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Information on EC 1.13.11.68 - 9-cis-beta-carotene 9',10'-cleaving dioxygenase and Organism(s) Arabidopsis thaliana and UniProt Accession Q7XJM2
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1.13.11.68 9-cis-beta-carotene 9',10'-cleaving dioxygenaseIUBMB Comments
Requires Fe2+. The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
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Word Map
- 1.13.11.68
- strigolactones
- sls
- shoot
-
phytohormone
-
axillary
- dwarf27
-
tillering
- carlactone
-
weed
-
carotenoid-derived
-
apocarotenoids
- phelipanche
- ramosa
- orobanche
-
arbuscular
The taxonomic range for the selected organisms is: Arabidopsis thaliana
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
atccd7, ccd4b, carotenoid cleavage dioxygenase 7, carotenoid cleavage dioxygenases 7, osccd7, psccd7, max3/ccd7, zmccd7, sl biosynthetic enzyme, zpccd7, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CCD7
MAX3
NCED7
-
-
-
-
CCD7
-
-
-
-
MAX3
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
9-cis-beta-carotene:O2 oxidoreductase (9',10'-cleaving)
Requires Fe2+. The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(7E,7'E,9Z,9'E)-7',8'-dihydro-psi,psi-carotene + O2
zeta-apo-10'-carotenal + beta-ionone
-
-
-
?
(7E,7'E,9Z,9'E)-lycopene + O2
zeta-apo-10'-carotenal + beta-ionone
-
-
-
?
9'-cis-neurosporene + O2
zeta-apo-10'-carotenal + beta-ionone
low activity
-
-
?
9-cis-lutein + O2
9-cis-3-hydroxy-epsilon-apo-10'-carotenal + 3-hydroxy-beta-ionone
-
-
-
?
9-cis-zeaxanthin + O2
9-cis-3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
-
-
-
?
9-cis-zeta-carotene + O2
9-cis-zeta-apo-10'-carotenal + beta-ionone
-
-
-
?
9-cis-beta-carotene + 02
9-cis-beta-apo-10'-carotenal + beta-ionone
-
-
-
-
?
9-cis-beta-carotene + O2
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
-
?
9-cis-lutein + O2
9-cis-3-hydroxy-epsilon-apo-10'-carotenal + ?
-
-
-
-
?
9-cis-zeaxanthin + O2
9-cis-3-hydroxy-beta-apo-10'-carotenal + ?
-
-
-
-
?
9-cis-beta-carotene + O2
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
?
9-cis-beta-carotene + O2
9-cis-10'-apo-beta-carotenal + beta-ionone
AtCCD7 preferentially cleaves 9-cis-beta-carotene
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-
?
additional information
?
-
no substrate: lycopene, lutein, zeaxanthin, violaxanthin, or neoxanthin
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-
?
additional information
?
-
substrate- and stereospecificity of Arabidopsis thaliana carotenoid cleavage dioxygenase 7, overview
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-
?
additional information
?
-
AtCCD7 cleaves asymmetrically at the 9, 10, and 9', 10' bonds
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-
?
additional information
?
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enzyme CCD7 cleaves different 9-cis-carotenoids, yielding hydroxylated 9-cis-apo-10'-carotenals that may lead to hydroxylated carlactones, but show highest affinity for 9-cis-beta-carotene. The enzyme has a higher affinity to 9-cis-beta-carotene than to 9-cis-zeaxanthin, but converts the latter with higher rate. No detectable conversion of 9-cis-violaxanthin, all-trans-lutein, -zeaxanthin or -cryptoxanthin
-
-
?
additional information
?
-
enzyme substrate specificity, dynamic modeling, overview. No activity with the tri-cis-configured PDS or ZDS intermediates and products, i.e. 9,15-di-cis-phytofluene, 9,15,9'-tri-cis-zeta-carotene, 7,9,9'-tri-cis-neurosporene, and 7,9,9',7-tetra-cis-lycopene, as well as with non-canonical isomers of phytofluene (9-cis, 15-cis, all-trans). 9-cis-Lycopene is a poor substrate, and all-trans-lycopene is no substrate. AtCCD7 shows specificity for cleavage of the trans-configured C9-C10 double bond
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-
?
additional information
?
-
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the enzyme does not act on 9-cis-violaxanthin
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-
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
9-cis-beta-carotene + O2
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
?
9-cis-zeaxanthin + O2
9-cis-3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
-
-
-
?
9-cis-beta-carotene + O2
9-cis-10'-apo-beta-carotenal + beta-ionone
-
-
-
-
?
additional information
?
