Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers
Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)-NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)-have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida...
Published in: | Frontiers in Chemistry |
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ftccsdartic:oai:HAL:hal-01727154v1 2023-05-15T13:31:37+02:00 Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers Diot-Néant, Florian Migeot, Loïs Hollande, Louis Reano, Felix A. Domenek, Sandra ALLAIS, Florent Agro-Biotechnologies Industrielles (ABI) AgroParisTech University of Florida Gainesville (UF) Ingénierie, Procédés, Aliments (GENIAL) Institut National de la Recherche Agronomique (INRA)-AgroParisTech Université Paris-Saclay Génie et Microbiologie des Procédés Alimentaires (GMPA) Région Grand Est Conseil Départemental de la Marne Grand Reims 2017 https://hal.archives-ouvertes.fr/hal-01727154 https://hal.archives-ouvertes.fr/hal-01727154/document https://hal.archives-ouvertes.fr/hal-01727154/file/2017_Diot-N%C3%A9ant_Frontiers%20in%20Chemistry.pdf https://doi.org/10.3389/fchem.2017.00126 en eng HAL CCSD Frontiers Media info:eu-repo/semantics/altIdentifier/pmid/29312930 info:eu-repo/semantics/altIdentifier/doi/10.3389/fchem.2017.00126 hal-01727154 https://hal.archives-ouvertes.fr/hal-01727154 https://hal.archives-ouvertes.fr/hal-01727154/document https://hal.archives-ouvertes.fr/hal-01727154/file/2017_Diot-N%C3%A9ant_Frontiers%20in%20Chemistry.pdf PRODINRA: 423110 PUBMED: 29312930 doi:10.3389/fchem.2017.00126 WOS: 000418588800002 http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess EISSN: 2296-2646 Frontiers in Chemistry https://hal.archives-ouvertes.fr/hal-01727154 Frontiers in Chemistry, Frontiers Media, 2017, 5, pp.1-10. ⟨10.3389/fchem.2017.00126⟩ https://www.frontiersin.org/journals/chemistry sinapic acid DPPH antioxidants ROMP lipase CAL-B norbornene ferulic acid [CHIM.POLY]Chemical Sciences/Polymers info:eu-repo/semantics/article Journal articles 2017 ftccsdartic https://doi.org/10.3389/fchem.2017.00126 2021-12-19T02:24:12Z Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)-NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)-have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida antarctica Lipase B (Cal-B). The ring opening metathesis polymerization (ROMP) of these monomers was investigated according to ruthenium catalyst type (GI) vs. (HGII) and monomer to catalyst molar ratio ([M]/[C]). The co-polymerization of antioxidant functionalized monomer (NDF or NDS) and non-active norbornene (N) has also been performed in order to adjust the number of SHP groups present per weight unit and tune the antioxidant activity of the copolymers. The polydispersity of the resulting copolymers was readily improved by a simple acetone wash to provide antioxidant polymers with well-defined structures. After hydrogenation with p-toluenesulfonylhydrazine (p-TSH), the radical scavenging ability of the resulting saturated polymers was evaluated using α,α-diphenyl-β-picrylhydrazyl (DPPH) analysis. Results demonstrated that polymers bearing sinapic acid SHP exhibited higher antiradical activity than the polymer bearing ferulic acid SHP. In addition it was also shown that only a small SHP content was needed in the copolymers to exhibit a potent antioxidant activity. Article in Journal/Newspaper Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) Frontiers in Chemistry 5 |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
English |
topic |
sinapic acid DPPH antioxidants ROMP lipase CAL-B norbornene ferulic acid [CHIM.POLY]Chemical Sciences/Polymers |
spellingShingle |
sinapic acid DPPH antioxidants ROMP lipase CAL-B norbornene ferulic acid [CHIM.POLY]Chemical Sciences/Polymers Diot-Néant, Florian Migeot, Loïs Hollande, Louis Reano, Felix A. Domenek, Sandra ALLAIS, Florent Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
topic_facet |
