio-based polyesters as competitive substitutes for fossil-based polymers. Moreover, enzymatic polymerization using lipase catalysts has become an important green alternative to chemical polymerization for the synthesis of polyesters with biomedical applications, as several drawbacks related to the presence of traces of metal catalysts, toxicity and higher temperatures could be avoided. Copolymerization of ϵ-caprolactone (CL) with four hydroxy-fatty acids (HFA) from renewable sources, 10-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid, and 16-hydroxyhexadecanoic acid, was carried out using commercially available immobilized lipases from Candida antarctica B, Thermomyces lanuginosus, and Pseudomonas stutzeri, as well as a native lipase. MALDI-TOF-MS and 2D-NMR analysis confirmed the formation of linear/branched and cyclic oligomers with average molecular weight around 1200 and polymerization degree up to 15. The appropriate selection of the biocatalyst and reaction temperature allowed the tailoring of the non-cyclic/cyclic copolymer ratio and increase of the total copolymer content in the reaction product above 80%. The catalytic efficiency of the best performing biocatalyst (Lipozyme TL) is evaluated during four reaction cycles, showing excellent operational stability. The thermal stability of the reaction products is assessed based on TG and DSC analysis. This new synthetic route for biobased oligomers with novel functionalities and properties could have promising biomedical applications. Article in Journal/Newspaper Antarc* Antarctica Wageningen UR (University & Research Centre): Digital Library Biotechnology Journal 1700629 |
institution |
Open Polar |
collection |
Wageningen UR (University & Research Centre): Digital Library |
op_collection_id |
ftunivwagenin |
language |
English |
topic |
biocatalysis biopolymers hydroxy-fatty acids lipase ϵ-caprolactone |
spellingShingle |
biocatalysis biopolymers hydroxy-fatty acids lipase ϵ-caprolactone Todea, Anamaria Aparaschivei, Diana Badea, Valentin Boeriu, Carmen G. Peter, Francisc Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone |
topic_facet |
biocatalysis biopolymers hydroxy-fatty acids lipase ϵ-caprolactone |
description |
Developments of past years placed the bio-based polyesters as competitive substitutes for fossil-based polymers. Moreover, enzymatic polymerization using lipase catalysts has become an important green alternative to chemical polymerization for the synthesis of polyesters with biomedical applications, as several drawbacks related to the presence of traces of metal catalysts, toxicity and higher temperatures could be avoided. Copolymerization of ϵ-caprolactone (CL) with four hydroxy-fatty acids (HFA) from renewable sources, 10-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid, and 16-hydroxyhexadecanoic acid, was carried out using commercially available immobilized lipases from Candida antarctica B, Thermomyces lanuginosus, and Pseudomonas stutzeri, as well as a native lipase. MALDI-TOF-MS and 2D-NMR analysis confirmed the formation of linear/branched and cyclic oligomers with average molecular weight around 1200 and polymerization degree up to 15. The appropriate selection of the biocatalyst and reaction temperature allowed the tailoring of the non-cyclic/cyclic copolymer ratio and increase of the total copolymer content in the reaction product above 80%. The catalytic efficiency of the best performing biocatalyst (Lipozyme TL) is evaluated during four reaction cycles, showing excellent operational stability. The thermal stability of the reaction products is assessed based on TG and DSC analysis. This new synthetic route for biobased oligomers with novel functionalities and properties could have promising biomedical applications. |
format |
Article in Journal/Newspaper |
author |
Todea, Anamaria Aparaschivei, Diana Badea, Valentin Boeriu, Carmen G. Peter, Francisc |
author_facet |
Todea, Anamaria Aparaschivei, Diana Badea, Valentin Boeriu, Carmen G. Peter, Francisc |
author_sort |
Todea, Anamaria |
title |
Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone |
title_short |
Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone |
title_full |
Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone |
title_fullStr |
Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone |
title_full_unstemmed |
Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone |
title_sort |
biocatalytic route for the synthesis of oligoesters of hydroxy-fatty acids and ϵ-caprolactone |
publishDate |
2018 |
url |
https://research.wur.nl/en/publications/biocatalytic-route-for-the-synthesis-of-oligoesters-of-hydroxy-fa https://doi.org/10.1002/biot.201700629 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Biotechnology Journal 13 (2018) 6 ISSN: 1860-6768 |
op_relation |
https://edepot.wur.nl/453929 https://research.wur.nl/en/publications/biocatalytic-route-for-the-synthesis-of-oligoesters-of-hydroxy-fa doi:10.1002/biot.201700629 |
op_rights |
info:eu-repo/semantics/restrictedAccess Wageningen University & Research |
op_doi |
https://doi.org/10.1002/biot.201700629 |
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Biotechnology Journal |
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1700629 |
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