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Literature summary for 1.13.11.69 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 1.13.11.69

Cloned(Commentary)

Cloned (Comment) 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 Comment 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 Comment Organism Structure
additional information
-
 additional information two-step kinetic mechanism, pre-steady-state kinetic analysis Arabidopsis thaliana

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
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 Comment Textmining
Arabidopsis thaliana Q8VY26
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His6-tagged AtCCD8 lacking the first 168 bp from Escherichia coli strain BL21 by nickel affinity chromatography Arabidopsis thaliana

Reaction

Reaction Comment 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
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
9-cis-10'-apo-beta-carotenal + 2 O2
-
 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 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 Arabidopsis thaliana ?
-
 ?

Synonyms

Synonyms Comment Organism
carotenoid cleavage dioxygenase
-
 Arabidopsis thaliana
CCD8
-
 Arabidopsis thaliana

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
 assay at Arabidopsis thaliana

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6
-
-
 Arabidopsis thaliana

pH Range

pH Minimum pH Maximum Comment Organism
5.5 9 activity range, profile overview Arabidopsis thaliana

General Information

General Information Comment 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