Information on EC 1.5.3.12 - dihydrobenzophenanthridine oxidase

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The expected taxonomic range for this enzyme is: Papaveraceae

EC NUMBER
COMMENTARY
1.5.3.12
-
RECOMMENDED NAME
GeneOntology No.
dihydrobenzophenanthridine oxidase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
dihydrochelirubine + O2 = chelirubine + H2O2
show the reaction diagram
-
-
-
-
dihydromacarpine + O2 = macarpine + H2O2
show the reaction diagram
-
-
-
-
dihydrosanguinarine + O2 = sanguinarine + H2O2
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
reduction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
Isoquinoline alkaloid biosynthesis
-
Metabolic pathways
-
sanguinarine and macarpine biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
dihydrobenzophenanthridine:oxygen oxidoreductase
A CuII enzyme found in higher plants that produces oxidized forms of the benzophenanthridine alkaloids
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
DHBP
-
-
-
-
Oxidase, dihydrobenzophenanthridine
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
114051-83-1
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
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
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
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(RS)-canadine + O2
berberine + H2O2
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydrocolumbamine + O2
?
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydropalmitine + O2
?
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydropapaverine + O2
papaverine + H2O2
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydropapaverine + O2
?
show the reaction diagram
-
-
-
-
?
(S)-scoulerine + O2
?
show the reaction diagram
-
DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation
-
-
?
(S)-stylopine + O2
?
show the reaction diagram
-
-
-
-
?
dihydrochelerythrine + O2
chelerythrine + H2O2
show the reaction diagram
-
-
-
-
-
dihydrochelerythrine + O2
chelerythine + H2O2
show the reaction diagram
-
-
-
-
?
dihydrochelerythrine + O2
?
show the reaction diagram
-
-
-
-
?
dihydrochelirubine + O2
chelirubine + H2O2
show the reaction diagram
-
-
-
-
Dihydromacarpine + O2
Macarpine + H2O2
show the reaction diagram
-
-
-
-
Dihydromacarpine + O2
?
show the reaction diagram
-
terminal step in the formation of benzophenanthridine alkaloids containing methylene dioxy substitutions in ring A and D
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
best substrate
-
-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
last step in the biogenesis of sanguinarine, induced in a dose-dependent and time-dependent manner up to 4fold to 14fold, respectively when the cells are treated with jasmonate or with acetylsalicylic acid
-
-
-
additional information
?
-
-
no reaction with: dihydronorsanguinarine, ajmalicine
-
-
-
additional information
?
-
-
substrate specificity, overview
-
-
-
additional information
?
-
-
one of the enzymes that catalyzes a later step in the biogenesis of benzo(c)phenanthridine alkaloids
-
-
-
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
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(RS)-canadine + O2
berberine + H2O2
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydrocolumbamine + O2
?
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydropalmitine + O2
?
show the reaction diagram
-
-
-
-
?
(RS)-tetrahydropapaverine + O2
papaverine + H2O2
show the reaction diagram
-
-
-
-
?
(S)-scoulerine + O2
?
show the reaction diagram
-
DBOX does not fully aromatize the C-ring of (S)-scoulerine but instead catalyzes a two-electron oxidation
-
-
?
(S)-stylopine + O2
?
show the reaction diagram
-
-
-
-
?
dihydrochelerythrine + O2
chelerythine + H2O2
show the reaction diagram
-
-
-
-
?
Dihydromacarpine + O2
?
show the reaction diagram
-
terminal step in the formation of benzophenanthridine alkaloids containing methylene dioxy substitutions in ring A and D
-
-
-
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
best substrate
-
-
?
dihydrosanguinarine + O2
sanguinarine + H2O2
show the reaction diagram
-
last step in the biogenesis of sanguinarine, induced in a dose-dependent and time-dependent manner up to 4fold to 14fold, respectively when the cells are treated with jasmonate or with acetylsalicylic acid
-
-
-
additional information
?
-
-
one of the enzymes that catalyzes a later step in the biogenesis of benzo(c)phenanthridine alkaloids
-
-
-
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
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
FAD
-
flavoprotein
flavin
-
inhibition pattern indicates the presence of bound flavine
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
copper
-
might be a copper metalloenzyme
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
1,4-DL-dithiothreitol
-
-
diethyldithiocarbamate
-
-
mercaptoethanol
-
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.146
-
(S)-scoulerine
-
pH 8.8, 37°C
0.012
-
Dihydrochelerythrine
-
-
0.008
-
dihydrochelirubine
-
-
0.006
-
Dihydromacarpine
-
-
0.006
-
Dihydromacarpine
-
dihydrosanguinarine
0.016
-
Dihydrosanguinarine
-
-
0.201
-
Dihydrosanguinarine
-
pH 8.8, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
-
additional information
-
-
-
additional information
-
-
sensitive, rapid and convenient fluorimetric assay
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
8.8
-
-
assay at
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.5
8
-
about 50% of maximal activity at pH 5.5 and 8.0
6
8.5
-
about 50% of maximal activity at pH 6.0 and 8.5
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37
-
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
elicited cell suspension
Manually annotated by BRENDA team
-
elicited cell suspension; elicited tissues
Manually annotated by BRENDA team
-
elicited cell suspension
Manually annotated by BRENDA team
-
very low level compared to roots
Manually annotated by BRENDA team
-
predominantly
Manually annotated by BRENDA team
-
very low level compared to roots
Manually annotated by BRENDA team
-
very low level compared to roots
Manually annotated by BRENDA team
additional information
-
enzyme expression patterns, overview
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
56000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
a major component of MW 77000 and two minor components with MW between 59000 and 67000 are detected by SDS-PAGE
?
-
x * 77000, SDS-PAGE, the lower MW bands include enzymes of the polyphenol oxidase family that copurify with dihydrobenzophenanthridine oxidase
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time quantitative PCR expression analysis, expression in Pichia pastoris
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
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