D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties
International audience Efficient enzymatic synthesis of D-xylose and L-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalyzed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of D-xylose or L-arabinose and vinyl la...
Published in: | Enzyme and Microbial Technology |
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Online Access: | https://hal.archives-ouvertes.fr/hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676/document https://hal.archives-ouvertes.fr/hal-02962676/file/pdf-soumis.pdf https://doi.org/10.1016/j.enzmictec.2018.01.008 |
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ftunivpicardie:oai:HAL:hal-02962676v1 2023-05-15T13:58:05+02:00 D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties Méline, Thomas Muzard, Murielle Deleu, Magali Rakotoarivonina, Harivony Plantier-Royon, Richard Rémond, Caroline Université de Reims Champagne-Ardenne (URCA) Université de Liège - Gembloux 2018 https://hal.archives-ouvertes.fr/hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676/document https://hal.archives-ouvertes.fr/hal-02962676/file/pdf-soumis.pdf https://doi.org/10.1016/j.enzmictec.2018.01.008 en eng HAL CCSD Elsevier info:eu-repo/semantics/altIdentifier/doi/10.1016/j.enzmictec.2018.01.008 info:eu-repo/semantics/altIdentifier/pmid/29499775 hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676/document https://hal.archives-ouvertes.fr/hal-02962676/file/pdf-soumis.pdf doi:10.1016/j.enzmictec.2018.01.008 PRODINRA: 426562 PUBMED: 29499775 WOS: 000428099200003 info:eu-repo/semantics/OpenAccess ISSN: 0141-0229 Enzyme and Microbial Technology https://hal.archives-ouvertes.fr/hal-02962676 Enzyme and Microbial Technology, Elsevier, 2018, 112, pp.14-21. ⟨10.1016/j.enzmictec.2018.01.008⟩ Biorefinery D-Xylose laurate esters L-Arabinose laurate esters Lipase Surfactants [SDV]Life Sciences [q-bio] info:eu-repo/semantics/article Journal articles 2018 ftunivpicardie https://doi.org/10.1016/j.enzmictec.2018.01.008 2022-09-28T16:14:39Z International audience Efficient enzymatic synthesis of D-xylose and L-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalyzed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of D-xylose or L-arabinose and vinyl laurate at 50 °C. In case of L-arabinose, one monoester and one diester were obtained in a 57 % overall yield. A more complex mixture was produced for D-xylose as two monoesters and two diesters were synthesized in a 74.9 % global yield. The structures of all these pentose laurate esters was solved. Results demonstrated that the esterification first occurred regioselectively onto the primary hydroxyl groups. Pentose laurate esters exhibited interesting features such as low critical aggregation concentrations values all inferior to 25 µM. Our study demonstrates that the enzymatic production of L-arabinose and D-xylose-based esters represents an interesting approach for the production of green surfactants from lignocellulosic biomass-derived pentoses. Article in Journal/Newspaper Antarc* Antarctica Université de Picardie Jules Verne Enzyme and Microbial Technology 112 14 21 |
institution |
Open Polar |
collection |
Université de Picardie Jules Verne |
op_collection_id |
ftunivpicardie |
language |
English |
topic |
Biorefinery D-Xylose laurate esters L-Arabinose laurate esters Lipase Surfactants [SDV]Life Sciences [q-bio] |
spellingShingle |
Biorefinery D-Xylose laurate esters L-Arabinose laurate esters Lipase Surfactants [SDV]Life Sciences [q-bio] Méline, Thomas Muzard, Murielle Deleu, Magali Rakotoarivonina, Harivony Plantier-Royon, Richard Rémond, Caroline D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
topic_facet |
Biorefinery D-Xylose laurate esters L-Arabinose laurate esters Lipase Surfactants [SDV]Life Sciences [q-bio] |
description |
International audience Efficient enzymatic synthesis of D-xylose and L-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalyzed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of D-xylose or L-arabinose and vinyl laurate at 50 °C. In case of L-arabinose, one monoester and one diester were obtained in a 57 % overall yield. A more complex mixture was produced for D-xylose as two monoesters and two diesters were synthesized in a 74.9 % global yield. The structures of all these pentose laurate esters was solved. Results demonstrated that the esterification first occurred regioselectively onto the primary hydroxyl groups. Pentose laurate esters exhibited interesting features such as low critical aggregation concentrations values all inferior to 25 µM. Our study demonstrates that the enzymatic production of L-arabinose and D-xylose-based esters represents an interesting approach for the production of green surfactants from lignocellulosic biomass-derived pentoses. |
author2 |
Université de Reims Champagne-Ardenne (URCA) Université de Liège - Gembloux |
format |
Article in Journal/Newspaper |
author |
Méline, Thomas Muzard, Murielle Deleu, Magali Rakotoarivonina, Harivony Plantier-Royon, Richard Rémond, Caroline |
author_facet |
Méline, Thomas Muzard, Murielle Deleu, Magali Rakotoarivonina, Harivony Plantier-Royon, Richard Rémond, Caroline |
author_sort |
Méline, Thomas |
title |
D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
title_short |
D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
title_full |
D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
title_fullStr |
D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
title_full_unstemmed |
D-xylose and L-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
title_sort |
d-xylose and l-arabinose laurate esters : enzymatic synthesis, characterization and physico-chemical properties |
publisher |
HAL CCSD |
publishDate |
2018 |
url |
https://hal.archives-ouvertes.fr/hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676/document https://hal.archives-ouvertes.fr/hal-02962676/file/pdf-soumis.pdf https://doi.org/10.1016/j.enzmictec.2018.01.008 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
ISSN: 0141-0229 Enzyme and Microbial Technology https://hal.archives-ouvertes.fr/hal-02962676 Enzyme and Microbial Technology, Elsevier, 2018, 112, pp.14-21. ⟨10.1016/j.enzmictec.2018.01.008⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.enzmictec.2018.01.008 info:eu-repo/semantics/altIdentifier/pmid/29499775 hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676 https://hal.archives-ouvertes.fr/hal-02962676/document https://hal.archives-ouvertes.fr/hal-02962676/file/pdf-soumis.pdf doi:10.1016/j.enzmictec.2018.01.008 PRODINRA: 426562 PUBMED: 29499775 WOS: 000428099200003 |
op_rights |
info:eu-repo/semantics/OpenAccess |
op_doi |
https://doi.org/10.1016/j.enzmictec.2018.01.008 |
container_title |
Enzyme and Microbial Technology |
container_volume |
112 |
container_start_page |
14 |
op_container_end_page |
21 |
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1766266106763280384 |