Publicação
Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions
| Resumo: | In this work, three deep eutectic mixtures (DES 1: choline chloride/urea; DES 2: choline chloride/glycerol; and DES 3: tetrabutylammonium bromide/imidazole) were investigated as mediums for the synthesis of glucose laurate and glucose acetate. Aiming to achieve a greener and more sustainable approach, the synthesis reactions were catalyzed by lipases from Aspergillus oryzae (LAO), Candida rugosa (LCR), and porcine pancreas (LPP). The hydrolytic activity of lipases against p-nitrophenyl hexanoate revealed no evidence of enzyme inactivation when DES were used as medium. Regarding the transesterification reactions, combining LAO or LCR with DES 3 resulted in the efficient production of glucose laurate (from glucose and vinyl laurate) (conversion >60 %). The best result for LPP was observed in DES 2, with 98 % of product production after 24 hours of reaction. When replacing vinyl laurate by a smaller hydrophilic substrate, vinyl acetate, a distinct behavior was observed. LCR and LPP performed better in DES 1, yielding more than 80 % of glucose acetate after 48 hours of reaction. The catalytic activity of LAO was less pronounced, reaching only nearly 40 % of product in DES 3. The results highlight the potential of combining biocatalysis with greener and environmentally-safer solvents, for the synthesis of differentiated chain-length sugar fatty acid esters (SFAE). |
|---|---|
| Autores principais: | Noro, Jennifer Martins |
| Outros Autores: | Cabo, Joana; Freitas, David S.; Roque, Catarina S.; de Castro, Mariana; Cavaco-Paulo, Artur; Silva, C. |
| Assunto: | biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| Ano: | 2023 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1864251937523761152 |
|---|---|
| author | Noro, Jennifer Martins |
| author2 | Cabo, Joana Freitas, David S. Roque, Catarina S. de Castro, Mariana Cavaco-Paulo, Artur Silva, C. |
| author2_role | author author author author author author |
| author_facet | Noro, Jennifer Martins Cabo, Joana Freitas, David S. Roque, Catarina S. de Castro, Mariana Cavaco-Paulo, Artur Silva, C. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_str | [{\"Person.name\":\"Noro, Jennifer Martins\"},{\"Person.name\":\"Cabo, Joana\"},{\"Person.name\":\"Freitas, David S.\"},{\"Person.name\":\"Roque, Catarina S.\"},{\"Person.name\":\"de Castro, Mariana\"},{\"Person.name\":\"Cavaco-Paulo, Artur\"},{\"Person.name\":\"Silva, C.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Noro, Jennifer Martins Cabo, Joana Freitas, David S. Roque, Catarina S. de Castro, Mariana Cavaco-Paulo, Artur Silva, C. |
| datacite.date.Accepted.fl_str_mv | 2023-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2024-03-25T12:28:24Z |
| datacite.date.embargoed.fl_str_mv | 2024-03-25T12:28:24Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| datacite.titles.title.fl_str_mv | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Noro, Jennifer Martins Cabo, Joana Freitas, David S. Roque, Catarina S. de Castro, Mariana Cavaco-Paulo, Artur Silva, C. |
| dc.date.Accepted.fl_str_mv | 2023-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2024-03-25T12:28:24Z |
| dc.date.embargoed.fl_str_mv | 2024-03-25T12:28:24Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/89953 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Wiley |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| dc.title.fl_str_mv | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | In this work, three deep eutectic mixtures (DES 1: choline chloride/urea; DES 2: choline chloride/glycerol; and DES 3: tetrabutylammonium bromide/imidazole) were investigated as mediums for the synthesis of glucose laurate and glucose acetate. Aiming to achieve a greener and more sustainable approach, the synthesis reactions were catalyzed by lipases from Aspergillus oryzae (LAO), Candida rugosa (LCR), and porcine pancreas (LPP). The hydrolytic activity of lipases against p-nitrophenyl hexanoate revealed no evidence of enzyme inactivation when DES were used as medium. Regarding the transesterification reactions, combining LAO or LCR with DES 3 resulted in the efficient production of glucose laurate (from glucose and vinyl laurate) (conversion >60 %). The best result for LPP was observed in DES 2, with 98 % of product production after 24 hours of reaction. When replacing vinyl laurate by a smaller hydrophilic substrate, vinyl acetate, a distinct behavior was observed. LCR and LPP performed better in DES 1, yielding more than 80 % of glucose acetate after 48 hours of reaction. The catalytic activity of LAO was less pronounced, reaching only nearly 40 % of product in DES 3. The results highlight the potential of combining biocatalysis with greener and environmentally-safer solvents, for the synthesis of differentiated chain-length sugar fatty acid esters (SFAE). |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/a510b29d-9a0a-44de-9fa2-6068b8e54e3b/download |
| id | rum_32049146741b5e182c032ef67bd9c4ac |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/89953 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/89953 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Noro, Jennifer Martins Cabo, Joana Freitas, David S. Roque, Catarina S. de Castro, Mariana Cavaco-Paulo, Artur Silva, C. |
| publishDate | 2023 |
| publisher.none.fl_str_mv | Wiley |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engWileyporIn this work, three deep eutectic mixtures (DES 1: choline chloride/urea; DES 2: choline chloride/glycerol; and DES 3: tetrabutylammonium bromide/imidazole) were investigated as mediums for the synthesis of glucose laurate and glucose acetate. Aiming to achieve a greener and more sustainable approach, the synthesis reactions were catalyzed by lipases from Aspergillus oryzae (LAO), Candida rugosa (LCR), and porcine pancreas (LPP). The hydrolytic activity of lipases against p-nitrophenyl hexanoate revealed no evidence of enzyme inactivation when DES were used as medium. Regarding the transesterification reactions, combining LAO or LCR with DES 3 resulted in the efficient production of glucose laurate (from glucose and vinyl laurate) (conversion >60 %). The best result for LPP was observed in DES 2, with 98 % of product production after 24 hours of reaction. When replacing vinyl laurate by a smaller hydrophilic substrate, vinyl acetate, a distinct behavior was observed. LCR and LPP performed better in DES 1, yielding more than 80 % of glucose acetate after 48 hours of reaction. The catalytic activity of LAO was less pronounced, reaching only nearly 40 % of product in DES 3. The results highlight the potential of combining biocatalysis with greener and environmentally-safer solvents, for the synthesis of differentiated chain-length sugar fatty acid esters (SFAE).application/pdfporDeep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactionsNoro, Jennifer MartinsCabo, JoanaFreitas, David S.Roque, Catarina S.de Castro, MarianaCavaco-Paulo, ArturSilva, C.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf1864-5631DOIIsPartOf10.1002/cssc.2023006152024-03-25T12:28:24Z20232023-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/89953http://purl.org/coar/access_right/c_abf2open accessbiocatalysisdeep eutectic solventglucose esterslipasetransesterification623828 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/a510b29d-9a0a-44de-9fa2-6068b8e54e3b/download |
| spellingShingle | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions Noro, Jennifer Martins biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| subject.fl_str_mv | biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| title | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| title_full | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| title_fullStr | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| title_full_unstemmed | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| title_short | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| title_sort | Deep eutectic solvents as suitable solvents for lipase-catalyzed transesterification reactions |
| topic | biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| topic_facet | biocatalysis deep eutectic solvent glucose esters lipase transesterification |
| url | https://hdl.handle.net/1822/89953 |
| visible | 1 |