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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Bibliographic Details
Published in:Catalysts
Main Authors: Ferdinando Zaccone, Valentina Venturi, Pier Paolo Giovannini, Claudio Trapella, Marco Narducci, Hugues Fournier, Anna Fantinati
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2021
Subjects:
ketone body ester
lipase
kinetic resolution
asymmetric synthesis
configuration inversion
Chemical technology
TP1-1185
Chemistry
QD1-999
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/catal11010140
https://doaj.org/article/69fa1dc1b8fb40048e3c36aeb6da9ea6
Description
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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