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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 (\u22126.5 kcal\u00b7mol\u22121) than with tripalmitin (5.4 kcal\u00b7mol\u22121). 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\u201372 \u00b0C) and oleic acid\/tripalmitin molar ratio (MR = 2:1\u20136.8:1), was performed for acidolysis optimization. Under optimized conditions (58 \u00b0C and MR = 4:1 or 60 \u00b0C and MR = 2:1), the oleic acid incorporation of 28 mol.% was achieved after 48 h.<\/jats:p>","DOI":"10.3390\/catal13050825","type":"journal-article","created":{"date-parts":[[2023,5,1]],"date-time":"2023-05-01T13:54:46Z","timestamp":1682949286000},"page":"825","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Production of Human Milk Fat Substitutes by Lipase-Catalyzed Acidolysis: Immobilization, Synthesis, Molecular Docking and Optimization Studies"],"prefix":"10.3390","volume":"13","author":[{"given":"Cleide M. F.","family":"Soares","sequence":"first","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Engenharia de Processos, UNIT\u2014Universidade Tiradentes, Av. Murilo Dantas, 300, Farol\u00e2ndia, Aracaju 49032-490, SE, Brazil"},{"name":"ITP\u2014Instituto de Tecnologia e Pesquisa, Av. Murilo Dantas, 300, Pr\u00e9dio do ITP, Farol\u00e2ndia, Aracaju 49032-490, SE, Brazil"}]},{"given":"Milson S.","family":"Barbosa","sequence":"additional","affiliation":[{"name":"IFPB\u2014Instituto Federal de Educa\u00e7\u00e3o, Ci\u00eancia e Tecnologia da Para\u00edba, Campus Cajazeiras, Rua Jos\u00e9 Le\u00f4ncio da Silva, 300, Jardim Oasis, Cajazeiras 58900-000, PB, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6420-406X","authenticated-orcid":false,"given":"Samuel B.","family":"Santos","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Engenharia de Processos, UNIT\u2014Universidade Tiradentes, Av. Murilo Dantas, 300, Farol\u00e2ndia, Aracaju 49032-490, SE, Brazil"}]},{"given":"Silvana","family":"Mattedi","sequence":"additional","affiliation":[{"name":"UFBA\u2014Departamento de Engenharia Qu\u00edmica, Universidade Federal da Bahia, Rua Aristides Novis 2, Federa\u00e7\u00e3o, Salvador 40210-630, BA, Brazil"}]},{"given":"\u00c1lvaro S.","family":"Lima","sequence":"additional","affiliation":[{"name":"Programa de P\u00f3s-Gradua\u00e7\u00e3o em Engenharia de Processos, UNIT\u2014Universidade Tiradentes, Av. Murilo Dantas, 300, Farol\u00e2ndia, Aracaju 49032-490, SE, Brazil"},{"name":"ITP\u2014Instituto de Tecnologia e Pesquisa, Av. Murilo Dantas, 300, Pr\u00e9dio do ITP, Farol\u00e2ndia, Aracaju 49032-490, SE, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3524-6900","authenticated-orcid":false,"given":"Matheus M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"CIEPQPF\u2014Department of Chemical Engineering, University of Coimbra, Rua S\u00edlvio Lima, P\u00f3lo II\u2014Pinhal de Marrocos, 3030-790 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2423-0495","authenticated-orcid":false,"given":"Carla","family":"Tecel\u00e3o","sequence":"additional","affiliation":[{"name":"MARE\u2014Marine and Environmental Sciences Centre, ARNET\u2014Aquatic Research Network, ESTM, Polit\u00e9cnico de Leiria, 2520-630 Peniche, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3655-8201","authenticated-orcid":false,"given":"Suzana","family":"Ferreira-Dias","sequence":"additional","affiliation":[{"name":"LEAF\u2014Linking Landscape, Environment, Agriculture and Food, Associated Laboratory TERRA, Laborat\u00f3rio de Estudos T\u00e9cnicos, Instituto Superior de Agronomia, Universidade de Lisboa, Tapada da Ajuda, 1349-017 Lisbon, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,4,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1016\/j.lwt.2014.09.013","article-title":"Synthesis of Structured Lipid 1,3-Dioleoyl-2-Palmitoylglycerol in Both Solvent and Solvent-Free System","volume":"12","author":"Wei","year":"2015","journal-title":"LWT-Food Sci. 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