Information on EC 1.13.11.69 - carlactone synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.69
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RECOMMENDED NAME
GeneOntology No.
carlactone synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
9-cis-10'-apo-beta-carotenal + 2 O2 = carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
5-deoxystrigol biosynthesis
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Carotenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
9-cis-10'-apo-beta-carotenal:O2 oxidoreductase (14,15-cleaving, carlactone-forming)
Requires Fe2+. The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza. Also catalyses EC 1.13.11.70, all-trans-10'-apo-beta-carotenal 13,14-cleaving dioxygenase, but 10-fold slower.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 (EC 1.13.11.68) and CCD8, which act sequentially on 9-cis-beta-carotene, strigolactone biosynthesis pathway from all-trans-beta-carotene to ent-2'-epi-5-deoxystrigol, overview
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-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
show the reaction diagram
all-trans-10'-apo-beta-carotenal + O2
13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
show the reaction diagram
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-
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?
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
9-cis-10'-apo-beta-carotenal + 2 O2
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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involved in catalysis, mechanism overview
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
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over 95% inhibition at 0.1 mM
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
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52% inhibition at 0.1 mM
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
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over 95% inhibition at 0.1 mM
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
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47% inhibition at 0.1 mM
(2E,4E)-N-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienamide
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over 95% inhibition at 0.1 mM
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
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over 95% inhibition at 0.1 mM
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
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over 95% inhibition at 0.1 mM
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
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over 95% inhibition at 0.1 mM
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
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78% inhibition at 0.1 mM
3-amino-N-benzyl-N-hydroxybenzamide
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over 95% inhibition at 0.1 mM
abamine
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over 95% inhibition at 0.1 mM
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
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over 95% inhibition at 0.1 mM
N-benzyl-3-chloro-N-hydroxybenzamide
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over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
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over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
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over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
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over 95% inhibition at 0.1 mM
N-benzyl-N-hydroxy-4-methoxybenzamide
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over 95% inhibition at 0.1 mM
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
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over 95% inhibition at 0.1 mM
N-hydroxy-3-(4-methoxyphenyl)propanamide
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over 95% inhibition at 0.1 mM
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
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70% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
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over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
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over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
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over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
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over 95% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
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over 95% inhibition at 0.1 mM
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
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sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
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47% inhibition at 0.1 mM
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
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92% inhibition at 0.1 mM
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
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two-step kinetic mechanism, pre-steady-state kinetic analysis
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9
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activity range, profile overview
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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expression of gene is widely distributed, but at low level
Manually annotated by BRENDA team
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene ccd8, recombinant expression of N-terminally His6-tagged AtCCD8 lacking the first 168 bp, corresponding to a chloroplast transit peptide, in Escherichia coli strain BL21
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme is upregulated in the root eleongation zone following 24 h auxin treatment, and hypocotyl, and this is not required for the inhibition of shoot branching
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expression is induced by auxin
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gene is repressed by low phosphate stress
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no evidence is found for auxin-induced upregulation of enzyme expression in nodal tissue
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information