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


ABSTRACT: 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 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.

SUBMITTER: Winkler CK 

PROVIDER: S-EPMC4498475 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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

Winkler Christoph K CK   Clay Dorina D   Turrini Nikolaus G NG   Lechner Horst H   Kroutil Wolfgang W   Davies Simon S   Debarge Sebastien S   O'Neill Pat P   Steflik Jeremy J   Karmilowicz Mike M   Wong John W JW   Faber Kurt K  

Advanced synthesis & catalysis 20140409 8


Asymmetric bioreduction of an (<i>E</i>)-β-cyano-2,4-dienoic acid derivative by ene-reductases allowed a shortened access to a precursor of pregabalin [(<i>S</i>)-3-(aminomethyl)-5-methylhexanoic acid] possessing the desired configuration in up to 94% conversion and >99% <i>ee</i>. 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. ...[more]

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