BRENDA - Enzyme Database
show all sequences of 5.2.1.14

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)
Commentary
Organism
expression in Escherichia coli; gene DWARF27, recombinant expression in Escherichia coli strain BL21
Oryza sativa Japonica Group
Inhibitors
Inhibitors
Commentary
Organism
Structure
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
38% inhibition at 0.1 mM
Oryza sativa Japonica Group
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
3-amino-N-benzyl-N-hydroxybenzamide
7% inhibition at 0.1 mM
Oryza sativa Japonica Group
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
N-benzyl-3-chloro-N-hydroxybenzamide
21% inhibition at 0.1 mM
Oryza sativa Japonica Group
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
9% inhibition at 0.1 mM
Oryza sativa Japonica Group
N-benzyl-N-hydroxy-4-methoxybenzamide
10% inhibition at 0.1 mM
Oryza sativa Japonica Group
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
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
25% inhibition at 0.1 mM
Oryza sativa Japonica Group
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
16% inhibition at 0.1 mM
Oryza sativa Japonica Group
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
silver acetate
-
Oryza sativa Japonica Group
silver(I) acetate
inactivation
Oryza sativa Japonica Group
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
26% inhibition at 0.1 mM
Oryza sativa Japonica Group
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00026
-
9-cis-beta-carotene
pH 6.4, 25°C
Oryza sativa Japonica Group
Metals/Ions
Metals/Ions
Commentary
Organism
Structure
Fe2+
OsD27 contains a [2Fe2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
Iron
presence of an iron-sulfur cluster involved in catalysis
Oryza sativa Japonica Group
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
all-trans-beta-carotene
Oryza sativa Japonica Group
-
9-cis-beta-carotene
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Oryza sativa Japonica Group
C7AU21
-
-
Purification (Commentary)
Commentary
Organism
recombinant enzyme from Escherichia coli strain BL21
Oryza sativa Japonica Group
Reaction
Reaction
Commentary
Organism
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)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
9-cis-beta-carotene
-
744876
Oryza sativa Japonica Group
all-trans-beta-carotene
-
-
-
r
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
?
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
r
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]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Oryza sativa Japonica Group
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
-
-
Oryza sativa Japonica Group
pH Range
pH Minimum
pH Maximum
Commentary
Organism
4
10.2
broad pH spectrum, profile overview
Oryza sativa Japonica Group
Cofactor
Cofactor
Commentary
Organism
Structure
[2Fe-2S]-center
; OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
Cloned(Commentary) (protein specific)
Commentary
Organism
expression in Escherichia coli; gene DWARF27, recombinant expression in Escherichia coli strain BL21
Oryza sativa Japonica Group
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
[2Fe-2S]-center
; OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
38% inhibition at 0.1 mM
Oryza sativa Japonica Group
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
3-amino-N-benzyl-N-hydroxybenzamide
7% inhibition at 0.1 mM
Oryza sativa Japonica Group
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
N-benzyl-3-chloro-N-hydroxybenzamide
21% inhibition at 0.1 mM
Oryza sativa Japonica Group
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
9% inhibition at 0.1 mM
Oryza sativa Japonica Group
N-benzyl-N-hydroxy-4-methoxybenzamide
10% inhibition at 0.1 mM
Oryza sativa Japonica Group
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
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
25% inhibition at 0.1 mM
Oryza sativa Japonica Group
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
16% inhibition at 0.1 mM
Oryza sativa Japonica Group
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
40% inhibition at 0.1 mM
Oryza sativa Japonica Group
silver acetate
-
Oryza sativa Japonica Group
silver(I) acetate
inactivation
Oryza sativa Japonica Group
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
26% inhibition at 0.1 mM
Oryza sativa Japonica Group
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
33% inhibition at 0.1 mM
Oryza sativa Japonica Group
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.00026
-
9-cis-beta-carotene
pH 6.4, 25°C
Oryza sativa Japonica Group
Metals/Ions (protein specific)
Metals/Ions
Commentary
Organism
Structure
Fe2+
OsD27 contains a [2Fe2S] iron-sulfur cluster that is required for catalysis
Oryza sativa Japonica Group
Iron
presence of an iron-sulfur cluster involved in catalysis
Oryza sativa Japonica Group
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
all-trans-beta-carotene
Oryza sativa Japonica Group
-
9-cis-beta-carotene
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant enzyme from Escherichia coli strain BL21
Oryza sativa Japonica Group
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
9-cis-beta-carotene
-
744876
Oryza sativa Japonica Group
all-trans-beta-carotene
-
-
-
r
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
?
all-trans-beta-carotene
-
744876
Oryza sativa Japonica Group
9-cis-beta-carotene
-
-
-
r
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)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Oryza sativa Japonica Group
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
6.5
-
-
Oryza sativa Japonica Group
pH Range (protein specific)
pH Minimum
pH Maximum
Commentary
Organism
4
10.2
broad pH spectrum, profile overview
Oryza sativa Japonica Group
General Information
General Information
Commentary
Organism
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
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
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)
General Information
Commentary
Organism
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
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
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
Other publictions for EC 5.2.1.14
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
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)
749033
Bruno
On the substrate specificity ...
Oryza sativa Japonica Group
Planta
243
1429-1440
2016
1
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1
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3
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1
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5
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1
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744876
Harrison
Biochemical characterization ...
Oryza sativa Japonica Group
FEBS J.
282
3986-4000
2015
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1
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16
1
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2
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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
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16
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4
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1
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1
1
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3
3
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747424
van Zeijl
The strigolactone biosynthesi ...
Medicago truncatula
BMC Plant Biol.
15
260
2015
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-
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1
1
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1
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720749
Waters
The Arabidopsis ortholog of ri ...
Arabidopsis thaliana
Plant Physiol.
159
1073-1085
2012
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1
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721057
Alder
The path from beta-carotene to ...
Oryza sativa
Science
335
1348-1351
2012
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1
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1
1
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720674
Lin
DWARF27, an iron-containing pr ...
Oryza sativa
Plant Cell
21
1512-1525
2009
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2
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