Information on EC 1.14.13.129 - beta-carotene 3-hydroxylase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea

EC NUMBER
COMMENTARY hide
1.14.13.129
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RECOMMENDED NAME
GeneOntology No.
beta-carotene 3-hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
beta-carotene + 2 NADH + 2 H+ + 2 O2 = zeaxanthin + 2 NAD+ + 2 H2O
show the reaction diagram
overall reaction
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-
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beta-carotene + NADH + H+ + O2 = beta-cryptoxanthin + NAD+ + H2O
show the reaction diagram
(1a)
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-
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beta-cryptoxanthin + NADH + H+ + O2 = zeaxanthin + NAD+ + H2O
show the reaction diagram
(1b)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
astaxanthin biosynthesis (bacteria, fungi, algae)
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astaxanthin biosynthesis (flowering plants)
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carotenoid biosynthesis
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Carotenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
beta-carotene,NADH:oxygen 3-oxidoreductase
Requires ferredoxin and Fe(II). Also acts on other carotenoids with a beta-end group. In some species canthaxanthin is the preferred substrate.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
Kaki persimmon
UniProt
Manually annotated by BRENDA team
yellow gentian
UniProt
Manually annotated by BRENDA team
Haematococcus pluvialis
cultivar Shinhwangmi
UniProt
Manually annotated by BRENDA team
cultivar Red Setter
UniProt
Manually annotated by BRENDA team
the sexual state of Phaffia rhodozyma
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
3'-hydroxyechinenone + NADH + H+ + O2
4-ketozeaxanthin + NAD+ + H2O
show the reaction diagram
-
-
4-ketozeaxanthin is adonixanthin
-
?
3'-hydroxyechinenone + NADH + H+ + O2
adonixanthin + NAD+ + H2O
show the reaction diagram
3-hydroxyechinenone + NADH + H+ + O2
4-ketozeaxanthin + NAD+ + H2O
show the reaction diagram
-
-
4-ketozeaxanthin is adonixanthin
-
?
3-hydroxyechinenone + NADH + H+ + O2
adonixanthin + NAD+ + H2O
show the reaction diagram
adonirubin + NADH + H+ + O2
astaxanthin + NAD+ + H2O
show the reaction diagram
adonirubin + NADPH + H+ + O2
astaxanthin + NADP+ + H2O
show the reaction diagram
alpha-carotene + 2 NADH + 2 H+ + 2 O2
zeinoxanthin + 2 NAD+ + 2 H2O
show the reaction diagram
-
-
-
-
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alpha-carotene + NADH + H+ + O2
lutein + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
alpha-carotene + NADH + H+ + O2
zeinoxanthin + NAD+ + H2O
show the reaction diagram
beta-carotene + 2 NADH + 2 H+ + 2 O2
zeaxanthin + 2 NAD+ + 2 H2O
show the reaction diagram
beta-carotene + 2 NADH + 2 H+ + 2 O2
zeaxanthin + 2 NAD+ + H2O
show the reaction diagram
-
-
-
-
?
beta-carotene + 2 NADH + 2 H+ + 2 O2
zeaxanthin + 2 NADH + 2 H2O
show the reaction diagram
-
beta-carotene is only partly converted into zeaxanthin by Chx, though a major portion (75-80%) is left
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-
?
beta-carotene + 2 NADH + H+ + O2
zeaxanthin + 2 NAD+ + 2 H2O
show the reaction diagram
-
overall reaction
-
-
?
beta-carotene + 2 NADPH + 2 H+ + 2 O2
zeaxanthin + 2 NADP+ + 2 H2O
show the reaction diagram
beta-carotene + NADH + H+ + O2
?
show the reaction diagram
beta-carotene + NADH + H+ + O2
beta-cryptoxanthin + NAD+ + H2O
show the reaction diagram
beta-carotene + NADH + H+ + O2
cryptoxanthin + NAD+ + H2O
show the reaction diagram
beta-carotene + NADH + H+ + O2
zeaxanthin + NAD+ + H2O
show the reaction diagram
beta-carotene + NADH + H+ + O2
zeinoxanthin + NAD+ + H2O
show the reaction diagram
-
the enzyme prefers alpha-carotene over beta-carotene as a substrate
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-
?
