Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor
Herein we present the biocatalysed preparation of a mono- N -carbamate-protected precursor of antitumoral Nutlin-3a through enantioselective alkoxycarbonylation of meso -1,2-disubstituted-1,2-diaminoethane using enzyme lipases and dialkyl carbonates as acylating agents. A series of supported or free...
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2024
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ftdoajarticles:oai:doaj.org/article:59b0a2d3578d4571872fd539124d04e7 2024-09-15T17:48:18+00:00 Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor Virginia Cristofori Davide Illuminati Chiara Bisquoli Martina Catani Greta Compagnin Giulia Turrin Claudio Trapella Anna Fantinati 2024-07-01T00:00:00Z https://doi.org/10.3390/molecules29143267 https://doaj.org/article/59b0a2d3578d4571872fd539124d04e7 EN eng MDPI AG https://www.mdpi.com/1420-3049/29/14/3267 https://doaj.org/toc/1420-3049 doi:10.3390/molecules29143267 1420-3049 https://doaj.org/article/59b0a2d3578d4571872fd539124d04e7 Molecules, Vol 29, Iss 14, p 3267 (2024) biocatalysis Nutlin-3a desymmetrisation vicinal meso -diamines Organic chemistry QD241-441 article 2024 ftdoajarticles https://doi.org/10.3390/molecules29143267 2024-08-05T17:48:50Z Herein we present the biocatalysed preparation of a mono- N -carbamate-protected precursor of antitumoral Nutlin-3a through enantioselective alkoxycarbonylation of meso -1,2-disubstituted-1,2-diaminoethane using enzyme lipases and dialkyl carbonates as acylating agents. A series of supported or free lipase enzymes were screened in combination with commercially available diallyl, diethyl and dimethyl carbonates. The reactions were conducted at different temperatures, for different reaction times and with variable co-solvent systems to evaluate the effects on the enzyme catalytic activity. The best results in terms of conversion, enantiomeric excess and yield were obtained when lipase from Candida antarctica B (CAL-B) was used with diallyl carbonate (DAC) when conducting the reaction solventless at 75 °C. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Molecules 29 14 3267 |
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Open Polar |
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Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
biocatalysis Nutlin-3a desymmetrisation vicinal meso -diamines Organic chemistry QD241-441 |
spellingShingle |
biocatalysis Nutlin-3a desymmetrisation vicinal meso -diamines Organic chemistry QD241-441 Virginia Cristofori Davide Illuminati Chiara Bisquoli Martina Catani Greta Compagnin Giulia Turrin Claudio Trapella Anna Fantinati Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor |
topic_facet |
biocatalysis Nutlin-3a desymmetrisation vicinal meso -diamines Organic chemistry QD241-441 |
description |
Herein we present the biocatalysed preparation of a mono- N -carbamate-protected precursor of antitumoral Nutlin-3a through enantioselective alkoxycarbonylation of meso -1,2-disubstituted-1,2-diaminoethane using enzyme lipases and dialkyl carbonates as acylating agents. A series of supported or free lipase enzymes were screened in combination with commercially available diallyl, diethyl and dimethyl carbonates. The reactions were conducted at different temperatures, for different reaction times and with variable co-solvent systems to evaluate the effects on the enzyme catalytic activity. The best results in terms of conversion, enantiomeric excess and yield were obtained when lipase from Candida antarctica B (CAL-B) was used with diallyl carbonate (DAC) when conducting the reaction solventless at 75 °C. |
format |
Article in Journal/Newspaper |
author |
Virginia Cristofori Davide Illuminati Chiara Bisquoli Martina Catani Greta Compagnin Giulia Turrin Claudio Trapella Anna Fantinati |
author_facet |
Virginia Cristofori Davide Illuminati Chiara Bisquoli Martina Catani Greta Compagnin Giulia Turrin Claudio Trapella Anna Fantinati |
author_sort |
Virginia Cristofori |
title |
Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor |
title_short |
Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor |
title_full |
Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor |
title_fullStr |
Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor |
title_full_unstemmed |
Enzymatic Desymmetrisation of Prochiral meso -1,2-Disubstituted-1,2-Diaminoethane for the Synthesis of Key Enantioenriched (−)-Nutlin-3 Precursor |
title_sort |
enzymatic desymmetrisation of prochiral meso -1,2-disubstituted-1,2-diaminoethane for the synthesis of key enantioenriched (−)-nutlin-3 precursor |
publisher |
MDPI AG |
publishDate |
2024 |
url |
https://doi.org/10.3390/molecules29143267 https://doaj.org/article/59b0a2d3578d4571872fd539124d04e7 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Molecules, Vol 29, Iss 14, p 3267 (2024) |
op_relation |
https://www.mdpi.com/1420-3049/29/14/3267 https://doaj.org/toc/1420-3049 doi:10.3390/molecules29143267 1420-3049 https://doaj.org/article/59b0a2d3578d4571872fd539124d04e7 |
op_doi |
https://doi.org/10.3390/molecules29143267 |
container_title |
Molecules |
container_volume |
29 |
container_issue |
14 |
container_start_page |
3267 |
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1810289454851555328 |