Journal of Organic Chemistry p. 104 - 107 (1988)
Update date:2022-08-03
Topics:
Bianchi, Daniele
Cabri, Walter
Cesti, Pietro
Francalanci, Franco
Ricci, Marco
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.
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