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

• Published in: Advanced synthesis & catalysis Vol. 356; no. 8; pp. 1878 - 1882
• Main Authors: 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
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 26.05.2014
• Subjects: Asymmetry; Chemistry; Chemistry, Applied; Chemistry, Organic; Conversion; Derivatives; Deuterium; Esters; Labelling; Nitriles; Physical Sciences; Precursors; Science & Technology; SITE; STEREOCONTROL; CC reduction; CRYSTAL-STRUCTURE; ENOATE REDUCTASES; biocatalysis; OLD YELLOW ENZYME; FAMILY; ALKENES; ESTERS; pregabalin; cyanoacrylates; ene-reductases; TOMATO; PENTAERYTHRITOL TETRANITRATE REDUCTASE

Asymmetric bioreduction of an (E)--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 t...