Mimicking nature: synthetic nicotinamide cofactors for C═C bioreduction using enoate reductases.

Caroline E Paul, Serena Gargiulo, Diederik J Opperman, Iván Lavandera, Vicente Gotor-Fernández, Vicente Gotor, Andreas Taglieber, Isabel W C E Arends, Frank Hollmann

Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628BL Delft, The Netherlands.

Organic letters 2013 Jan 4

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A series of synthetic nicotinamide cofactors were synthesized to replace natural nicotinamide cofactors and promote enoate reductase (ER) catalyzed reactions without compromising the activity or stereoselectivity of the bioreduction process. Conversions and enantioselectivities of >99% were obtained for C═C bioreductions, and the process was successfully upscaled. Furthermore, high chemoselectivity was observed when employing these nicotinamide cofactor mimics (mNADs) with crude extracts in ER-catalyzed reactions.

Citation

Caroline E Paul, Serena Gargiulo, Diederik J Opperman, Iván Lavandera, Vicente Gotor-Fernández, Vicente Gotor, Andreas Taglieber, Isabel W C E Arends, Frank Hollmann. Mimicking nature: synthetic nicotinamide cofactors for C═C bioreduction using enoate reductases. Organic letters. 2013 Jan 4;15(1):180-3