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...
Published in: | Catalysts |
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Main Authors: | , , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
MDPI AG
2021
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Subjects: | |
Online Access: | https://doi.org/10.3390/catal11010140 https://doaj.org/article/69fa1dc1b8fb40048e3c36aeb6da9ea6 |
Summary: | 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. |
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