beta-carotene + NADPH + H+ + O2
beta-cryptoxanthin + NADP+ + H2O
show the reaction diagram
beta-carotene + NADPH + H+ + O2
zeaxanthin + NADP+ + H2O
show the reaction diagram
beta-cryptoxanthin + NADH + H+ + O2
zeaxanthin + NAD+ + H2O
show the reaction diagram
beta-cryptoxanthin + NADPH + H+ + O2
zeaxanthin + NADP+ + H2O
show the reaction diagram
beta-zeacarotene + NADH + H+ + O2
hydroxy-beta-zeacarotene + NAD+ + H2O
show the reaction diagram
-
beta-zeacarotene is 7',8'-dihydro-beta,psi-carotene
hydroxy-beta-zeacarotene is 7',8'-dihydro-beta,psi-carotene-3-ol
-
?
canthaxanthin + NADH + H+ + O2
adonirubin + NAD+ + H2O
show the reaction diagram
canthaxanthin + NADH + H+ + O2
astaxanthin + NAD+ + H2O
show the reaction diagram
canthaxanthin + NADH + H+ + O2
phoenicoxanthin + NAD+ + H2O
show the reaction diagram
-
canthaxanthin is beta,beta-carotene-4-4'-dione
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-
?
canthaxanthin + NADPH + H+ + O2
adonirubin + NADP+ + H2O
show the reaction diagram
canthaxanthin + NADPH + H+ + O2
astaxanthin + NADP+ + H2O
show the reaction diagram
cryptoxanthin + NADH + H+ + O2
zeaxanthin + NAD+ + H2O
show the reaction diagram
echinenone + NADH + H+ + O2
3'-hydroxyechinenone + 3-hydroxyechinenone + NAD+ + H2O
show the reaction diagram
echinenone + NADH + H+ + O2
3'-hydroxyechinenone + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
echinenone + NADH + H+ + O2
3-hydroxyechinenone + NAD+ + H2O
show the reaction diagram
-
echinenone is beta,beta-carotene-4-one
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-
?
echinenone + NADH + H+ + O2
4-ketozeaxanthin + NAD+ + H2O
show the reaction diagram
-
conversion occurs via 3- and 3'-hydroxyechinenone
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-
?
phoenicoxanthin + NADH + H+ + O2
astaxanthin + NAD+ + H2O
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
alpha-carotene + NADH + H+ + O2
lutein + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
alpha-carotene + NADH + H+ + O2
zeinoxanthin + NAD+ + H2O
show the reaction diagram
-
-
-
-
?
beta-carotene + 2 NADH + 2 H+ + 2 O2
zeaxanthin + 2 NAD+ + 2 H2O
show the reaction diagram
B3SGL0
-
-
-
?
beta-carotene + NADH + H+ + O2
?
show the reaction diagram
beta-carotene + NADH + H+ + O2
beta-cryptoxanthin + NAD+ + H2O
show the reaction diagram
beta-carotene + NADH + H+ + O2
zeaxanthin + NAD+ + H2O
show the reaction diagram
beta-carotene + NADH + H+ + O2
zeinoxanthin + NAD+ + H2O
show the reaction diagram
-
the enzyme prefers alpha-carotene over beta-carotene as a substrate
-
-
?
beta-cryptoxanthin + NADH + H+ + O2
zeaxanthin + NAD+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ferredoxin
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NADPH
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8-hydroxyquinoline
5% residual activity at 1 mM
CHAPS
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1% (v/v) promotes inhibition of activity
cytochrome c
addition of cytochrome c to the incubation medium inhibits hydroxylase activity
deoxycholate
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1% (v/v) promotes inhibition of activity
NP-40
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1% (v/v) promotes inhibition of activity
o-phenanthroline
10% residual activity at 1 mM
SDS
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SDS inhibits activity completely at 0.01% (v/v)
sodium cholate
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1% (v/v) promotes inhibition of activity
Triton X-100
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1% (v/v) promotes inhibition of activity
Tween 60
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1% (v/v) promotes inhibition of activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CHAPS
-
0.01% (v/v) promotes small enhancement in activity
deoxycholate
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0.01% (v/v) promotes small enhancement in activity
NP-40
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0.01% (v/v) promotes small enhancement in activity
sodium cholate
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0.01% (v/v) promotes small enhancement in activity
Triton X-100
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0.01% (v/v) promotes small enhancement in activity
Tween 60
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0.01% (v/v) promotes small enhancement in activity
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004
3'-hydroxyechinenone
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in 0.4 M Tris/HCl, pH 8.0, at 30C
0.00182
3-hydroxyechinenone
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in 0.4 M Tris/HCl, pH 8.0, at 30C
0.0025
beta-carotene
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in 0.4 M Tris/HCl, pH 8.0, at 30C
0.00056
echinenone
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in 0.4 M Tris/HCl, pH 8.0, at 30C
0.001
phoenicoxanthin
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in 0.4 M Tris/HCl, pH 8.0, at 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57000
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using beta-carotene as substrate, at 30C, in dark, aerobic conditions, for 3 h, pH not specified in the publication
100000
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using canthaxanthin as substrate, in 0.4 M Tris-HCl, pH 8.0, at 30C, in dark, aerobic conditions, for 3 h, pH not specified in the publication
150000
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using beta-carotene as substrate, at 30C, in dark, aerobic conditions, for 3 h, pH not specified in the publication
467000
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using canthaxanthin as substrate, at 30C, in dark, aerobic conditions, for 3 h, pH not specified in the publication
