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

Org Lett. 2013 Jan 4;15(1):180-3. doi: 10.1021/ol303240a. Epub 2012 Dec 20.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Molecular Mimicry
  • Molecular Structure
  • NAD / chemistry
  • NAD / metabolism
  • Niacinamide / chemical synthesis*
  • Niacinamide / chemistry
  • Oxidoreductases Acting on CH-CH Group Donors / chemistry
  • Oxidoreductases Acting on CH-CH Group Donors / metabolism*

Substances

  • NAD
  • Niacinamide
  • Oxidoreductases Acting on CH-CH Group Donors
  • 2-enoate reductase