sinapic acid DPPH antioxidants ROMP lipase CAL-B norbornene ferulic acid [CHIM.POLY]Chemical Sciences/Polymers |
description |
Antioxidant norbornene-based monomers bearing biobased sterically hindered phenols (SHP)-NDF (norbornene dihydroferulate) and NDS (norbornene dihydrosinapate)-have been successfully prepared through biocatalysis from naturally occurring ferulic and sinapic acids, respectively, in presence of Candida antarctica Lipase B (Cal-B). The ring opening metathesis polymerization (ROMP) of these monomers was investigated according to ruthenium catalyst type (GI) vs. (HGII) and monomer to catalyst molar ratio ([M]/[C]). The co-polymerization of antioxidant functionalized monomer (NDF or NDS) and non-active norbornene (N) has also been performed in order to adjust the number of SHP groups present per weight unit and tune the antioxidant activity of the copolymers. The polydispersity of the resulting copolymers was readily improved by a simple acetone wash to provide antioxidant polymers with well-defined structures. After hydrogenation with p-toluenesulfonylhydrazine (p-TSH), the radical scavenging ability of the resulting saturated polymers was evaluated using α,α-diphenyl-β-picrylhydrazyl (DPPH) analysis. Results demonstrated that polymers bearing sinapic acid SHP exhibited higher antiradical activity than the polymer bearing ferulic acid SHP. In addition it was also shown that only a small SHP content was needed in the copolymers to exhibit a potent antioxidant activity. |
author2 |
Agro-Biotechnologies Industrielles (ABI) AgroParisTech University of Florida Gainesville (UF) Ingénierie, Procédés, Aliments (GENIAL) Institut National de la Recherche Agronomique (INRA)-AgroParisTech Université Paris-Saclay Génie et Microbiologie des Procédés Alimentaires (GMPA) Région Grand Est Conseil Départemental de la Marne Grand Reims |
format |
Article in Journal/Newspaper |
author |
Diot-Néant, Florian Migeot, Loïs Hollande, Louis Reano, Felix A. Domenek, Sandra ALLAIS, Florent |
author_facet |
Diot-Néant, Florian Migeot, Loïs Hollande, Louis Reano, Felix A. Domenek, Sandra ALLAIS, Florent |
author_sort |
Diot-Néant, Florian |
title |
Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
title_short |
Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
title_full |
Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
title_fullStr |
Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
title_full_unstemmed |
Biocatalytic synthesis and polymerization via ROMP of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
title_sort |
biocatalytic synthesis and polymerization via romp of new biobased phenolic monomers: a greener process toward sustainable antioxidant polymers |
publisher |
HAL CCSD |
publishDate |
2017 |
url |
https://hal.archives-ouvertes.fr/hal-01727154 https://hal.archives-ouvertes.fr/hal-01727154/document https://hal.archives-ouvertes.fr/hal-01727154/file/2017_Diot-N%C3%A9ant_Frontiers%20in%20Chemistry.pdf https://doi.org/10.3389/fchem.2017.00126 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
EISSN: 2296-2646 Frontiers in Chemistry https://hal.archives-ouvertes.fr/hal-01727154 Frontiers in Chemistry, Frontiers Media, 2017, 5, pp.1-10. ⟨10.3389/fchem.2017.00126⟩ https://www.frontiersin.org/journals/chemistry |
op_relation |
info:eu-repo/semantics/altIdentifier/pmid/29312930 info:eu-repo/semantics/altIdentifier/doi/10.3389/fchem.2017.00126 hal-01727154 https://hal.archives-ouvertes.fr/hal-01727154 https://hal.archives-ouvertes.fr/hal-01727154/document https://hal.archives-ouvertes.fr/hal-01727154/file/2017_Diot-N%C3%A9ant_Frontiers%20in%20Chemistry.pdf PRODINRA: 423110 PUBMED: 29312930 doi:10.3389/fchem.2017.00126 WOS: 000418588800002 |
op_rights |
http://creativecommons.org/licenses/by/ info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.3389/fchem.2017.00126 |
container_title |
Frontiers in Chemistry |
container_volume |
5 |
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1766019346713280512 |