{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T01:47:10Z","timestamp":1760233630203,"version":"build-2065373602"},"reference-count":48,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2021,1,25]],"date-time":"2021-01-25T00:00:00Z","timestamp":1611532800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Catalysts"],"abstract":"<jats:p>Lipoaminoacids (LAA) are an important group of biosurfactants, formed by a polar hydrophilic part (amino acid) and a hydrophobic tail (lipid). The gemini LAA structures allow the formation of a supramolecular complex with bioactive molecules, like DNA, which provides them with good transfection efficiency. Since lipases are naturally involved in lipid and protein metabolism, they are an alternative to the chemical production of LAA, offering an eco-friendly biosynthetic process option. This work aimed to design the production of novel cystine derived gemini through a bioconversion system using immobilized lipases. Three lipases were used: porcine pancreatic lipase (PPL); lipase from Thermomyces lanuginosus (TLL); and lipase from Rizhomucor miehei (RML). PPL was immobilized in sol-gel lenses. L-cystine dihydrochloride and dodecylamine were used as substrates for the bioreaction. The production of LAA was evaluated by thin layer chromatography (TLC), and colorimetric reaction with eosin. The identification and quantification was carried out by High Performance Liquid Chromatographer-Mass Spectrometry (HPLC-MS\/MS). The optimization of media design included co-solvent (methanol, dimethylsulfoxide), biphasic (n-hexane and 2-propanol) or solvent-free media, in order to improve the biocatalytic reaction rates and yields. Moreover, a new medium was tested where dodecylamine was melted and added to the cystine and to the biocatalyst, building a system of mainly undissolved substrates, leading to 5 mg\/mL of LAA. Most of the volume turned into foam, which indicated the production of the biosurfactant. For the first time, the gemini derived cystine lipoaminoacid was produced, identified, and quantified in both co-solvent and solvent-free media, with the lipases PPL, RML, and TLL.<\/jats:p>","DOI":"10.3390\/catal11020164","type":"journal-article","created":{"date-parts":[[2021,1,25]],"date-time":"2021-01-25T09:59:40Z","timestamp":1611568780000},"page":"164","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Design of a New Gemini Lipoaminoacid with Immobilized Lipases Based on an Eco-Friendly Biosynthetic Process"],"prefix":"10.3390","volume":"11","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7381-9672","authenticated-orcid":false,"given":"Patr\u00edcia M.","family":"Carvalho","sequence":"first","affiliation":[{"name":"Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisbon, Av. Prof. Egas Moniz, 1649-028 Lisbon, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5790-9181","authenticated-orcid":false,"given":"Rita C.","family":"Guedes","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculdade de Farm\u00e1cia, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"},{"name":"Department of Pharmaceutical Sciences and Medicines, Faculty of Pharmacy, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5016-4634","authenticated-orcid":false,"given":"Maria R.","family":"Bronze","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences and Medicines, Faculty of Pharmacy, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"},{"name":"iBET, Instituto de Biologia Experimental e Tecnol\u00f3gica, Avenida da Rep\u00fablica, Quinta-do-Marqu\u00eas, Esta\u00e7\u00e3o Agron\u00f3mica Nacional, Apartado 12, 2780-901 Oeiras, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4599-8404","authenticated-orcid":false,"given":"C\u00e9lia M. C.","family":"Faustino","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculdade de Farm\u00e1cia, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"},{"name":"Department of Pharmaceutical Sciences and Medicines, Faculty of Pharmacy, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"}]},{"given":"Maria H. L.","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa), Faculdade de Farm\u00e1cia, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"},{"name":"Department of Pharmaceutical Sciences and Medicines, Faculty of Pharmacy, Universidade Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisbon, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"360","DOI":"10.3923\/biotech.2008.360.370","article-title":"Production, Characterisation and Applications of Biosurfactants-Review","volume":"7","author":"Rahman","year":"2008","journal-title":"Biotechnology"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3379","DOI":"10.1021\/la036452h","article-title":"Interaction of Antimicrobial Arginine-Based Cationic Surfactants with Liposomes and Lipid Monolayers","volume":"20","author":"Castillo","year":"2004","journal-title":"Langmuir"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1093\/jac\/dkl024","article-title":"Biosurfactants: Potential applications in medicine","volume":"57","author":"Rodrigues","year":"2006","journal-title":"J. Antimicrob. 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