Nitrile as Activating Group in the Asymmetric Bioreduction of β‐Cyanoacrylic Acids Catalyzed by Ene‐Reductases

Abstract

Abstract Asymmetric bioreduction of an ( E )‐β‐cyano‐2,4‐dienoic acid derivative by ene‐reductases allowed a shortened access to a precursor of pregabalin [( S )‐3‐(aminomethyl)‐5‐methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% ee . Deuterium labelling studies showed that the nitrile moiety was the preferred activating/anchor group in the active site of the enzyme over the carboxylic acid or the corresponding methyl ester. magnified image