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 ketone body ester, (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate. In present work, enzymatic synthesis this biological active compound is reported. The (R)-3-hydroxybutyl-(R)-3-hydroxybutyrate has been produced through transesterification racemic ethyl 3-hydroxybutyrate with (R)-1,3-butanediol by exploiting selectivity Candida antarctica lipase B (CAL-B). needed was in turn obtained from kinetic resolution racemate achieved acetylation vinyl acetate, also case, thanks to enantioselectivity CAL-B used as catalyst. Finally, stereochemical inversion unreacted (S) enantiomers 3-hydroxybutyate 1,3-butanediol accomplished known procedure allowed increase overall yield synthetic pathway incorporating up 70% starting reagents into final product.