Artificial redox coenzymes:: biomimetic analogues of NAD+

A range of biomimetic analogues of the nicotinamide nucleotide coenzymes NAD(P)(H) have been developed based on the structure of a triazine dye template. These biomimetic redox coenzymes are relatively straightforward and inexpensive to synthesise and display NAD(+)-like activity with different dehydrogenases, despite their apparently minimal structural similarity to the native coenzyme NAD(+). Horse liver alcohol dehydrogenase oxidises butan-1-ol, using the most active biomimetic coenzyme (Nap 1), with a k(cat) value an order of magnitude lower and a K-m for the coenzyme two orders of magnitude higher than those using native NAD(+). The enzymatically reduced biomimetic coenzymes may be reoxidised by phenazine methosulfate. We believe that these coenzymes may find applications in biotransformations and biosensors, and in the development of biomimetic catalysts where the redox enzyme itself is replaced by a synthetic binding site.