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Information on EC 5.2.1.14 - beta-carotene isomerase
for references in articles please use BRENDA:EC5.2.1.14
Word Map on EC 5.2.1.14
- 5.2.1.14
- strigolactones
- rice
-
carotenoid
-
dioxygenases
- sls
- shoot
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axillary
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symbiotic
- sativa
- carlactone
-
lactones
-
outgrowth
-
terpenoid
-
arbuscular
-
carotenoid-derived
- truncatula
-
tillering
-
abscisic
- rhizobium
-
grain
-
mycorrhizal
-
legumes
- auxin
-
breakthrough
-
medicago
-
agronomic
-
enol
-
phytohormones
- ether
-
closure
-
butenolide
-
hyphal
-
rhizosphere
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
5.2.1.14
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RECOMMENDED NAME
GeneOntology No.
beta-carotene isomerase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
all-trans-beta-carotene = 9-cis-beta-carotene
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-
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all-trans-beta-carotene = 9-cis-beta-carotene
mechanism of isomerization catalysed by OsD27 involving a 1-electron transfer from the polyene p-system of beta-carotene to a [2Fe2S] cluster, generating a radical cation, which is able to rotate about the C-C single bond. Electron transfer back from the reduced [2Fe2S] cluster then generates the 9-cis-beta-carotene product. A mechanism involving single electron transfer from a [2Fe2S] cluster to form a radical anion intermediate is also possible. OsD27 retains catalytic activity under anaerobic conditions, therefore it does not require dioxygen for activity
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
beta-carotene 9-cis-all-trans isomerase
The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
additional information
the biochemical basis of the shoot branching phenotype is not due to inhibition of enzyme DWARF27, but of enzyme CCD8, EC 1.13.11.70
metabolism
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D27 is the enzyme providing the substrate for carotenoid cleavage dioxygenase 7 in the course of strigolactone biosynthesis
metabolism
biosynthesis pathway of strigolactones begins with the isomerization of all-trans-beta-carotene to 9-cis-beta-carotene catalysed by Dwarf27 (D27), strigolactone biosynthesis pathway from all-trans-beta-carotene to ent-2'-epi-5-deoxystrigol, overview
physiological function
the phenotype of d27 is correlated with enhanced polar auxin transport. The enzyme regulates rice tiller bud outgrowth
physiological function
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the enzyme is required for the regulation of axillary branching and the inhibition of secondary bud outgrowth. The enzyme is involved in strigolactone-mediated repression of shoot branching
physiological function
biosynthesis of strigolactones requires the action of enzyme Dwarf27, which catalyzes the isomerization of all-trans-beta-carotene to 9-cis-beta-carotene
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
[2Fe-2S]-center
OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Fe2+
OsD27 contains a [2Fe2S] iron-sulfur cluster that is required for catalysis
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
38% inhibition at 0.1 mM
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
33% inhibition at 0.1 mM
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
40% inhibition at 0.1 mM
3-amino-N-benzyl-N-hydroxybenzamide
7% inhibition at 0.1 mM
N-benzyl-3-chloro-N-hydroxybenzamide
21% inhibition at 0.1 mM
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
9% inhibition at 0.1 mM
N-benzyl-N-hydroxy-4-methoxybenzamide
10% inhibition at 0.1 mM
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
41% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
25% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
16% inhibition at 0.1 mM
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
40% inhibition at 0.1 mM
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
26% inhibition at 0.1 mM
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
33% inhibition at 0.1 mM
additional information
OsD27 is not inhibited by hydroxamic acids that cause shoot branching in planta, but OsD27 is partially inhibited by terpene-like hydroxamic acids. Compounds D2, D4, D5 and D6 that show a shoot branching phenotype in planta give no inhibition at all. No inhibition by N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide, N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide, 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide, 2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide, N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide, N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide, 3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide, N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide, (2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide, 3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide, (2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide, N-hydroxy-3-(4-methoxyphenyl)propanamide, (2E,4E)-N-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienamide, and abamine
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene DWARF27, recombinant expression in Escherichia coli strain BL21
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LINKS TO OTHER DATABASES (specific for EC-Number 5.2.1.14)
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