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Production of human milk fat substitutes by lipase-catalyzed acidolysis: immobilization, synthesis, molecular docking and optimization studies

2023-05Artigo científico Acesso aberto
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dc.contributor.authorSoares, Cleide M. F.
dc.contributor.authorBarbosa, Milson S.
dc.contributor.authorSantos, Samuel B.
dc.contributor.authorMattedi, Silvana
dc.contributor.authorLima, Álvaro S.
dc.contributor.authorPereira, Matheus M.
dc.contributor.authorTecelão, Carla
dc.contributor.authorFerreira-Dias, Suzana
dc.date.accessioned2024-03-19T16:36:12Z
dc.date.available2024-03-19T16:36:12Z
dc.date.issued2023-05
dc.description.abstractHuman milk fat (HMF) triacylglycerols (TAGs) mainly contain palmitic acid esterified at the sn-2 position while oleic and other unsaturated fatty acids are located at positions sn-1,3. This study aimed at the production of HMF substitutes (HMFS) by lipase-catalyzed acidolysis of tripalmitin with oleic acid, in a solvent-free medium. Burkholderia cepacia lipase (BCL) was immobilized in silica (prepared with protic or aprotic ionic liquids) by covalent binding or encapsulation and used as biocatalyst. The supports and immobilized biocatalysts were characterized by FTIR, TGA, and SEM. Molecular docking analysis showed that BCL preferentially attacks oleic acid rather than tripalmitin, due to the lower free energy of hydrophobic binding with this acid (􀀀6.5 kcal mol􀀀1) than with tripalmitin (5.4 kcal mol􀀀1). Therefore, the tripalmitin attack by BCL and subsequent HMFS production only occurs after the binding to most of the oleic acid molecules. The highest acidolysis activity was obtained with BCL immobilized by covalent binding in prepared silica with aprotic ionic liquid. A central composite rotatable design, as a function of temperature (58–72 C) and oleic acid/tripalmitin molar ratio (MR = 2:1–6.8:1), was performed for acidolysis optimization. Under optimized conditions (58 C and MR = 4:1 or 60 C and MR = 2:1), the oleic acid incorporation of 28 mol.% was achieved after 48 h.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.3390/catal13050825pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.5/30451
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationUIDB/EQU/00102/2020pt_PT
dc.relationLinking Landscape, Environment, Agriculture and Food
dc.relationLinking Landscape, Environment, Agriculture and Food
dc.relationMarine and Environmental Sciences Centre
dc.relationMarine and Environmental Sciences Centre
dc.relationAquatic Research Infrastructure Network
dc.relation.publisherversionhttps://www.mdpi.com/journal/catalystspt_PT
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/pt_PT
dc.subjecthuman milk fat substitutespt_PT
dc.subjectimmobilizationpt_PT
dc.subjectionic liquidpt_PT
dc.subjectlipasept_PT
dc.subjectmolecular dockingpt_PT
dc.titleProduction of human milk fat substitutes by lipase-catalyzed acidolysis: immobilization, synthesis, molecular docking and optimization studiespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleLinking Landscape, Environment, Agriculture and Food
oaire.awardTitleLinking Landscape, Environment, Agriculture and Food
oaire.awardTitleMarine and Environmental Sciences Centre
oaire.awardTitleMarine and Environmental Sciences Centre
oaire.awardTitleAquatic Research Infrastructure Network
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04129%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04129%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04292%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04292%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0069%2F2020/PT
oaire.citation.issue5pt_PT
oaire.citation.startPageArticle number 825pt_PT
oaire.citation.titleCatalystspt_PT
oaire.citation.volume13pt_PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
person.familyNameFerreira-Dias
person.givenNameSuzana
person.identifier.ciencia-idAA14-7B2F-5098
person.identifier.orcid0000-0003-3655-8201
person.identifier.ridE-1128-2013
person.identifier.scopus-author-id6603615381
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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