BRENDA - Enzyme Database

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)
EC Number
Commentary
Organism
1.13.11.68
gene ccd7, recombinant expression of GST-tagged AtCCD7 in Escherichia coli
Arabidopsis thaliana
1.13.11.69
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
1.13.11.70
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
5.2.1.14
expression in Escherichia coli; gene DWARF27, recombinant expression in Escherichia coli strain BL21
Oryza sativa Japonica Group
Inhibitors
EC Number
Inhibitors
Commentary
Organism
Structure
1.13.11.68
additional information
no inhibition by hydroxamic acids
Arabidopsis thaliana
1.13.11.69
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(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
1.13.11.69
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
abamine
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
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
1.13.11.69
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
-
Arabidopsis thaliana
1.13.11.69
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(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
1.13.11.70
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
abamine
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
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
1.13.11.70
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
-
Arabidopsis thaliana
1.13.11.70
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
Arabidopsis thaliana
5.2.1.14
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
38% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
3-amino-N-benzyl-N-hydroxybenzamide
7% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
additional information
enzyme is not inhibited by hydroxamic acids that cause shoot branching in planta, but D27 is partially inhibited by terpene-like hydroxamic acids; 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
Oryza sativa Japonica Group
5.2.1.14
N-benzyl-3-chloro-N-hydroxybenzamide
21% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
9% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-benzyl-N-hydroxy-4-methoxybenzamide
10% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
41% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
25% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
16% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
silver acetate
-
Oryza sativa Japonica Group
5.2.1.14
silver(I) acetate
inactivation
Oryza sativa Japonica Group
5.2.1.14
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
26% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
KM Value [mM]
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.13.11.69
additional information
-
additional information
two-step kinetic mechanism, pre-steady-state kinetic analysis
Arabidopsis thaliana
1.13.11.70
additional information
-
additional information
two-step kinetic mechanism, pre-steady-state kinetic analysis
Arabidopsis thaliana
5.2.1.14
0.00026
-
9-cis-beta-carotene
pH 6.4, 25°C
Oryza sativa Japonica Group
Metals/Ions
EC Number
Metals/Ions
Commentary
Organism
Structure
5.2.1.14
Fe2+
OsD27 contains a [2Fe2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
5.2.1.14
Iron
presence of an iron-sulfur cluster involved in catalysis
Oryza sativa Japonica Group
Natural Substrates/ Products (Substrates)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1.13.11.68
9-cis-beta-carotene + O2
Arabidopsis thaliana
-
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
?
1.13.11.69
9-cis-10'-apo-beta-carotenal + 2 O2
Arabidopsis thaliana
-
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
?
1.13.11.70
all-trans-10'-apo-beta-carotenal + O2
Arabidopsis thaliana
-
13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
-
-
?
5.2.1.14
all-trans-beta-carotene
Oryza sativa Japonica Group
-
9-cis-beta-carotene
-
-
?
Organism
EC Number
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
1.13.11.68
Arabidopsis thaliana
Q7XJM2
-
-
1.13.11.69
Arabidopsis thaliana
Q8VY26
-
-
1.13.11.70
Arabidopsis thaliana
Q8VY26
-
-
5.2.1.14
Oryza sativa Japonica Group
C7AU21
-
-
Purification (Commentary)
EC Number
Commentary
Organism
1.13.11.68
recombinant GST-tagged AtCCD7 from Escherichia coli by glutathione affinity chromatographyy
Arabidopsis thaliana
1.13.11.69
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
Arabidopsis thaliana
1.13.11.70
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
Arabidopsis thaliana
5.2.1.14
recombinant enzyme from Escherichia coli strain BL21
Oryza sativa Japonica Group
Reaction
EC Number
Reaction
Commentary
Organism
1.13.11.69
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
1.13.11.70
all-trans-10'-apo-beta-carotenal + O2 = 13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
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
5.2.1.14
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
Oryza sativa Japonica Group
Substrates and Products (Substrate)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.13.11.68
9-cis-beta-carotene + O2
-
744876
Arabidopsis thaliana
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
?
