Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent
To exploit the hydrolytic activity and high selectivity of immobilized lipase B from <i>Candida antarctica</i> on octyl agarose (CALB-OC) in the hydrolysis of triacetin and also to produce new value-added compounds from glycerol, this work describes a chemoenzymatic methodology for the s...
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MDPI AG
2020-09-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/21/18/6501 |
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| author | Esteban Plata Mónica Ruiz Jennifer Ruiz Claudia Ortiz John J. Castillo Roberto Fernández-Lafuente |
| author_facet | Esteban Plata Mónica Ruiz Jennifer Ruiz Claudia Ortiz John J. Castillo Roberto Fernández-Lafuente |
| author_sort | Esteban Plata |
| collection | DOAJ |
| description | To exploit the hydrolytic activity and high selectivity of immobilized lipase B from <i>Candida antarctica</i> on octyl agarose (CALB-OC) in the hydrolysis of triacetin and also to produce new value-added compounds from glycerol, this work describes a chemoenzymatic methodology for the synthesis of the new dimeric glycerol ester 3-((2,3-diacetoxypropanoyl)oxy)propane-1,2-diyl diacetate. According to this approach, triacetin was regioselectively hydrolyzed to 1,2-diacetin with CALB-OC. The diglyceride product was subsequently oxidized with pyridinium chlorochromate (PCC) and a dimeric ester was isolated as the only product. It was found that the medium acidity during the PCC treatment and a high 1,2-diacetin concentration favored the formation of the ester. The synthesized compounds were characterized using IR, MS, HR-MS, and NMR techniques. The obtained dimeric ester was evaluated at 100 ppm against seven bacterial strains and two <i>Candida</i> species to identify its antimicrobial activity. The compound has no inhibitory activity against the bacterial strains used but decreased <i>C. albicans</i> and <i>C. parapsilosis</i> growth by 49% and 68%, respectively. Hemolytic activity was evaluated, and the results obtained support the use of the dimeric ester to control <i>C. albicans</i> and <i>C. parapsilosis</i> growth in non-intravenous applications because the compound shows hemolytic activity. |
| first_indexed | 2024-03-10T16:33:17Z |
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| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T16:33:17Z |
| publishDate | 2020-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-d7e3530b7d15463583427076ac7006bf2023-11-20T12:42:51ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-09-012118650110.3390/ijms21186501Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing AgentEsteban Plata0Mónica Ruiz1Jennifer Ruiz2Claudia Ortiz3John J. Castillo4Roberto Fernández-Lafuente5Escuela de Química, Grupo de investigación en Bioquímica y Microbiología (GIBIM), Edificio Camilo Torres 210, Universidad Industrial de Santander, CEP, 680001 Bucaramanga, ColombiaEscuela de Química, Grupo de investigación en Bioquímica y Microbiología (GIBIM), Edificio Camilo Torres 210, Universidad Industrial de Santander, CEP, 680001 Bucaramanga, ColombiaEscuela de Química, Grupo de investigación en Bioquímica y Microbiología (GIBIM), Edificio Camilo Torres 210, Universidad Industrial de Santander, CEP, 680001 Bucaramanga, ColombiaEscuela de Microbiología, Universidad Industrial de Santander, 680001 Bucaramanga, ColombiaEscuela de Química, Grupo de investigación en Bioquímica y Microbiología (GIBIM), Edificio Camilo Torres 210, Universidad Industrial de Santander, CEP, 680001 Bucaramanga, ColombiaICP-CSIC, Campus UAM-CSIC, Cantoblanco, 28049 Madrid, SpainTo exploit the hydrolytic activity and high selectivity of immobilized lipase B from <i>Candida antarctica</i> on octyl agarose (CALB-OC) in the hydrolysis of triacetin and also to produce new value-added compounds from glycerol, this work describes a chemoenzymatic methodology for the synthesis of the new dimeric glycerol ester 3-((2,3-diacetoxypropanoyl)oxy)propane-1,2-diyl diacetate. According to this approach, triacetin was regioselectively hydrolyzed to 1,2-diacetin with CALB-OC. The diglyceride product was subsequently oxidized with pyridinium chlorochromate (PCC) and a dimeric ester was isolated as the only product. It was found that the medium acidity during the PCC treatment and a high 1,2-diacetin concentration favored the formation of the ester. The synthesized compounds were characterized using IR, MS, HR-MS, and NMR techniques. The obtained dimeric ester was evaluated at 100 ppm against seven bacterial strains and two <i>Candida</i> species to identify its antimicrobial activity. The compound has no inhibitory activity against the bacterial strains used but decreased <i>C. albicans</i> and <i>C. parapsilosis</i> growth by 49% and 68%, respectively. Hemolytic activity was evaluated, and the results obtained support the use of the dimeric ester to control <i>C. albicans</i> and <i>C. parapsilosis</i> growth in non-intravenous applications because the compound shows hemolytic activity.https://www.mdpi.com/1422-0067/21/18/6501chemoenzymatic synthesisglycerol derivativesinterfacially activated lipaseregioselective hydrolysisdiacetin oxidationpyridinium chlorochromate |
| spellingShingle | Esteban Plata Mónica Ruiz Jennifer Ruiz Claudia Ortiz John J. Castillo Roberto Fernández-Lafuente Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent International Journal of Molecular Sciences chemoenzymatic synthesis glycerol derivatives interfacially activated lipase regioselective hydrolysis diacetin oxidation pyridinium chlorochromate |
| title | Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent |
| title_full | Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent |
| title_fullStr | Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent |
| title_full_unstemmed | Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent |
| title_short | Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from <i>Candida</i> <i>antarctica</i> and Pyridinium Chlorochromate as an Oxidizing Agent |
| title_sort | chemoenzymatic synthesis of the new 3 2 3 diacetoxypropanoyl oxy propane 1 2 diyl diacetate using immobilized lipase b from i candida i i antarctica i and pyridinium chlorochromate as an oxidizing agent |
| topic | chemoenzymatic synthesis glycerol derivatives interfacially activated lipase regioselective hydrolysis diacetin oxidation pyridinium chlorochromate |
| url | https://www.mdpi.com/1422-0067/21/18/6501 |
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