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Literature summary extracted from

  • Hagel, J.M.; Beaudoin, G.A.; Fossati, E.; Ekins, A.; Martin, V.J.; Facchini, P.J.
    Characterization of a flavoprotein oxidase from opium poppy catalyzing the final steps in sanguinarine and papaverine biosynthesis (2012), J. Biol. Chem., 287, 42972-42983.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.5.3.12 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

EC Number Protein Variants Comment Organism
1.5.3.12 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]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.5.3.12 0.146
-
 (S)-scoulerine pH 8.8, 37°C Papaver somniferum
1.5.3.12 0.201
-
 Dihydrosanguinarine pH 8.8, 37°C Papaver somniferum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.5.3.12 (RS)-canadine + O2 Papaver somniferum
-
 berberine + H2O2
-
 ?
1.5.3.12 (RS)-tetrahydrocolumbamine + O2 Papaver somniferum
-
 ?
-
 ?
1.5.3.12 (RS)-tetrahydropalmitine + O2 Papaver somniferum
-
 ?
-
 ?
1.5.3.12 (RS)-tetrahydropapaverine + O2 Papaver somniferum
-
 papaverine + H2O2
-
 ?
1.5.3.12 (S)-scoulerine + O2 Papaver somniferum DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation ?
-
 ?
1.5.3.12 (S)-stylopine + O2 Papaver somniferum
-
 ?
-
 ?
1.5.3.12 dihydrochelerythrine + O2 Papaver somniferum
-
 chelerythine + H2O2
-
 ?
1.5.3.12 dihydrosanguinarine + O2 Papaver somniferum best substrate sanguinarine + H2O2
-
 ?
1.5.3.12 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

EC Number Organism UniProt Comment Textmining
1.5.3.12 Papaver somniferum
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.5.3.12 flower bud very low level compared to roots Papaver somniferum
-
1.5.3.12 leaf very low level compared to roots Papaver somniferum
-
1.5.3.12 additional information enzyme expression patterns, overview Papaver somniferum
-
1.5.3.12 root predominantly Papaver somniferum
-
1.5.3.12 seedling
-
 Papaver somniferum
-
1.5.3.12 stem very low level compared to roots Papaver somniferum
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.5.3.12 (RS)-canadine + O2
-
 Papaver somniferum berberine + H2O2
-
 ?
1.5.3.12 (RS)-tetrahydrocolumbamine + O2
-
 Papaver somniferum ?
-
 ?
1.5.3.12 (RS)-tetrahydropalmitine + O2
-
 Papaver somniferum ?
-
 ?
1.5.3.12 (RS)-tetrahydropapaverine + O2
-
 Papaver somniferum papaverine + H2O2
-
 ?
1.5.3.12 (RS)-tetrahydropapaverine + O2
-
 Papaver somniferum ?
-
 ?
1.5.3.12 (S)-scoulerine + O2 DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation Papaver somniferum ?
-
 ?
1.5.3.12 (S)-stylopine + O2
-
 Papaver somniferum ?
-
 ?
1.5.3.12 dihydrochelerythrine + O2
-
 Papaver somniferum chelerythine + H2O2
-
 ?
1.5.3.12 dihydrochelerythrine + O2
-
 Papaver somniferum ?
-
 ?
1.5.3.12 dihydrosanguinarine + O2 best substrate Papaver somniferum sanguinarine + H2O2
-
 ?
1.5.3.12 additional information substrate specificity, overview Papaver somniferum ?
-
 ?
1.5.3.12 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

EC Number Synonyms Comment Organism
1.5.3.12 DBOX
-
 Papaver somniferum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.5.3.12 37
-
 assay at Papaver somniferum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.5.3.12 8.8
-
 assay at Papaver somniferum

Cofactor

EC Number Cofactor Comment Organism Structure
1.5.3.12 FAD flavoprotein Papaver somniferum

General Information

EC Number General Information Comment Organism
1.5.3.12 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
1.5.3.12 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