-
substrate- and stereospecificity of Arabidopsis thaliana carotenoid cleavage dioxygenase 7, overview
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
methanol
addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0411
9-cis-beta-carotene
recombinant enzyme, pH not specified in the publication, 28°C
0.1487
9-cis-zeaxanthin
recombinant enzyme, pH not specified in the publication, 28°C
0.0152
beta-carotene
pH 7.0, temperature not specified in the publication
additional information
additional information
Michaelis-Menten kinetics
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
protein contains a probable chloroplast targeting sequence of 31 amino acids
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
occurrence of duplication in CCD4 genes that evolved into two new genes CCD7 and CCD8, EC 1.13.11.70. The site-specific profile and coefficient of type-I functional divergences reveals critical amino acid residues, leading to subgroup-specific functional evolution after their phylogenetic diversification
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
physiological function
additional information
physiological function
coexpression of the enzyme, CCD7, and all-trans-10'-apo-beta-carotenal 13,14-cleaving dioxygenase CCD8, EC 1.13.11.70, in Escherichia coli results in production of 13-apo-beta-carotenone. The sequential cleavages of beta-carotene by CCD7 and CCD8 are likely the initial steps in the synthesis of a carotenoid-derived signaling molecule that is necessary for the regulation lateral branching
physiological function
loss-of-function mutants exhibit a significant decrease in petiole length and are highly branched. The axillary buds, which are typically delayed in growth in wild-type plants, grow out to produce leaves and inflorescences. The mutant plant have smaller rosette diameters due to a decrease in the lengths of petioles and leaf blades compared with wild-type plants. The phenotypes contribute to the bushy appearance of the mutants. The double mutant, additionally lacking 10'-apo-beta-carotenal 13,14-cleaving dioxygenase activity, EC 1.13.11.70, is phenotypically indistinguishable from either single mutant, indicating an interaction consistent with both genes functioning in the same pathway. Both classes of plants show a slight increase in inflorescence number compared with wild type
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
physiological function
CCD7 enzymes are highly stereospecific, cleaving only 9-cis-configured substrates, such as 9-cis-beta-carotene. The strigolactone biosynthetic enzyme AtCCD7 converts 9-cis-configured acyclic carotenes, such as 9-cis-zeta-carotene, 9'-cis-neurosporene, and 9-cis-lycopene, yielding 9-cis-configured products and indicating that AtCCD7, rather than AtCCD4, is the candidate for forming acyclic retrograde signals that are thought to derive from the cleavage of poly-cis-configured carotene desaturation intermediates
physiological function
strigolactones are phytohormones synthesized from carotenoids via a stereospecific pathway involving the carotenoid cleavage dioxygenases 7 (CCD7) and 8. CCD7 cleaves 9-cis-beta-carotene to form a supposedly 9-cis-configured beta-apo-10'-carotenal
additional information
in silico analysis, structure homology modeling, molecular modeling, dynamic simulation and structure comparisons of Arabidopsis thaliana carotenoid cleavage dioxygenases, overview
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
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). CCD7_ARATH
618
0
69453
Swiss-Prot
Chloroplast (Reliability: 3)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
a truncated enzyme protein of 587 amino acids lacking the N-terminal targeting sequence is also able to catalyze the 910 cleavage of beta-carotene. Coexpression of the enzyme, CCD7, and all-trans-10'-apo-beta-carotenal 13,14-cleaving dioxygenase CCD8, EC 1.13.11.70, in Escherichia coli results in production of 13-apo-beta-carotenone. The sequential cleavages of beta-carotene by CCD7 and CCD8 are likely the initial steps in the synthesis of a carotenoid-derived signaling molecule that is necessary for the regulation lateral branching
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Methanol
addition of methanol to in vitro assays has a stimulatory effect on activity at concentrations up to 25%
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant GST-tagged AtCCD7 from Escherichia coli by glutathione affinity chromatographyy
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene ccd7, recombinant expression in Escherichia coli strain BL21(DE3)
gene ccd7, recombinant expression of GST-tagged AtCCD7 in Escherichia coli
expressed as a thioredoxin and GST fusion proteins in Escherichia coli
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Schwartz, S.H.; Qin, X.; Loewen, M.C.
The biochemical characterization of two carotenoid cleavage enzymes from Arabidopsis indicates that a carotenoid-derived compound inhibits lateral branching
J. Biol. Chem.
279
46940-46945
2004
Arabidopsis thaliana (Q7XJM2)
Auldridge, M.E.; Block, A.; Vogel, J.T.; Dabney-Smith, C.; Mila, I.; Bouzayen, M.; Magallanes-Lundback, M.; DellaPenna, D.; McCarty, D.R.; Klee, H.J.
Characterization of three members of the Arabidopsis carotenoid cleavage dioxygenase family demonstrates the divergent roles of this multifunctional enzyme family
Plant J.
45
982-993
2006
Arabidopsis thaliana (Q7XJM2)
Alder, A.; Jamil, M.; Marzorati, M.; Bruno, M.; Vermathen, M.; Bigler, P.; Ghisla, S.; Bouwmeester, H.; Beyer, P.; Al-Babili, S.
The path from beta-carotene to carlactone, a strigolactone-like plant hormone
Science
335
1348-1351
2012
Arabidopsis thaliana, Oryza sativa, Pisum sativum
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
FEBS J.
282
3986-4000
2015
Arabidopsis thaliana (Q7XJM2), Arabidopsis thaliana
Bruno, M.; Hofmann, M.; Vermathen, M.; Alder, A.; Beyer, P.; Al-Babili, S.
On the substrate- and stereospecificity of the plant carotenoid cleavage dioxygenase 7
FEBS Lett.
588
1802-1807
2014
Pisum sativum, Arabidopsis thaliana (Q7XJM2)
Priya, R.; Sneha, P.; Rivera Madrid, R.; Doss, C.G.P.; Singh, P.; Siva, R.
Molecular modeling and dynamic simulation of Arabidopsis thaliana carotenoid cleavage dioxygenase gene a comparison with Bixa orellana and Crocus sativus
J. Cell. Biochem.
118
2712-2721
2017
Arabidopsis thaliana (Q7XJM2)
Bruno, M.; Koschmieder, J.; Wuest, F.; Schaub, P.; Fehling-Kaschek, M.; Timmer, J.; Beyer, P.; Al-Babili, S.
Enzymatic study on AtCCD4 and AtCCD7 and their potential to form acyclic regulatory metabolites
J. Exp. Bot.
67
5993-6005
2016
Arabidopsis thaliana (Q7XJM2)
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