Nitrile as Activating Group in the Asymmetric Bioreduction of β??Cyanoacrylic Acids Catalyzed by Ene??Reductases
…, S Davies, S Debarge, P O'Neill, J Steflik…
Index: Winkler, Christoph K.; Clay, Dorina; Turrini, Nikolaus G.; Lechner, Horst; Kroutil, Wolfgang; Davies, Simon; Debarge, Sebastien; O'Neill, Pat; Steflik, Jeremy; Karmilowicz, Mike; Wong, John W.; Faber, Kurt Advanced Synthesis and Catalysis, 2014 , vol. 356, # 8 p. 1878 - 1882
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Citation Number: 7
Abstract
Abstract: Asymmetric bioreduction of an (E)-bcyano-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 ...
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