BRENDA - Enzyme Database
show all sequences of 1.13.11.69

Biochemical characterization and selective inhibition of beta-carotene cis-trans isomerase D27 and carotenoid cleavage dioxygenase CCD8 on the strigolactone biosynthetic pathway

Harrison, P.J.; Newgas, S.A.; Descombes, F.; Shepherd, S.A.; Thompson, A.J.; Bugg, T.D.; FEBS J. 282, 3986-4000 (2015)

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
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
Arabidopsis thaliana
Inhibitors
Inhibitors
Commentary
Organism
Structure
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
Arabidopsis thaliana
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
Arabidopsis thaliana
(2E,4E)-N-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
Arabidopsis thaliana
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
abamine
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
additional information
AtCCD8 is inhibited in a time-dependent fashion by hydroxamic acids 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 and 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide with over 95% inhibition at 0.10 mM, hydroxamic acids acids 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 and 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide cause a shoot branching phenotype in Arabidopsis thaliana. Selective inhibition of CCD8 is observed using hydroxamic acids N-hydroxy-3-(4-methoxyphenyl)propanamide and N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide. No inhibition by N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
Arabidopsis thaliana
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
-
Arabidopsis thaliana
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
Arabidopsis thaliana
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
Arabidopsis thaliana
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
two-step kinetic mechanism, pre-steady-state kinetic analysis
Arabidopsis thaliana
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
9-cis-10'-apo-beta-carotenal + 2 O2
Arabidopsis thaliana
-
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Arabidopsis thaliana
Q8VY26
-
-
Purification (Commentary)
Purification (Commentary)
Organism
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
Arabidopsis thaliana
Reaction
Reaction
Commentary
Organism
Reaction ID
9-cis-10'-apo-beta-carotenal + 2 O2 = carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
acid-base catalysis in the CCD8 catalytic cycle and existence of an essential cysteine residue in the CCD8 active site, two-step kinetic mechanism
Arabidopsis thaliana
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
9-cis-10'-apo-beta-carotenal + 2 O2
-
744876
Arabidopsis thaliana
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
CCD8-dependent conversion of beta-apo-10'-carotenal to unstable carlactone
744876
Arabidopsis thaliana
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
additional information
CCD8-dependent conversion of all-trans-10'-apo-beta-carotenal to 13-apo-beta-carotenone, reaction of EC 1.13.11.70
744876
Arabidopsis thaliana
?
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
carotenoid cleavage dioxygenase
-
Arabidopsis thaliana
CCD8
-
Arabidopsis thaliana
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Arabidopsis thaliana
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6
-
-
Arabidopsis thaliana
pH Range
pH Minimum
pH Maximum
Commentary
Organism
5.5
9
activity range, profile overview
Arabidopsis thaliana
Cloned(Commentary) (protein specific)
Commentary
Organism
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
Arabidopsis thaliana
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
Arabidopsis thaliana
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
Arabidopsis thaliana
(2E,4E)-N-hydroxy-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
Arabidopsis thaliana
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
abamine
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
additional information
AtCCD8 is inhibited in a time-dependent fashion by hydroxamic acids 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 and 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide with over 95% inhibition at 0.10 mM, hydroxamic acids acids 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 and 2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide cause a shoot branching phenotype in Arabidopsis thaliana. Selective inhibition of CCD8 is observed using hydroxamic acids N-hydroxy-3-(4-methoxyphenyl)propanamide and N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide. No inhibition by N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
Arabidopsis thaliana
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
-
Arabidopsis thaliana
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
Arabidopsis thaliana
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
Arabidopsis thaliana
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
two-step kinetic mechanism, pre-steady-state kinetic analysis
Arabidopsis thaliana
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
9-cis-10'-apo-beta-carotenal + 2 O2
Arabidopsis thaliana
-
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
Arabidopsis thaliana
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
9-cis-10'-apo-beta-carotenal + 2 O2
-
744876
Arabidopsis thaliana
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
9-cis-10'-apo-beta-carotenal + 2 O2
CCD8-dependent conversion of beta-apo-10'-carotenal to unstable carlactone
744876
Arabidopsis thaliana
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
additional information
CCD8-dependent conversion of all-trans-10'-apo-beta-carotenal to 13-apo-beta-carotenone, reaction of EC 1.13.11.70
744876
Arabidopsis thaliana
?
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Arabidopsis thaliana
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6
-
-
Arabidopsis thaliana
pH Range (protein specific)
pH Minimum
pH Maximum
Commentary
Organism
5.5
9
activity range, profile overview
Arabidopsis thaliana
General Information
General Information
Commentary
Organism
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
Arabidopsis thaliana
metabolism
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
Arabidopsis thaliana
physiological function
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
Arabidopsis thaliana
General Information (protein specific)
General Information
Commentary
Organism
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
Arabidopsis thaliana
metabolism
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
Arabidopsis thaliana
physiological function
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
Arabidopsis thaliana
Other publictions for EC 1.13.11.69
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
744912
Bruno
Insights into the formation o ...
Pisum sativum
FEBS Lett.
591
792-800
2017
-
-
-
-
-
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1
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1
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1
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1
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3
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1
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1
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1
1
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744876
Harrison
Biochemical characterization ...
Arabidopsis thaliana
FEBS J.
282
3986-4000
2015
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1
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29
1
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1
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1
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1
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1
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1
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29
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1
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1
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3
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1
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1
1
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3
3
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720753
Guan
Diverse roles of strigolactone ...
Zea mays
Plant Physiol.
160
1303-1317
2012
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1
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1
1
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721057
Alder
The path from beta-carotene to ...
Pisum sativum, Arabidopsis thaliana
Science
335
1348-1351
2012
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728380
Kohlen
The tomato CAROTENOID CLEAVAGE ...
Solanum lycopersicum
New Phytol.
196
535-547
2012
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6
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1
1
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718523
Jiang
-
MAX4 gene is involved in the r ...
Arabidopsis thaliana
Acta Physiol. Plant.
33
867-875
2011
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1
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1
1
1
1
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720559
Ledger
Modified CAROTENOID CLEAVAGE D ...
Actinidia chinensis
New Phytol.
188
803-813
2010
-
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1
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1
1
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720702
Auldridge
Characterization of three memb ...
Arabidopsis thaliana
Plant J.
45
982-993
2006
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Bainbridge
Hormonally controlled expressi ...
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2005
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719823
Schwartz
The biochemical characterizati ...
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2004
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MAX4 and RMS1 are orthologous ...
Arabidopsis thaliana
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