Abstract
Asymmetric hydrogenation of activated alkenes catalysed by ene-reductases from the old yellow enzyme family (OYEs) leading to chiral products is of potential interest for industrial processes. OYEs’ dependency on the pyridine nucleotide coenzyme can be circumvented through established artificial hydride donors such as nicotinamide coenzyme biomimetics (NCBs). Several OYEs were found to exhibit higher reduction rates with NCBs. In this review, we describe a new classification of OYEs into three main classes by phylogenetic and structural analysis of characterized OYEs. The family roots are linked with their use as chiral catalysts and their mode of action with NCBs. The link between bioinformatics (sequence analysis), biochemistry (structure–function analysis), and biocatalysis (conversion, enantioselectivity and kinetics) can enable an early classification of a putative ene-reductase and therefore the indication of the binding mode of various activated alkenes.
Highlights
The 2001 Nobel prize in chemistry awarded to William S
DrER and RmER are not an exception with respect to the non-thermostable OYE relatives YqjM, XenA, and OYERo2, all clustering in the thermophilic-like subclass. These OYEs have a proline content below 7%, and are mostly stabilized through single salt bridges. Due to these varieties in the thermophilic-like subclass, we suggest the classification be updated through a phylogenetic analysis of all biochemically characterized OYEs (Figure 2)
In agreement with a bi-bi ping-pong mechanism, great similarity exists among OYEs in the binding mode of the nicotinamide moiety of NADPH and phenolic inhibitors such as para-hydroxybenzaldehyde (p-HBA) (Figure 5) or para-nitrophenol (p-NP)
Summary
The 2001 Nobel prize in chemistry awarded to William S. A highly competitive tool for asymmetric trans-hydrogenation is the biocatalytic route using ene-reductases (ERs) of the old yellow enzyme family (OYEs, EC 1.6.99.1). The performance of these enzymes is of potential interest for industrial processes due to their high regio-, stereoand enantioselectivity, and an expanding substrate scope [5,6,7,8,9]. Flurbiprofen belongspain to the non-steroidal library of OYEs was used for the asymmetric reduction of β-cyanoacrylate esters to yield a precursor anti-inflammatory drugs (NSAIDs) and is used at the appearance of dental pain or sore throat. OYE-catalysed asymmetric hydrogenation of activated alkenes through a bi-bi ping-pong mechanism producing one to two chiral chiral centres.
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