Information on EC 1.13.11.71 - carotenoid-9',10'-cleaving dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.71
-
RECOMMENDED NAME
GeneOntology No.
carotenoid-9',10'-cleaving dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
all-trans-beta-carotene + O2 = all-trans-10'-apo-beta-carotenal + beta-ionone
show the reaction diagram
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-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
carotenoid cleavage
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SYSTEMATIC NAME
IUBMB Comments
all-trans-beta-carotene:O2 oxidoreductase (9',10'-cleaving)
Requires Fe2+. The enzyme catalyses the asymmetric oxidative cleavage of carotenoids. The mammalian enzyme can also cleave all-trans-lycopene.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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A3KN98
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
9-cis-beta-carotene + O2
9-cis-beta-apo-10'-carotenal + beta-ionone
show the reaction diagram
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-
-
?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
show the reaction diagram
alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
show the reaction diagram
beta-carotene + O2
10'-apo-beta-carotenal + beta-ionone
show the reaction diagram
-
-
-
?
beta-carotene + O2
10'-apo-carotenal + beta-ionone
show the reaction diagram
beta-cryptoxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + beta-ionone
show the reaction diagram
-
-
-
?
beta-cryptoxanthin + O2
3-hydroxy-beta-apo-8'-carotenal + beta-cyclocitral
show the reaction diagram
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-
-
?
beta-cryptoxanthin + O2
beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
show the reaction diagram
-
-
-
?
beta-cryptoxanthin + O2
beta-apo-10'-carotenal + ?
show the reaction diagram
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main clevage product is beta-apo-10'-carotenal only small amounts of 3-OH-beta-apocarotenal are formed
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-
?
canthaxanthin + O2
?
show the reaction diagram
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-
-
-
?
lutein + O2
3-hydroxy-alpha-apo-10'-carotenal + 3-hydroxy-beta-ionone
show the reaction diagram
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-
-
?
lutein + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-alpha-ionone
show the reaction diagram
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-
-
?
lutein + O2
?
show the reaction diagram
lycopene + O2
?
show the reaction diagram
-
-
-
-
?
meso-zeaxanthin + O2
?
show the reaction diagram
zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
show the reaction diagram
additional information
?
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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
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
show the reaction diagram
alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
show the reaction diagram
lutein + O2
?
show the reaction diagram
meso-zeaxanthin + O2
?
show the reaction diagram
zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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activates by 26% at 5 mM
Cu2+
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activates by 23% at 5 mM
Mg2+
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activates by 14% at 5 mM
Ni2+
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activates by 7% at 5 mM
Zn2+
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activates by 17% at 5 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-oxo-N-(4-hydroxyphenyl)-all-trans-retinamide
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EDTA
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inhibits by 10% at 5 mM
Fe2+
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inhibits by 37% at 5 mM
Mn2+
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inhibits by 13% at 5 mM
SDS
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99% inhibition at 1 %
Urea
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86% inhibition at 4 M
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
DTT
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activates by 27% at 5 mM
methanol
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addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
Triton X-100
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activates by 7% at 1% w/v
Tween 20
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activates by 3% at 1% w/v
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.037
all-trans-beta-carotene
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pH 8.0, 45°C
0.048
alpha-carotene
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pH 8.0, 45°C
0.0152 - 0.067
beta-carotene
0.105
lutein
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pH 8.0, 45°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0475
all-trans-beta-carotene
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pH 8.0, 45°C
0.0392
alpha-carotene
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pH 8.0, 45°C
0.0053
beta-carotene
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pH 8.0, 37°C
0.0167
lutein
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pH 8.0, 45°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.284
all-trans-beta-carotene
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pH 8.0, 45°C
0.817
alpha-carotene
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pH 8.0, 45°C
0.079
beta-carotene
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pH 8.0, 37°C
0.159
lutein
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pH 8.0, 45°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.38
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purified native enzyme, pH 8.0, 45°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9
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50 % of the maximal activity at pH 7.0 and pH 9.0, 20% at pH 6.0 and pH 9.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28
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assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 65
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activity range, profile overview
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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endometrial connective tissue
Manually annotated by BRENDA team
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low abundance of mRNA
Manually annotated by BRENDA team
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pectoralis major
Manually annotated by BRENDA team
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epithelium
Manually annotated by BRENDA team
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expression of the bco2 gene is dramatically decreased in prostate cancer tissue and in a range of prostate cancer cell lines as compared with nonneoplastic prostate tissue and normal prostatic epithelial cells, respectively. DNA methyltransferase inhibition induces bco2 expression in prostate cancer cells
Manually annotated by BRENDA team
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prostate connective tissue
Manually annotated by BRENDA team
predominant expression
Manually annotated by BRENDA team
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mucosa of stomach
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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protein contains a probable chloroplast targeting sequence of 31 amino acids
Manually annotated by BRENDA team
additional information
A3KN98;
subcellular expression and localization of BCO1 and BCO2 proteins in rat liver and intestine, overview
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Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
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half-life 326 min
40
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half-life 247 min
45
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half-life 191 min
50
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half-life 84 min
55
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half-life 22 min
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2-butanone
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inhibits 66% at 50 v/v
Acetone
benzene
chloroform
dichloromethane
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inhibits 49% at 50 v/v
dimethylformamide
DMSO
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inhibits 17% at 50 v/v
Methanol
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addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
toluene
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a small amount of recombinant, catalytically inactive His-tagged enzyme from Escherichia coli strain BL21-Gold (DE3) by cobalt affinity chromatography
native enzyme 9.5fold to homogeneity by ammonium sulfate fractionation and gel filtration
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recombinant His-tagged enzyme from Escherichia coli strain BL21-Gold (DE3) by cobalt affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expression in Escherichia coli
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gene BCDO2, quantitative PCR enzyme expression analysis
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gene bco2, recombinant expression in Escherichia coli
gene BCO2, sequence comparisons, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21-Gold (DE3)
gene BCO2, sequence comparisons, recombinant expression of His-tagged, catalytically inactive enzyme BCO2 in Escherichia coli strain BL21-Gold (DE3), mostly in inclusion bodies
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
a marked up-regulation of Bcdo2 expression in inguinal white adipose tissue of Bcmo1-null mice is shown, both with control and beta-carotene diet
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expression of the bco2 gene is dramatically decreased in prostate cancer tissue and in a range of prostate cancer cell lines as compared with nonneoplastic prostate tissue and normal prostatic epithelial cells, respectively. Inhibition of DNA methyltransferase activity restores bco2 expression in prostate cancer cell lines tested
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treatment with lycopene or its metabolite, apo-10-lycopenal, increases bco2 expression and reduces cell proliferation in androgen-sensitive cell lines, but lycopene neither alters bco2 expression nor cell growth in androgen-resistant cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
a nonsense mutation c.196C>T in the beta-carotene oxygenase 2 gene is found to strongly associate with the yellow fat phenotype in sheep. The existence of individuals lacking this mutation, but still demonstrating yellow fat, suggests that additional mutations may cause a similar phenotype in this population. Animals homozygous for the mutation are not reported to suffer from any negative health or development traits, pointing towards a minor role of BCO2 in vitamin A formation
synthesis