Enzymatic Hydrolysis of Alkyl 3,4-Epoxybutyrates. A New Route to (R)-(-)-Carnitine Chloride

Article abstract of DOI:10.1021/jo00236a021

The enzyme-catalyzed hydrolysis of alkyl 3,4-epoxybutyrates to the corresponding epoxy acids is reported.By using esterases the reaction occurred with good stereoselectivity leading to optically active unreacted esters of R configuration.With proteases the stereoselectivity was reversed, and the S enantiomer of the unreacted ester was recovered, albeit in lover enantiomeric excess.Finally, upon preliminary optimization of the reaction conditions, a new synthesis of (R)-(-)-carnitine chloride by the successive use of a stereoselective and of a nonstereoselective enzymatic hydrolysis is shown.