Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties
International audience The study of CO2-expanded liquids using a green component such as a bio-based solvent has been recently raised as a new concept for an alternative solvent, and yet been largely unexplored in literature for neither fundamental nor application studies. On the other hand, structu...
Published in: | ACS Sustainable Chemistry & Engineering |
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Online Access: | https://hal.archives-ouvertes.fr/hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311/document https://hal.archives-ouvertes.fr/hal-01630311/file/Hoang_18596.pdf https://doi.org/10.1021/acssuschemeng.7b03018 |
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ftccsdartic:oai:HAL:hal-01630311v1 2023-05-15T13:32:58+02:00 Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties Hoang, Hai Nam Granero-Fernandez, Emanuel Yamada, Shinjiro Mori, Shuichi Kagechika, Hiroyuki Medina-Gonzalez, Yaocihuatl Matsuda, Tomoko Tokyo Institute of Technology Tokyo (TITECH) Laboratoire de génie chimique ancien site de Basso-Cambo (LGC) Université Toulouse III - Paul Sabatier (UT3) Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP) Université Fédérale Toulouse Midi-Pyrénées Institute of Biomaterials and Bioengineering (IBB) Tokyo Medical and Dental University 2017 https://hal.archives-ouvertes.fr/hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311/document https://hal.archives-ouvertes.fr/hal-01630311/file/Hoang_18596.pdf https://doi.org/10.1021/acssuschemeng.7b03018 en eng HAL CCSD American Chemical Society info:eu-repo/semantics/altIdentifier/doi/10.1021/acssuschemeng.7b03018 hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311/document https://hal.archives-ouvertes.fr/hal-01630311/file/Hoang_18596.pdf OATAO: 18596 doi:10.1021/acssuschemeng.7b03018 info:eu-repo/semantics/OpenAccess ISSN: 2168-0485 ACS Sustainable Chemistry & Engineering https://hal.archives-ouvertes.fr/hal-01630311 ACS Sustainable Chemistry & Engineering, American Chemical Society, 2017, 5 (11), pp.11051-11059. ⟨10.1021/acssuschemeng.7b03018⟩ 2-Methyltetrahydrofuran Transesterification Candida antarctica lipase B Pressurized carbon dioxide Kinetic resolution Solvatochromism Green solvent engineering Substrate specificity [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry Molecular Biology/Biochemistry [q-bio.BM] [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering info:eu-repo/semantics/article Journal articles 2017 ftccsdartic https://doi.org/10.1021/acssuschemeng.7b03018 2021-11-07T03:34:45Z International audience The study of CO2-expanded liquids using a green component such as a bio-based solvent has been recently raised as a new concept for an alternative solvent, and yet been largely unexplored in literature for neither fundamental nor application studies. On the other hand, structural bulkiness of substrates remains one of the main limitations to promote enzymes as an efficient versatile catalytic tool for organic synthesis, especially biocatalysis in non-conventional solvents. Herein, we report a detailed investigation of CO2-expanded bio-based liquids as reaction media for improved biocatalysis of sterically hindered compounds. We have found that CO2 acts as a crucial trigger for various lipases to catalyse transesterification of challenging bulky alcohols in CO2-expanded 2-methyltetrahydrofuran (MeTHF). Furthermore, this study determines physicochemical and transport properties of CO2-expanded MeTHF for the first time, which were then utilized for modulating biocatalytic activity. It was found that lipase activity increased with the accordingly decrease of the dipolarity of CO2-expanded MeTHF, which is tunable by altering the concentration of CO2 in the solvent system. Article in Journal/Newspaper Antarc* Antarctica Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) ACS Sustainable Chemistry & Engineering 5 11 11051 11059 |
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 |
2-Methyltetrahydrofuran Transesterification Candida antarctica lipase B Pressurized carbon dioxide Kinetic resolution Solvatochromism Green solvent engineering Substrate specificity [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry Molecular Biology/Biochemistry [q-bio.BM] [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering |
spellingShingle |
