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Literature summary for 1.1.1.317 extracted from
- Enantioselective reduction of alpha,beta-unsaturated ketones and aryl ketones by perakine reductase (2019), Org. Lett., 21, 4411-4414 .
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| gene PR, functional recombinant expression of His-tagged enzyme in Escherichia coli | Rauvolfia serpentina |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 3.22 | - |
4-Nitroacetophenone | recombinant enzyme, pH and temperature not specified in the publication | Rauvolfia serpentina |  |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| perakine + NADPH + H+ | Rauvolfia serpentina | - |
raucaffrinoline + NADP+ | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Rauvolfia serpentina | Q3L181 | - |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography | Rauvolfia serpentina |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| 4-nitroacetophenone + NADPH + H+ | - |
Rauvolfia serpentina | 4-nitrobenzylalcohol + NADP+ | - |
? | |
| 4-nitrobenzaldehyde + NADPH + H+ | - |
Rauvolfia serpentina | 4-nitrobenzoate + NADP+ | - |
? | |
| additional information | enantioselective 1,2-reduction of alpha,beta-unsaturated ketones and aryl ketones by perakine reductase. Perakine reductase catalyzes asymmetric reduction of enones and aromatic ketones, leading to alpha-allylic alcohols and alpha-aromatic alcohols. It is NADPH-dependent. Among the evaluated substances, 4'-nitroacetophenone is found to be the best ketone substrate, with yield and enantiomeric excess values exceeding 99%. Exclusive enantioselectivity of enzyme perakine reductase (PR) | Rauvolfia serpentina | ? | - |
- |
|
| perakine + NADPH + H+ | - |
Rauvolfia serpentina | raucaffrinoline + NADP+ | - |
? | |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| NADPH | - |
Rauvolfia serpentina | |
General Information
| General Information | Comment | Organism |
|---|---|---|
| evolution | the enzyme is a member of aldo-ketone reductase (AKR) 13D family | Rauvolfia serpentina |
| additional information | molecular modeling of the reaction mechansim. In the model, the oxygen atom of the product's hydroxy group approaches the carboxamide group of NADPH, located within a hydrogen-bond distance of the gamma-N of the imidazole ring of His126. Substrate binding analysis: the large pocket is formed by the surface of residues Ile56, Ile87, Ile 90, His126, and Arg127, the three clustered Ile residues contributing to the hydrophobic property of the pocket may facilitate substrate binding, the small pocket comprises the surface of the Met21, Tyr57, and Lys84 residues, together with the nicotinamide riboside component of NADPH | Rauvolfia serpentina |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.08 | - |
4-Nitroacetophenone | recombinant enzyme, pH and temperature not specified in the publication | Rauvolfia serpentina | |
| 29.5 | - |
4-nitrobenzaldehyde | recombinant enzyme, pH and temperature not specified in the publication | Rauvolfia serpentina | |
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