Better than Nature: Nicotinamide Biomimetics That Outperform Natural Coenzymes
Tanja Knaus,Caroline E. Paul,Colin Levy,Simon de Vries,Francesco G. Mutti,Frank Hollmann,Nigel S. Scrutton +6 more
TL;DR: The efficiency of man-made synthetic biomimetics of the natural coenzymes NAD(P)H in redox biocatalysis is investigated and it is shown that in selected cases, these biomimetic outperform the naturalcoenzymes.
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Abstract: The search for affordable, green biocatalytic processes is a challenge for chemicals manufacture. Redox biotransformations are potentially attractive, but they rely on unstable and expensive nicotinamide coenzymes that have prevented their widespread exploitation. Stoichiometric use of natural coenzymes is not viable economically, and the instability of these molecules hinders catalytic processes that employ coenzyme recycling. Here, we investigate the efficiency of man-made synthetic biomimetics of the natural coenzymes NAD(P)H in redox biocatalysis. Extensive studies with a range of oxidoreductases belonging to the “ene” reductase family show that these biomimetics are excellent analogues of the natural coenzymes, revealed also in crystal structures of the ene reductase XenA with selected biomimetics. In selected cases, these biomimetics outperform the natural coenzymes. “Better-than-Nature” biomimetics should find widespread application in fine and specialty chemicals production by harnessing the power...
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References
On the active site of Old Yellow Enzyme. Role of histidine 191 and asparagine 194.
TL;DR: In this paper, Fox et al. used the crystal structure of OYE1 from brewer's bottom yeast to identify histidine 191 and asparagine 194 as amino acid residues that hydrogen-bond with the phenolic ligands, stabilizing the anionic form involved in charge-transfer interaction with the FMN prosthetic group.
145
Comparison of three enoate reductases and their potential use for biotransformations
Javier F Chaparro-Riggers,Thomas A. Rogers,Eduardo Vazquez-Figueroa,Karen M. Polizzi,Andreas S. Bommarius +4 more
TL;DR: The wide specificity of enoate reductases for a range of α,β-unsaturated carbonyl compounds as well as coupling to glucose dehydrogenase for recycling of NAD(P)(H); however, the stability limitations the authors found need to be overcome to envision large-scale use of ERs in synthesis.
144
Is Simpler Better? Synthetic Nicotinamide Cofactor Analogues for Redox Chemistry
TL;DR: An overview of the synthesis, mechanism, and applications of nicotinamide cofactor NAD(P)H analogues in redox chemistry, particularly 1,4-dihydronicotinamide derivatives and their oxidized counterpart, is presented.
143
Sequence and properties of pentaerythritol tetranitrate reductase from Enterobacter cloacae PB2.
TL;DR: Pentaerythritol tetranitrate reductase, which reductively liberates nitrite from nitrate esters, is related to old yellow enzyme and follows a ping-pong mechanism with competitive substrate inhibition by NADPH and is capable of reducing the unsaturated bond of 2-cyclohexen-1-one.
New developments in ‘ene’-reductase catalysed biological hydrogenations
TL;DR: This review will focus on progress in this field within the last two years, with emphasis on industrial applications of asymmetric biocatalytic hydrogenations.
141