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Literature summary for 5.2.1.14 extracted from

  • Harrison, P.J.; Newgas, S.A.; Descombes, F.; Shepherd, S.A.; Thompson, A.J.; Bugg, T.D.
    Biochemical characterization and selective inhibition of beta-carotene cis-trans isomerase D27 and carotenoid cleavage dioxygenase CCD8 on the strigolactone biosynthetic pathway (2015), FEBS J., 282, 3986-4000 .
    View publication on PubMed
Search for more literature for 5.2.1.14

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Oryza sativa Japonica Group
gene DWARF27, recombinant expression in Escherichia coli strain BL21 Oryza sativa Japonica Group

Inhibitors

Inhibitors Comment 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 Comment Organism Structure
0.00026
-
 9-cis-beta-carotene pH 6.4, 25°C Oryza sativa Japonica Group

Metals/Ions

Metals/Ions Comment 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 Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
all-trans-beta-carotene Oryza sativa Japonica Group
-
 9-cis-beta-carotene
-
 ?

Organism

Organism UniProt Comment Textmining
Oryza sativa Japonica Group C7AU21
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzyme from Escherichia coli strain BL21 Oryza sativa Japonica Group

Reaction

Reaction Comment Organism Reaction ID
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
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
9-cis-beta-carotene
-
 Oryza sativa Japonica Group all-trans-beta-carotene
-
 r
all-trans-beta-carotene
-
 Oryza sativa Japonica Group 9-cis-beta-carotene
-
 ?
all-trans-beta-carotene
-
 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 Oryza sativa Japonica Group ?
-
 ?

Synonyms

Synonyms Comment Organism
beta-carotene cis–trans isomerase
-
 Oryza sativa Japonica Group
D27
-
 Oryza sativa Japonica Group
DWARF27
-
 Oryza sativa Japonica Group
OsD27
-
 Oryza sativa Japonica Group

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Oryza sativa Japonica Group

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
-
 Oryza sativa Japonica Group

pH Range

pH Minimum pH Maximum Comment Organism
4 10.2 broad pH spectrum, profile overview Oryza sativa Japonica Group

Cofactor

Cofactor Comment Organism Structure
[2Fe-2S]-center
-
 Oryza sativa Japonica Group
[2Fe-2S]-center OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis Oryza sativa Japonica Group

General Information

General Information Comment 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