Cloned (Comment) | Organism |
---|---|
gene CYP5437, unrooted neighbor-joining phylogenetic tree, recombinant expression | Rauvolfia serpentina |
KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|
additional information | - |
additional information | Michaelis-Menten-type reaction kinetics | Rauvolfia serpentina | |
0.0068 | - |
vinorine | pH 6.5, 30°C, recombinant enzyme | Rauvolfia serpentina |
Localization | Comment | Organism | GeneOntology No. | Textmining |
---|---|---|---|---|
microsome | - |
Rauvolfia serpentina | - |
- |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
additional information | Rauvolfia serpentina | the enzyme also catalyzes the non-oxidative isomerization of the ajmaline precursor vomilenine to perakine | additional information | - |
? | |
vinorine + [reduced NADPH-hemoprotein reductase] + O2 | Rauvolfia serpentina | - |
vomilenine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Rauvolfia serpentina | A0A218NGS0 | - |
- |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
additional information | the enzyme also catalyzes the non-oxidative isomerization of the ajmaline precursor vomilenine to perakine | Rauvolfia serpentina | ? | - |
? | |
additional information | product analysis by NMR spectroscopy. The stereoselectivity of the enzyme cannot be determined, since the vomilenine isomers cannot be separated | Rauvolfia serpentina | ? | - |
? | |
additional information | the enzyme also catalyzes the non-oxidative isomerization of the ajmaline precursor vomilenine to perakine | Rauvolfia serpentina | additional information | - |
? | |
vinorine + [reduced NADPH-hemoprotein reductase] + O2 | - |
Rauvolfia serpentina | vomilenine + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? |
Synonyms | Comment | Organism |
---|---|---|
CYP5437 | - |
Rauvolfia serpentina |
CYP82S18 | - |
Rauvolfia serpentina |
cytochrome P450_5437 | - |
Rauvolfia serpentina |
vinorine hydroxylase | - |
Rauvolfia serpentina |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
30 | - |
- |
Rauvolfia serpentina |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
6.5 | - |
hydroxylation reaction | Rauvolfia serpentina |
Cofactor | Comment | Organism | Structure |
---|---|---|---|
cytochrome P-450 | - |
Rauvolfia serpentina | |
NADPH-hemoprotein reductase | A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._ | Rauvolfia serpentina |
General Information | Comment | Organism |
---|---|---|
metabolism | in plant-derived ajmalan alkaloid pathways, the biosynthetic intermediate vomilenine can be transformed into the anti-arrhythmic compound ajmaline, or alternatively, can isomerize to form perakine, an alkaloid with a structurally distinct scaffold. Enzyme vinorine hydroxylase, a cytochrome P450 enzyme, hydroxylates vinorine to form vomilenine, which exists as a mixture of rapidly interconverting epimers (with 21-epi-vomilenine). The cytochrome P450 also catalyzes the non-oxidative isomerization of the ajmaline precursor vomilenine to perakine. Alkaloid network in Rauwolfia serpentina from strictosidine, overview | Rauvolfia serpentina |
additional information | proposed reaction mechanism for the isomerization of vomilenine to perakine, the introduction of a hydroxy group at C-21 allows opening of the ring via the newly formed hemiaminal. The resulting amine can then undergo a Michael addition to form perakine, overview. The conversion of vomilenine into perakine is enzymatically catalyzed by vinorine hydroxylase | Rauvolfia serpentina |
physiological function | the unusual dual catalytic activity of vinorine hydroxylase provides a control mechanism for the bifurcation of the alkaloid pathway branches | Rauvolfia serpentina |