1.13.11.68
9-cis-beta-carotene + O2
AtCCD7 preferentially cleaves 9-cis-beta-carotene
744876
Arabidopsis thaliana
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
?
1.13.11.69
9-cis-10'-apo-beta-carotenal + 2 O2
-
744876
Arabidopsis thaliana
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
1.13.11.69
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
-
-
-
?
1.13.11.69
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
?
-
-
-
-
1.13.11.70
all-trans-10'-apo-beta-carotenal + O2
-
744876
Arabidopsis thaliana
13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
-
-
-
?
1.13.11.70
additional information
CCD8-dependent conversion of beta-apo-10beta-carotenal to unstable carlactone, reaction of EC 1.13.11.69
744876
Arabidopsis thaliana
?
-
-
-
-
5.2.1.14
9-cis-beta-carotene
-
744876
Oryza sativa Japonica Group
all-trans-beta-carotene
-
-
-
r
5.2.1.14
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
?
5.2.1.14
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
r
5.2.1.14
additional information
catalytic mechanism involves a 1-electron transfer from the polyene pi-system of beta-carotene to a [2Fe-2S] cluster, generating a radical cation, which is able to rotate about the C-C single bond. Electron transfer back from the reduced [2Fe-2S] cluster would then generate the 9-cis-beta-carotene product. A mechanism involving single electron transfer from a [2Fe-2S] cluster to form a radical anion intermediate is also possible
744876
Oryza sativa Japonica Group
?
-
-
-
-
Temperature Optimum [°C]
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
1.13.11.68
25
-
assay at
Arabidopsis thaliana
1.13.11.69
25
-
assay at
Arabidopsis thaliana
1.13.11.70
25
-
assay at
Arabidopsis thaliana
5.2.1.14
25
-
assay at
Oryza sativa Japonica Group
pH Optimum
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
1.13.11.68
7.8
-
assay at
Arabidopsis thaliana
1.13.11.69
6
-
-
Arabidopsis thaliana
5.2.1.14
6.5
-
-
Oryza sativa Japonica Group
pH Range
EC Number
pH Minimum
pH Maximum
Commentary
Organism
1.13.11.69
5.5
9
activity range, profile overview
Arabidopsis thaliana
5.2.1.14
4
10.2
broad pH spectrum, profile overview
Oryza sativa Japonica Group
Cofactor
EC Number
Cofactor
Commentary
Organism
Structure
5.2.1.14
[2Fe-2S]-center
; OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
Cloned(Commentary) (protein specific)
EC Number
Commentary
Organism
1.13.11.68
gene ccd7, recombinant expression of GST-tagged AtCCD7 in Escherichia coli
Arabidopsis thaliana
1.13.11.69
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
1.13.11.70
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
5.2.1.14
expression in Escherichia coli; gene DWARF27, recombinant expression in Escherichia coli strain BL21
Oryza sativa Japonica Group
Cofactor (protein specific)
EC Number
Cofactor
Commentary
Organism
Structure
5.2.1.14
[2Fe-2S]-center
; OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
Inhibitors (protein specific)
EC Number
Inhibitors
Commentary
Organism
Structure
1.13.11.68
additional information
no inhibition by hydroxamic acids
Arabidopsis thaliana
1.13.11.69
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
(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
1.13.11.69
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
abamine
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
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
1.13.11.69
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
-
Arabidopsis thaliana
1.13.11.69
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.69
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E)-3-(3,4-dimethoxyphenyl)-N-hydroxyprop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
52% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E)-N-hydroxy-3-(4-methoxyphenyl)prop-2-enamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
(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
1.13.11.70
2-(2H-1,3-benzodioxol-5-yl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
2-(3,4-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
3-(3,4-dimethoxyphenyl)-N-hydroxy-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
78% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
3-amino-N-benzyl-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
abamine
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
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
1.13.11.70
N-benzyl-2-(3,4-dimethoxyphenyl)-N-hydroxyacetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-3-chloro-N-hydroxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-benzyl-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-hydroxy-3-(4-methoxyphenyl)-N-octylpropanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
70% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-hydroxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-3-(4-methoxyphenyl)propanamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
over 95% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
-
Arabidopsis thaliana
1.13.11.70
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
47% inhibition at 0.1 mM
Arabidopsis thaliana
1.13.11.70
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
92% inhibition at 0.1 mM
Arabidopsis thaliana
5.2.1.14
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
38% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
3-amino-N-benzyl-N-hydroxybenzamide
7% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
additional information
enzyme is not inhibited by hydroxamic acids that cause shoot branching in planta, but D27 is partially inhibited by terpene-like hydroxamic acids; 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
Oryza sativa Japonica Group
5.2.1.14
N-benzyl-3-chloro-N-hydroxybenzamide
21% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
9% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-benzyl-N-hydroxy-4-methoxybenzamide
10% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
41% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
25% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
16% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
silver acetate
-
Oryza sativa Japonica Group
5.2.1.14
silver(I) acetate
inactivation
Oryza sativa Japonica Group
5.2.1.14
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
26% inhibition at 0.1 mM
Oryza sativa Japonica Group
5.2.1.14
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
KM Value [mM] (protein specific)
EC Number
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
1.13.11.69
additional information
-
additional information
two-step kinetic mechanism, pre-steady-state kinetic analysis
Arabidopsis thaliana
1.13.11.70
additional information
-
additional information
two-step kinetic mechanism, pre-steady-state kinetic analysis
Arabidopsis thaliana
5.2.1.14
0.00026
-
9-cis-beta-carotene
pH 6.4, 25°C
Oryza sativa Japonica Group
Metals/Ions (protein specific)
EC Number
Metals/Ions
Commentary
Organism
Structure
5.2.1.14
Fe2+
OsD27 contains a [2Fe2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
5.2.1.14
Iron
presence of an iron-sulfur cluster involved in catalysis
Oryza sativa Japonica Group
Natural Substrates/ Products (Substrates) (protein specific)
EC Number
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
1.13.11.68
9-cis-beta-carotene + O2
Arabidopsis thaliana
-
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
?
1.13.11.69
9-cis-10'-apo-beta-carotenal + 2 O2
Arabidopsis thaliana
-
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
?
1.13.11.70
all-trans-10'-apo-beta-carotenal + O2
Arabidopsis thaliana
-
13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
-
-
?
5.2.1.14
all-trans-beta-carotene
Oryza sativa Japonica Group
-
9-cis-beta-carotene
-
-
?
Purification (Commentary) (protein specific)
EC Number
Commentary
Organism
1.13.11.68
recombinant GST-tagged AtCCD7 from Escherichia coli by glutathione affinity chromatographyy
Arabidopsis thaliana
1.13.11.69
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
Arabidopsis thaliana
1.13.11.70
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography
Arabidopsis thaliana
5.2.1.14
recombinant enzyme from Escherichia coli strain BL21
Oryza sativa Japonica Group
Substrates and Products (Substrate) (protein specific)
EC Number
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
1.13.11.68
9-cis-beta-carotene + O2
-
744876
Arabidopsis thaliana
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
?
1.13.11.68
9-cis-beta-carotene + O2
AtCCD7 preferentially cleaves 9-cis-beta-carotene
744876
Arabidopsis thaliana
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
?
1.13.11.69
9-cis-10'-apo-beta-carotenal + 2 O2
-
744876
Arabidopsis thaliana
carlactone + (2E,4E,6E)-7-hydroxy-4-methylhepta-2,4,6-trienal
-
-
-
?
1.13.11.69
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
-
-
-
?
1.13.11.69
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
?
-
-
-
-
1.13.11.70
all-trans-10'-apo-beta-carotenal + O2
-
744876
Arabidopsis thaliana
13-apo-beta-carotenone + (2E,4E,6E)-4-methylocta-2,4,6-trienedial
-
-
-
?
1.13.11.70
additional information
CCD8-dependent conversion of beta-apo-10beta-carotenal to unstable carlactone, reaction of EC 1.13.11.69
744876
Arabidopsis thaliana
?
