Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent
To exploit the hydrolytic activity and high selectivity of immobilized lipase B from Candida antarctica 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...
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ftmdpi:oai:mdpi.com:/1422-0067/21/18/6501/ 2023-08-20T04:00:55+02:00 Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent Esteban Plata Mónica Ruiz Jennifer Ruiz Claudia Ortiz John J. Castillo Roberto Fernández-Lafuente agris 2020-09-05 application/pdf https://doi.org/10.3390/ijms21186501 EN eng Multidisciplinary Digital Publishing Institute Biochemistry https://dx.doi.org/10.3390/ijms21186501 https://creativecommons.org/licenses/by/4.0/ International Journal of Molecular Sciences; Volume 21; Issue 18; Pages: 6501 chemoenzymatic synthesis glycerol derivatives interfacially activated lipase regioselective hydrolysis diacetin oxidation pyridinium chlorochromate antibacterial activity antifungal activity hemolytic activity Text 2020 ftmdpi https://doi.org/10.3390/ijms21186501 2023-08-01T00:03:05Z To exploit the hydrolytic activity and high selectivity of immobilized lipase B from Candida antarctica 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 Candida species to identify its antimicrobial activity. The compound has no inhibitory activity against the bacterial strains used but decreased C. albicans and C. parapsilosis growth by 49% and 68%, respectively. Hemolytic activity was evaluated, and the results obtained support the use of the dimeric ester to control C. albicans and C. parapsilosis growth in non-intravenous applications because the compound shows hemolytic activity. Text Antarc* Antarctica MDPI Open Access Publishing International Journal of Molecular Sciences 21 18 6501 |
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Open Polar |
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MDPI Open Access Publishing |
op_collection_id |
ftmdpi |
language |
English |
topic |
chemoenzymatic synthesis glycerol derivatives interfacially activated lipase regioselective hydrolysis diacetin oxidation pyridinium chlorochromate antibacterial activity antifungal activity hemolytic activity |
spellingShingle |
chemoenzymatic synthesis glycerol derivatives interfacially activated lipase regioselective hydrolysis diacetin oxidation pyridinium chlorochromate antibacterial activity antifungal activity hemolytic activity 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 Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent |
topic_facet |
chemoenzymatic synthesis glycerol derivatives interfacially activated lipase regioselective hydrolysis diacetin oxidation pyridinium chlorochromate antibacterial activity antifungal activity hemolytic activity |
description |
To exploit the hydrolytic activity and high selectivity of immobilized lipase B from Candida antarctica 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 Candida species to identify its antimicrobial activity. The compound has no inhibitory activity against the bacterial strains used but decreased C. albicans and C. parapsilosis growth by 49% and 68%, respectively. Hemolytic activity was evaluated, and the results obtained support the use of the dimeric ester to control C. albicans and C. parapsilosis growth in non-intravenous applications because the compound shows hemolytic activity. |
format |
Text |
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 |
title |
Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica 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 Candida antarctica 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 Candida antarctica 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 Candida antarctica 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 Candida antarctica 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 candida antarctica and pyridinium chlorochromate as an oxidizing agent |
publisher |
Multidisciplinary Digital Publishing Institute |
publishDate |
2020 |
url |
https://doi.org/10.3390/ijms21186501 |
op_coverage |
agris |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
International Journal of Molecular Sciences; Volume 21; Issue 18; Pages: 6501 |
op_relation |
Biochemistry https://dx.doi.org/10.3390/ijms21186501 |
op_rights |
https://creativecommons.org/licenses/by/4.0/ |
op_doi |
https://doi.org/10.3390/ijms21186501 |
container_title |
International Journal of Molecular Sciences |
container_volume |
21 |
container_issue |
18 |
container_start_page |
6501 |
_version_ |
1774721221433229312 |