Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents
A series of carbonate and carbamate derivatives of natural phenols, tyrosol and hydroxytyrosol, were synthetized through a chemo-enzymatic flow approach. First, the chemoselective synthesis of tyrosol and hydroxytyrosol carbonates was performed using immobilized lipase B from Candida antarctica as c...
Published in: | Sustainable Chemistry and Pharmacy |
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Online Access: | https://hdl.handle.net/2434/1042382 https://doi.org/10.1016/j.scp.2024.101542 |
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ftunivmilanoair:oai:air.unimi.it:2434/1042382 2024-06-23T07:47:51+00:00 Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents Sara Vicinanza Lara Mombelli Francesca Annunziata Silvia Donzella Martina Letizia Contente Chiara Borsari Paola Conti Gabriele Meroni Francesco Molinari Piera Anna Martino Andrea Pinto Lucia Tamborini S. Vicinanza L. Mombelli F. Annunziata S. Donzella M.L. Contente C. Borsari P. Conti G. Meroni F. Molinari P.A.M. Martino A. Pinto L. Tamborini 2024-06 https://hdl.handle.net/2434/1042382 https://doi.org/10.1016/j.scp.2024.101542 eng eng Elsevier info:eu-repo/semantics/altIdentifier/wos/WOS:001218298900001 volume:39 firstpage:1 lastpage:8 numberofpages:8 journal:SUSTAINABLE CHEMISTRY AND PHARMACY https://hdl.handle.net/2434/1042382 doi:10.1016/j.scp.2024.101542 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85188789954 info:eu-repo/semantics/openAccess Antimicrobial agent Flow chemistry Hydroxytyrosol Immobilized lipase Lipophilization Radical scavenger Tyrosol Settore CHIM/08 - Chimica Farmaceutica info:eu-repo/semantics/article 2024 ftunivmilanoair https://doi.org/10.1016/j.scp.2024.101542 2024-06-04T14:51:55Z A series of carbonate and carbamate derivatives of natural phenols, tyrosol and hydroxytyrosol, were synthetized through a chemo-enzymatic flow approach. First, the chemoselective synthesis of tyrosol and hydroxytyrosol carbonates was performed using immobilized lipase B from Candida antarctica as catalyst in tert-amyl alcohol, a non-conventional green solvent. Then, two selected carbonates were reacted in flow with the appropriate amine to obtain the desired carbamates. All the compounds were isolated in moderate to good yields. The carbonate and carbamate derivatives showed increased lipophilicity compared to the natural parent compounds, while maintaining similar radical scavenger properties. Moreover, their antimicrobial activity against four selected bacterial strains was evaluated and they showed improved activity in comparison with tyrosol and hydroxytyrosol. Article in Journal/Newspaper Antarc* Antarctica The University of Milan: Archivio Istituzionale della Ricerca (AIR) Sustainable Chemistry and Pharmacy 39 101542 |
institution |
Open Polar |
collection |
The University of Milan: Archivio Istituzionale della Ricerca (AIR) |
op_collection_id |
ftunivmilanoair |
language |
English |
topic |
Antimicrobial agent Flow chemistry Hydroxytyrosol Immobilized lipase Lipophilization Radical scavenger Tyrosol Settore CHIM/08 - Chimica Farmaceutica |
spellingShingle |
Antimicrobial agent Flow chemistry Hydroxytyrosol Immobilized lipase Lipophilization Radical scavenger Tyrosol Settore CHIM/08 - Chimica Farmaceutica Sara Vicinanza Lara Mombelli Francesca Annunziata Silvia Donzella Martina Letizia Contente Chiara Borsari Paola Conti Gabriele Meroni Francesco Molinari Piera Anna Martino Andrea Pinto Lucia Tamborini Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
topic_facet |
Antimicrobial agent Flow chemistry Hydroxytyrosol Immobilized lipase Lipophilization Radical scavenger Tyrosol Settore CHIM/08 - Chimica Farmaceutica |
description |
A series of carbonate and carbamate derivatives of natural phenols, tyrosol and hydroxytyrosol, were synthetized through a chemo-enzymatic flow approach. First, the chemoselective synthesis of tyrosol and hydroxytyrosol carbonates was performed using immobilized lipase B from Candida antarctica as catalyst in tert-amyl alcohol, a non-conventional green solvent. Then, two selected carbonates were reacted in flow with the appropriate amine to obtain the desired carbamates. All the compounds were isolated in moderate to good yields. The carbonate and carbamate derivatives showed increased lipophilicity compared to the natural parent compounds, while maintaining similar radical scavenger properties. Moreover, their antimicrobial activity against four selected bacterial strains was evaluated and they showed improved activity in comparison with tyrosol and hydroxytyrosol. |
author2 |
S. Vicinanza L. Mombelli F. Annunziata S. Donzella M.L. Contente C. Borsari P. Conti G. Meroni F. Molinari P.A.M. Martino A. Pinto L. Tamborini |
format |
Article in Journal/Newspaper |
author |
Sara Vicinanza Lara Mombelli Francesca Annunziata Silvia Donzella Martina Letizia Contente Chiara Borsari Paola Conti Gabriele Meroni Francesco Molinari Piera Anna Martino Andrea Pinto Lucia Tamborini |
author_facet |
Sara Vicinanza Lara Mombelli Francesca Annunziata Silvia Donzella Martina Letizia Contente Chiara Borsari Paola Conti Gabriele Meroni Francesco Molinari Piera Anna Martino Andrea Pinto Lucia Tamborini |
author_sort |
Sara Vicinanza |
title |
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
title_short |
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
title_full |
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
title_fullStr |
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
title_full_unstemmed |
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
title_sort |
chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antiradical and antimicrobial agents |
publisher |
Elsevier |
publishDate |
2024 |
url |
https://hdl.handle.net/2434/1042382 https://doi.org/10.1016/j.scp.2024.101542 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/wos/WOS:001218298900001 volume:39 firstpage:1 lastpage:8 numberofpages:8 journal:SUSTAINABLE CHEMISTRY AND PHARMACY https://hdl.handle.net/2434/1042382 doi:10.1016/j.scp.2024.101542 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85188789954 |
op_rights |
info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.1016/j.scp.2024.101542 |
container_title |
Sustainable Chemistry and Pharmacy |
container_volume |
39 |
container_start_page |
101542 |
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1802638062249836544 |