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Literature summary for 1.5.3.12 extracted from
- Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis (2012), J. Biol. Chem., 287, 42972-42983.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time quantitative PCR expression analysis, expression in Pichia pastoris | Papaver somniferum |
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| additional information | baculo virus-induced gene silencing in planta using Agrobacterium tumefaciens strain GV3101 transfection to reduce DBOX transcript levels, real-time quantitative PCR expression analysis | Papaver somniferum |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.146 | - |
(S)-scoulerine | pH 8.8, 37°C | Papaver somniferum |  |
| 0.201 | - |
Dihydrosanguinarine | pH 8.8, 37°C | Papaver somniferum | |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (RS)-canadine + O2 | Papaver somniferum | - |
berberine + H2O2 | - |
? | |
| (RS)-tetrahydrocolumbamine + O2 | Papaver somniferum | - |
? | - |
? | |
| (RS)-tetrahydropalmitine + O2 | Papaver somniferum | - |
? | - |
? | |
| (RS)-tetrahydropapaverine + O2 | Papaver somniferum | - |
papaverine + H2O2 | - |
? | |
| (S)-scoulerine + O2 | Papaver somniferum | DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation | ? | - |
? | |
| (S)-stylopine + O2 | Papaver somniferum | - |
? | - |
? | |
| dihydrochelerythrine + O2 | Papaver somniferum | - |
chelerythine + H2O2 | - |
? | |
| dihydrosanguinarine + O2 | Papaver somniferum | best substrate | sanguinarine + H2O2 | - |
? | |
| additional information | Papaver somniferum | the recombinant enzyme preferentially catalyzes the oxidation of dihydrosanguinarine to sanguinarine but also converts (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine | ? | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Papaver somniferum | - |
- |
- |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| flower bud | very low level compared to roots | Papaver somniferum | - |
| leaf | very low level compared to roots | Papaver somniferum | - |
| additional information | enzyme expression patterns, overview | Papaver somniferum | - |
| root | predominantly | Papaver somniferum | - |
| seedling | - |
Papaver somniferum | - |
| stem | very low level compared to roots | Papaver somniferum | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (RS)-canadine + O2 | - |
Papaver somniferum | berberine + H2O2 | - |
? | |
| (RS)-tetrahydrocolumbamine + O2 | - |
Papaver somniferum | ? | - |
? | |
| (RS)-tetrahydropalmitine + O2 | - |
Papaver somniferum | ? | - |
? | |
| (RS)-tetrahydropapaverine + O2 | - |
Papaver somniferum | papaverine + H2O2 | - |
? | |
| (RS)-tetrahydropapaverine + O2 | - |
Papaver somniferum | ? | - |
? | |
| (S)-scoulerine + O2 | DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation | Papaver somniferum | ? | - |
? | |
| (S)-stylopine + O2 | - |
Papaver somniferum | ? | - |
? | |
| dihydrochelerythrine + O2 | - |
Papaver somniferum | chelerythine + H2O2 | - |
? | |
| dihydrochelerythrine + O2 | - |
Papaver somniferum | ? | - |
? | |
| dihydrosanguinarine + O2 | best substrate | Papaver somniferum | sanguinarine + H2O2 | - |
? | |
| additional information | substrate specificity, overview | Papaver somniferum | ? | - |
? | |
| additional information | the recombinant enzyme preferentially catalyzes the oxidation of dihydrosanguinarine to sanguinarine but also converts (RS)-tetrahydropapaverine to papaverine and several protoberberine alkaloids to oxidized forms, including (RS)-canadine to berberine | Papaver somniferum | ? | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| DBOX | - |
Papaver somniferum |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 37 | - |
assay at | Papaver somniferum |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 8.8 | - |
assay at | Papaver somniferum |
Cofactor
| Cofactor | Comment | Organism | Structure |
|---|---|---|---|
| FAD | flavoprotein | Papaver somniferum | |
General Information
| General Information | Comment | Organism |
|---|---|---|
| malfunction | virus-induced gene silencing to reduce DBOX transcript levels results in a corresponding reduction in sanguinarine, dihydrosanguinarine, and papaverine accumulation in opium poppy roots | Papaver somniferum |
| metabolism | DBOX as a multifunctional oxidative enzyme in benzylisoquinoline alkaloid metabolism, overview. The two-electron oxidation of dihydrosanguinarine catalyzed by dihydrobenzophenanthridine oxidase is the final step in sanguinarine biosynthesis. The formation of the fully conjugated ring system in sanguinarine is similar to the four-electron oxidations of (S)-canadine to berberine and (S)-tetrahydropapaverine to papaverine | Papaver somniferum |
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Release 2023.1 (January 2023)
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