617000
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using beta-carotene as substrate, in 0.4 M Tris-HCl, pH 8.0, at 30C, in dark, aerobic conditions, for 3 h, pH not specified in the publication
1000000
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using canthaxanthin as substrate, at 30C, in dark, aerobic conditions, for 3 h, pH not specified in the publication
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.8
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deduced from amino acid sequence
9.2
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estimated from amino acid sequence
9.4
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calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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relatively low expression in developing seeds
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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exclusively located in the cytoplasm
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22000
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SDS-PAGE
24000 - 26000
SDS-PAGE
31460
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calculated from amino acid sequene
34000
estimated from amino acid sequence; estimated from amino acid sequence
35000
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estimated from amino acid sequence
47000
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SDS-PAGE
62600
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deduced from amino acid sequence
62630
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calculated from amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
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2 * 34400, calculated from amino acid sequence
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65
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the enzyme activity disappears completely at 65C
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, phenyl Sepharose column chromatography, and hydroxyapatite column chromatography
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Q-Sepharose column chromatography, Talon nickel-affinity resin column chromatography, and Mono Q column chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in calli of Ipomoea batatas cultivar Yulmi
expressed in Escherichia coli
expressed in Escherichia coli BL21 (DE3) cells
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expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli DH10BZIP cells
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expressed in Escherichia coli DH5alpha cells
expressed in Escherichia coli JM101 cells
expressed in Escherichia coli JM109 cells
expressed in Escherichia coli JM109 cells; expressed in Escherichia coli JM109 cells
expressed in Escherichia coli strain JM101 and in Arabidopsis thaliana under the control of the seed-speciWc napin promoter from Brassica napus
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expressed in Mucor circinelloides strain MS12
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expressed in Nicotiana tabacum cultivar Nipponbare
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme down-regulation increases beta-carotene contents (38fold) and total carotenoids in transgenic plant cells and enhances their antioxidant capacity
high-light intensity leads to a transient increase in carotenoid hydroxylase mRNA level. Addition of sodium acetate and ferrous sulfate and increasing the light intensity results in a strong increase in steady-state mRNA level of the carotenoid hydroxylase after 8 h with the highest transcript level of carotenoid hydroxylase at 24 to 48 h
Haematococcus pluvialis
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high-light intensity leads to a transient increase in carotenoid hydroxylase mRNA level. Addition of sodium acetate and ferrous sulfate and increasing the light intensity results in a strong increase in steady-state mRNA level of the carotenoid hydroxylase after 8 h with the highest transcript level of carotenoid hydroxylase at 24 to 48 h; there are increased L-carotene hydroxylase mRNA steady state levels after induction of astaxanthin biosynthesis
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in the presence of 3-(3,4-dichlorophenyl)-1,1-dimethylurea, the light induction of carotenoid hydroxylase is abolished
the addition of compounds inducing reactive oxygen species like methyl viologen does not influence transcript levels of carotenoid hydroxylase. No transcript for carotenoid hydroxylase is detected after growth for 4 days under a dark/light cycle and low-light conditions
the CHX1 gene is not regulated during fruit ripening at the transcriptional level; the CHX2 gene is not regulated during fruit ripening at the transcriptional level
the DSM2 transcript level is induced (7-9fold) by drought and salt treatments and slightly induced by abscisic acid
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the DSM2 transcript level is slightly suppressed by cold stress
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there are increased L-carotene hydroxylase mRNA steady state levels after induction of astaxanthin biosynthesis
Haematococcus pluvialis
transcript levels of the beta-carotene hydroxylase gene bhy are increased to 182% during flower development
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H171A
inactive
H176A
inactive
H184A
inactive
H187A
inactive
H188A
inactive
H245A
inactive
H250A
inactive
H274A
inactive
H275A
inactive
additional information
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mutants chy1chy2lut5 and chy1chy2lut2lut5 show almost no expression of LUT5 and strongly increased expression of LUT1