2-Methyltetrahydrofuran Transesterification Candida antarctica lipase B Pressurized carbon dioxide Kinetic resolution Solvatochromism Green solvent engineering Substrate specificity [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry Molecular Biology/Biochemistry [q-bio.BM] [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering Hoang, Hai Nam Granero-Fernandez, Emanuel Yamada, Shinjiro Mori, Shuichi Kagechika, Hiroyuki Medina-Gonzalez, Yaocihuatl Matsuda, Tomoko Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties |
topic_facet |
2-Methyltetrahydrofuran Transesterification Candida antarctica lipase B Pressurized carbon dioxide Kinetic resolution Solvatochromism Green solvent engineering Substrate specificity [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry Molecular Biology/Biochemistry [q-bio.BM] [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering |
description |
International audience The study of CO2-expanded liquids using a green component such as a bio-based solvent has been recently raised as a new concept for an alternative solvent, and yet been largely unexplored in literature for neither fundamental nor application studies. On the other hand, structural bulkiness of substrates remains one of the main limitations to promote enzymes as an efficient versatile catalytic tool for organic synthesis, especially biocatalysis in non-conventional solvents. Herein, we report a detailed investigation of CO2-expanded bio-based liquids as reaction media for improved biocatalysis of sterically hindered compounds. We have found that CO2 acts as a crucial trigger for various lipases to catalyse transesterification of challenging bulky alcohols in CO2-expanded 2-methyltetrahydrofuran (MeTHF). Furthermore, this study determines physicochemical and transport properties of CO2-expanded MeTHF for the first time, which were then utilized for modulating biocatalytic activity. It was found that lipase activity increased with the accordingly decrease of the dipolarity of CO2-expanded MeTHF, which is tunable by altering the concentration of CO2 in the solvent system. |
author2 |
Tokyo Institute of Technology Tokyo (TITECH) Laboratoire de génie chimique ancien site de Basso-Cambo (LGC) Université Toulouse III - Paul Sabatier (UT3) Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP) Université Fédérale Toulouse Midi-Pyrénées Institute of Biomaterials and Bioengineering (IBB) Tokyo Medical and Dental University |
format |
Article in Journal/Newspaper |
author |
Hoang, Hai Nam Granero-Fernandez, Emanuel Yamada, Shinjiro Mori, Shuichi Kagechika, Hiroyuki Medina-Gonzalez, Yaocihuatl Matsuda, Tomoko |
author_facet |
Hoang, Hai Nam Granero-Fernandez, Emanuel Yamada, Shinjiro Mori, Shuichi Kagechika, Hiroyuki Medina-Gonzalez, Yaocihuatl Matsuda, Tomoko |
author_sort |
Hoang, Hai Nam |
title |
Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties |
title_short |
Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties |
title_full |
Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties |
title_fullStr |
Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties |
title_full_unstemmed |
Modulating biocatalytic activity towards sterically bulky substrates in CO2-expanded bio-based liquids by tuning physicochemical properties |
title_sort |
modulating biocatalytic activity towards sterically bulky substrates in co2-expanded bio-based liquids by tuning physicochemical properties |
publisher |
HAL CCSD |
publishDate |
2017 |
url |
https://hal.archives-ouvertes.fr/hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311/document https://hal.archives-ouvertes.fr/hal-01630311/file/Hoang_18596.pdf https://doi.org/10.1021/acssuschemeng.7b03018 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 2168-0485 ACS Sustainable Chemistry & Engineering https://hal.archives-ouvertes.fr/hal-01630311 ACS Sustainable Chemistry & Engineering, American Chemical Society, 2017, 5 (11), pp.11051-11059. ⟨10.1021/acssuschemeng.7b03018⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1021/acssuschemeng.7b03018 hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311 https://hal.archives-ouvertes.fr/hal-01630311/document https://hal.archives-ouvertes.fr/hal-01630311/file/Hoang_18596.pdf OATAO: 18596 doi:10.1021/acssuschemeng.7b03018 |
op_rights |
info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.1021/acssuschemeng.7b03018 |
container_title |
ACS Sustainable Chemistry & Engineering |
container_volume |
5 |
container_issue |
11 |
container_start_page |
11051 |
op_container_end_page |
11059 |
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1766037273284968448 |