Information on EC 1.13.11.65 - carotenoid isomerooxygenase

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

EC NUMBER
COMMENTARY hide
1.13.11.65
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RECOMMENDED NAME
GeneOntology No.
carotenoid isomerooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
zeaxanthin + O2 = (3R)-11-cis-3-hydroxyretinal + (3R)-all-trans-3-hydroxyretinal
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
11-cis-3-hydroxyretinal biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
zeaxanthin:oxygen 15,15'-oxidoreductase (bond-cleaving, cis-isomerizing)
The enzyme, characterized from the moth Galleria mellonella and the fruit fly Drosophila melanogaster, is involved in the synthesis of retinal from dietary caroteoids in insects. The enzyme accepts different all-trans carotenoids, including beta-carotene, alpha-carotene and lutein, and catalyses the symmetrical cleavage of the carotenoid and the simultaneous isomerization of only one of the products to a cis configuration. When the substrate is hydroxylated only in one side (as in cryptoxanthin), the enzyme preferentially isomerizes the hydroxylated part of the molecule.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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mutants show no photophobic behavior indicating that NinaB is essential for larval light perception. Enzyme expression and chromophore production is governed by eyeless and so, major control genes for eye development
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-hydroxy-beta-apo-10'-carotenal + O2
3-hydroxy-beta-apo-13-carotenone + 3-hydroxy-beta-apo-15-carotenal
show the reaction diagram
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plus a minor product presumably representing 3-hydroxy-beta-apo-11-carotenal
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?
3-hydroxy-beta-apo-8'-carotenal + O2
?
show the reaction diagram
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-
-
?
alpha-carotene + O2
?
show the reaction diagram
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-
-
?
apo-8'-carotenal + O2
?
show the reaction diagram
astaxanthin + O2
?
show the reaction diagram
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single cleavage site at the 13'/14' double bond
-
?
beta,beta-carotene + O2
all-trans-retinal + 11-cis-retinal
show the reaction diagram
beta-apo-10'-carotenal + O2
beta-apo-13-carotenone
show the reaction diagram
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plus minor amounts of beta-apo-15-carotenal
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?
beta-apo-8'-carotenal + O2
beta-apo-13-carotenone + retinal
show the reaction diagram
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-
-
?
beta-carotene + O2
retinal + beta-apo-14'-carotenal + beta-apo-13-carotenone
show the reaction diagram
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-
-
?
canthaxanthin + O2
?
show the reaction diagram
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two cleavage sites at the 11'/12' or 13'/14' double bond
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?
cryptoxanthin + O2
11-cis-3-hydroxyretinal + 11-cis-retinal
show the reaction diagram
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11-cis-3-hydroxyretinal and 11-cis-retinal exist in a molar ratio of 8:1, indicating that the enzyme preferentially isomerizes the half site of cryptoxanthin with the hydroxylated beta-ionone ring
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?
decaprenoxanthin + O2
?
show the reaction diagram
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?
dihydroxylycopene + O2
?
show the reaction diagram
hydroxylycopene + O2
?
show the reaction diagram
lutein + O2
?
show the reaction diagram
lycopene + O2
?
show the reaction diagram
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-
-
?
nostoxanthin + O2
?
show the reaction diagram
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two cleavage sites at the 11'/12' or 13'/14' double bond
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?
sarcinaxanthin + O2
?
show the reaction diagram
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-
-
-
?
sarprenoxanthin + O2
?
show the reaction diagram
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-
?
zeaxanthin + O2
(3R)-11-cis-3-hydroxyretinal + (3R)-all-trans-3-hydroxyretinal
show the reaction diagram
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beta-carotene is first converted to zeaxanthin and then cleaved by the enzmye to directly yield 3-hydroxy-retinal
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?
zeaxanthin + O2
(3R)-all-trans-3-hydroxyretinal + (3R)-11-cis-3-hydroxyretinal
show the reaction diagram
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?
zeaxanthin + O2
?
show the reaction diagram
additional information
?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0438
3-hydroxy-beta-apo-10'-carotenal
pH 7.8, 28°C
0.0219
3-hydroxy-beta-apo-8'-carotenal
pH 7.8, 28°C
0.0221
alpha-carotene
pH 6.8, 20°C
0.1229
apo-8'-carotenal
0.0104
beta,beta-carotene
pH 6.8, 20°C
0.0294
beta-apo-10'-carotenal
pH 7.8, 28°C
0.0041
beta-apo-8'-carotenal
pH 7.8, 28°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
764.3
3-hydroxy-beta-apo-10'-carotenal
Mycobacterium tuberculosis
P9WPR5
pH 7.8, 28°C
1308
3-hydroxy-beta-apo-8'-carotenal
Mycobacterium tuberculosis
P9WPR5
pH 7.8, 28°C
0.0082
alpha-carotene
Galleria mellonella
A8Y9I2
pH 6.8, 20°C
4.9
apo-8'-carotenal
0.0087
beta,beta-carotene
Galleria mellonella
A8Y9I2
pH 6.8, 20°C
561.7
beta-apo-10'-carotenal
Mycobacterium tuberculosis
P9WPR5
pH 7.8, 28°C
392.7
beta-apo-8'-carotenal
Mycobacterium tuberculosis
P9WPR5
pH 7.8, 28°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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gene expression is eye-dependent and is activated as adownstream target of the eyeless/pax6 and sine oculis master control genes for eye development
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
gene expression is eye-dependent and is activated as a downstream target of the eyeless/pax6 and sine oculis master control genes for eye development
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