Breaking the Nicotinamide Habit

  • ChemPubSoc Europe Logo
  • Author: Lois O'Leary
  • Published Date: 15 February 2012
  • Source / Publisher: ChemCatChem/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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A chemoenzymatic reduction of conjugated C=C double bonds has been developed by Diederik J. Opperman, Frank Hollmann and co-workers, University of the Free State, South Africa, and Delft University of Technology, The Netherlands, respectively.

Chiral carbonyl compounds can be prepared by the enoate reductase (ER)-catalyzed asymmetric reduction of conjugated C=C double bonds. Conventional processes use the expensive nicotinamide cofactor [NAD(P)H] to regenerate the primary reductant, which necessitates an additional recycling strategy to ensure cost-effective use of the cofactor.

Based on the fact that the nicotinamide does not play a direct role in the catalytic mechanism, the group have developed NAD(P)-independent regeneration of ERs by using the rhodium catalyst [Cp*Rh(bpy)(H2O)]2+. This catalyst, with good activity and stability at high temperature, is an excellent candidate for thermophilic oxidoreductions. The robust and readily available ER homologue chromate reductase (CrS) was used as a model enzyme in the reduction of conjugated C=C double bonds.

The combination of CrS and [Cp*Rh(bpy)(H2O)]2+ provides a system much simpler than the classical ones and shows promising catalytic performance. Optimization and upscaling of the chemoenzymatic reduction system are currently underway.

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