-
-
-
-
5.2.1.14
9-cis-beta-carotene
-
744876
Oryza sativa Japonica Group
all-trans-beta-carotene
-
-
-
r
5.2.1.14
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
?
5.2.1.14
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
r
5.2.1.14
additional information
catalytic mechanism involves a 1-electron transfer from the polyene pi-system of beta-carotene to a [2Fe-2S] cluster, generating a radical cation, which is able to rotate about the C-C single bond. Electron transfer back from the reduced [2Fe-2S] cluster would then generate the 9-cis-beta-carotene product. A mechanism involving single electron transfer from a [2Fe-2S] cluster to form a radical anion intermediate is also possible
744876
Oryza sativa Japonica Group
?
-
-
-
-
Temperature Optimum [°C] (protein specific)
EC Number
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
1.13.11.68
25
-
assay at
Arabidopsis thaliana
1.13.11.69
25
-
assay at
Arabidopsis thaliana
1.13.11.70
25
-
assay at
Arabidopsis thaliana
5.2.1.14
25
-
assay at
Oryza sativa Japonica Group
pH Optimum (protein specific)
EC Number
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
1.13.11.68
7.8
-
assay at
Arabidopsis thaliana
1.13.11.69
6
-
-
Arabidopsis thaliana
5.2.1.14
6.5
-
-
Oryza sativa Japonica Group
pH Range (protein specific)
EC Number
pH Minimum
pH Maximum
Commentary
Organism
1.13.11.69
5.5
9
activity range, profile overview
Arabidopsis thaliana
5.2.1.14
4
10.2
broad pH spectrum, profile overview
Oryza sativa Japonica Group
General Information
EC Number
General Information
Commentary
Organism
1.13.11.68
metabolism
biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 and CCD8 (EC 1.13.11.70), which act sequentially on 9-cis-beta-carotene, strigolactone biosynthesis pathway from all-trans-beta-carotene to ent-2'-epi-5-deoxystrigol
Arabidopsis thaliana
1.13.11.68
additional information
the biochemical basis of the shoot branching phenotype is not due to inhibition of enzyme CCD7, but of enzyme CCD8, EC 1.13.11.70
Arabidopsis thaliana
1.13.11.68
physiological function
biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 and CCD8 (EC 1.13.11.70), which act sequentially on 9-cis-beta-carotene
Arabidopsis thaliana
1.13.11.69
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
Arabidopsis thaliana
1.13.11.69
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
1.13.11.69
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
1.13.11.70
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
Arabidopsis thaliana
1.13.11.70
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
1.13.11.70
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
5.2.1.14
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
Oryza sativa Japonica Group
5.2.1.14
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
Oryza sativa Japonica Group
5.2.1.14
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
Oryza sativa Japonica Group
General Information (protein specific)
EC Number
General Information
Commentary
Organism
1.13.11.68
metabolism
biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 and CCD8 (EC 1.13.11.70), which act sequentially on 9-cis-beta-carotene, strigolactone biosynthesis pathway from all-trans-beta-carotene to ent-2'-epi-5-deoxystrigol
Arabidopsis thaliana
1.13.11.68
additional information
the biochemical basis of the shoot branching phenotype is not due to inhibition of enzyme CCD7, but of enzyme CCD8, EC 1.13.11.70
Arabidopsis thaliana
1.13.11.68
physiological function
biosynthesis of strigolactones requires the action of two CCD enzymes, CCD7 and CCD8 (EC 1.13.11.70), which act sequentially on 9-cis-beta-carotene
Arabidopsis thaliana
1.13.11.69
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
Arabidopsis thaliana
1.13.11.69
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
1.13.11.69
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
1.13.11.70
malfunction
the biochemical basis of the shoot branching phenotype is due to inhibition of enzyme CCD8
Arabidopsis thaliana
1.13.11.70
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
1.13.11.70
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
5.2.1.14
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
Oryza sativa Japonica Group
5.2.1.14
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
Oryza sativa Japonica Group
5.2.1.14
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
Oryza sativa Japonica Group