Information on EC 1.3.3.8 - tetrahydroberberine oxidase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.3.8
-
RECOMMENDED NAME
GeneOntology No.
tetrahydroberberine oxidase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-tetrahydroberberine + 2 O2 = berberine + 2 H2O2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
berberine biosynthesis
-
-
Isoquinoline alkaloid biosynthesis
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
(S)-tetrahydroberberine:oxygen oxidoreductase
The enzyme from Berberis sp. is a flavoprotein; that from Coptis japonica is not. (R)-Tetrahydroberberines are not oxidized.
CAS REGISTRY NUMBER
COMMENTARY hide
114705-00-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Berberis wilsoniae
var. subcaulialata
-
-
Manually annotated by BRENDA team
gene Cs(S)-THBO
UniProt
Manually annotated by BRENDA team
wood tumeric
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Thalictrum dipterocarpum Franch.
-
-
-
Manually annotated by BRENDA team
Thalictrum flavum ssp. glaucum
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-canadine + O2
?
show the reaction diagram
Berberis wilsoniae
-
-
-
-
?
(S)-tetrahydroberberine + 2 O2
berberine + 2 H2O2
show the reaction diagram
(S)-tetrahydroberberine + O2
berberine + H2O2 + H2O
show the reaction diagram
(S)-tetrahydroberberine + O2
protoberberine + H2O2 + H2O
show the reaction diagram
Berberis wilsoniae
-
7,14-dehydroberberinium as intermediate, protoberberine biosynthesis
-
?
(S)-tetrahydrojatrorrhizine + O2
?
show the reaction diagram
Berberis wilsoniae
-
-
-
-
?
(S,R)-tetrahydrojatrorrhizine + O2
jatrorrhizine + H2O2
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(S)-tetrahydroberberine + 2 O2
berberine + 2 H2O2
show the reaction diagram
(S)-tetrahydroberberine + O2
berberine + H2O2 + H2O
show the reaction diagram
-
final step in berberine biosynthesis
-
?
(S)-tetrahydroberberine + O2
protoberberine + H2O2 + H2O
show the reaction diagram
Berberis wilsoniae
-
7,14-dehydroberberinium as intermediate, protoberberine biosynthesis
-
?
additional information
?
-
E3WDH1
the recombinant enzyme expressed in transgenic Eschscholzia californica cells produces coptisine and dehydrocheilanthifoline from pathway intermediates cheilanthifoline and stylopine, overview
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
flavin
Berberis wilsoniae
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cu2+
-
CuSO4, enhances enzyme activity
additional information
-
different metallic ions studied
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
aminoethoxyvinylglycine
-
-
bathophenanthroline sulfonic acid
-
specific Fe2+ ion chelator, more than 1 mM required for 50% inhibition at an enzyme concentration of 0.0003 mM
Morine
Berberis wilsoniae
-
50% inhibition at 0.00018 mM
[Ag(S2O3)2]3-
-
silver thiosulfate
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ethylene
-
activates berberine biosythesis
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0267
(S)-canadine
Berberis wilsoniae
-
-
0.0021 - 0.0267
(S)-tetrahydroberberine
0.0013
(S)-Tetrahydrojatrorrhizine
Berberis wilsoniae
-
-
0.001
tetrahydroberberine
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
8.1 nkat/mg protein
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.8
-
50 mM phosphate buffer and borate buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
biosynthesis leading to berberine takes place in special vesicles
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
58000
-
gel filtration
100000
145000
-
isoenzyme II, gel filtration
155000
-
gel filtration
200000
-
higher than, isoenzyme I, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 28000, SDS-PAGE
trimer
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
-
50% loss of activity after 20 h
45
-
1 h, 40% loss of activity
50
-
1 h, 90% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
instable
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 50% loss of activity after 20 h
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
Berberis wilsoniae
-
copurification of three isoforms by ion-exchange
-
ion-exchange, gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cDNA is expressed in Escherichia coli DH5alpha
-
DNA and amino acid sequence determination and analysis, functional ectopical expression of CjTHBO under the control of Cauliflower mosaic virus 35S promoterin Eschscholzia californica cells via transformation with Agrobacterium tumefaciens strain LBA4404. The transgenic cells produce coptisine and dehydrocheilanthifoline, which are expected to be generated by the reaction of CjTHBO from pathway intermediates, i.e. cheilanthifoline and stylopine, alkaloid profile analysis in transgenic California poppy cells, overview. Expression in Escherichia coli strain BL21 (DE3)
gene Cs(S)-THBO, DNA and amino acid sequence determination and analysis, real-time quantitative PCR analysis, tissue expression profiling analyses, expression of the His-tagged enzyme in Escherichia coli strain BL21 (DE3)