An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate
Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, ( R )-3-hydroxybutyl-( R )-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The ( R )-3-hydroxybutyl-( R )-3-hydroxybutyrate has been produ...
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MDPI AG
2021
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ftdoajarticles:oai:doaj.org/article:69fa1dc1b8fb40048e3c36aeb6da9ea6 2024-01-07T09:39:58+01:00 An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate Ferdinando Zaccone Valentina Venturi Pier Paolo Giovannini Claudio Trapella Marco Narducci Hugues Fournier Anna Fantinati 2021-01-01T00:00:00Z https://doi.org/10.3390/catal11010140 https://doaj.org/article/69fa1dc1b8fb40048e3c36aeb6da9ea6 EN eng MDPI AG https://www.mdpi.com/2073-4344/11/1/140 https://doaj.org/toc/2073-4344 doi:10.3390/catal11010140 2073-4344 https://doaj.org/article/69fa1dc1b8fb40048e3c36aeb6da9ea6 Catalysts, Vol 11, Iss 1, p 140 (2021) ketone body ester lipase kinetic resolution asymmetric synthesis configuration inversion Chemical technology TP1-1185 Chemistry QD1-999 article 2021 ftdoajarticles https://doi.org/10.3390/catal11010140 2023-12-10T01:44:47Z Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, ( R )-3-hydroxybutyl-( R )-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The ( R )-3-hydroxybutyl-( R )-3-hydroxybutyrate has been produced through the transesterification of racemic ethyl 3-hydroxybutyrate with ( R )-1,3-butanediol by exploiting the selectivity of Candida antarctica lipase B (CAL-B). The needed ( R )-1,3-butanediol was in turn obtained from the kinetic resolution of the racemate achieved by acetylation with vinyl acetate, also in this case, thanks to the enantioselectivity of the CAL-B used as catalyst. Finally, the stereochemical inversion of the unreacted ( S ) enantiomers of the ethyl 3-hydroxybutyate and 1,3-butanediol accomplished by known procedure allowed to increase the overall yield of the synthetic pathway by incorporating up to 70% of the starting racemic reagents into the final product. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Catalysts 11 1 140 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
ketone body ester lipase kinetic resolution asymmetric synthesis configuration inversion Chemical technology TP1-1185 Chemistry QD1-999 |
spellingShingle |
ketone body ester lipase kinetic resolution asymmetric synthesis configuration inversion Chemical technology TP1-1185 Chemistry QD1-999 Ferdinando Zaccone Valentina Venturi Pier Paolo Giovannini Claudio Trapella Marco Narducci Hugues Fournier Anna Fantinati An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate |
topic_facet |
ketone body ester lipase kinetic resolution asymmetric synthesis configuration inversion Chemical technology TP1-1185 Chemistry QD1-999 |
description |
Recent studies have highlighted the therapeutic and ergogenic potential of the ketone body ester, ( R )-3-hydroxybutyl-( R )-3-hydroxybutyrate. In the present work, the enzymatic synthesis of this biological active compound is reported. The ( R )-3-hydroxybutyl-( R )-3-hydroxybutyrate has been produced through the transesterification of racemic ethyl 3-hydroxybutyrate with ( R )-1,3-butanediol by exploiting the selectivity of Candida antarctica lipase B (CAL-B). The needed ( R )-1,3-butanediol was in turn obtained from the kinetic resolution of the racemate achieved by acetylation with vinyl acetate, also in this case, thanks to the enantioselectivity of the CAL-B used as catalyst. Finally, the stereochemical inversion of the unreacted ( S ) enantiomers of the ethyl 3-hydroxybutyate and 1,3-butanediol accomplished by known procedure allowed to increase the overall yield of the synthetic pathway by incorporating up to 70% of the starting racemic reagents into the final product. |
format |
Article in Journal/Newspaper |
author |
Ferdinando Zaccone Valentina Venturi Pier Paolo Giovannini Claudio Trapella Marco Narducci Hugues Fournier Anna Fantinati |
author_facet |
Ferdinando Zaccone Valentina Venturi Pier Paolo Giovannini Claudio Trapella Marco Narducci Hugues Fournier Anna Fantinati |
author_sort |
Ferdinando Zaccone |
title |
An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate |
title_short |
An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate |
title_full |
An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate |
title_fullStr |
An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate |
title_full_unstemmed |
An Alternative Enzymatic Route to the Ergogenic Ketone Body Ester (R) -3-Hydroxybutyl (R) -3-Hydroxybutyrate |
title_sort |
alternative enzymatic route to the ergogenic ketone body ester (r) -3-hydroxybutyl (r) -3-hydroxybutyrate |
publisher |
MDPI AG |
publishDate |
2021 |
url |
https://doi.org/10.3390/catal11010140 https://doaj.org/article/69fa1dc1b8fb40048e3c36aeb6da9ea6 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Catalysts, Vol 11, Iss 1, p 140 (2021) |
op_relation |
https://www.mdpi.com/2073-4344/11/1/140 https://doaj.org/toc/2073-4344 doi:10.3390/catal11010140 2073-4344 https://doaj.org/article/69fa1dc1b8fb40048e3c36aeb6da9ea6 |
op_doi |
https://doi.org/10.3390/catal11010140 |
container_title |
Catalysts |
container_volume |
11 |
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1 |
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140 |
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1787430297845891072 |