1.13.11.71: carotenoid-9',10'-cleaving dioxygenase
This is an abbreviated version!
For detailed information about carotenoid-9',10'-cleaving dioxygenase, go to the full flat file.
Word Map on EC 1.13.11.71
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1.13.11.71
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retinoids
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lutein
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grey
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all-trans-retinal
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zeaxanthin
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15,15'-monooxygenase
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lycopene
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oviparous
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ornamental
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hamilton
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captive
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vitellogenesis
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loach
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queen
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strigolactone
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synthesis
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csf1r
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junglefowl
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agriculture
- 1.13.11.71
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retinoids
- lutein
-
grey
- all-trans-retinal
- zeaxanthin
-
15,15'-monooxygenase
- lycopene
-
oviparous
-
ornamental
- hamilton
-
captive
-
vitellogenesis
- loach
-
queen
- strigolactone
- synthesis
- csf1r
- junglefowl
- agriculture
Reaction
Synonyms
BC-9',10'-oxygenase, Bcdo2, BCO2, beta,beta-carotene 9',10'-dioxygenase 2, beta,beta-carotene 9',10'-oxygenase, beta,beta-carotene-9',10'-dioxygenase, beta,beta-carotene-9',10'-dioxygenase 2, beta,beta-carotene-9,10-oxygenase 2, beta-carotene 9',10' oxygenase, beta-carotene 9',10'-oxygenase, beta-carotene-9',10'-oxygenase, beta-carotene-9,10'-oxygenase, CCD1, CCD4b, CCD7, LjCCD7, ScBCO2, xanthophyll cleavage enzyme
ECTree
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Substrates Products
Substrates Products on EC 1.13.11.71 - carotenoid-9',10'-cleaving dioxygenase
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REACTION DIAGRAM
9-cis-beta-carotene + O2
9-cis-beta-apo-10'-carotenal + beta-ionone
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beta-carotene + O2
beta-cyclocitral + beta-ionone
the enzyme is able to break the 9,10 (9',10') and 7,8 (7',8') double-bonds of beta-carotene
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?
beta-cryptoxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + beta-ionone
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?
beta-cryptoxanthin + O2
3-hydroxy-beta-apo-8'-carotenal + beta-cyclocitral
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?
beta-cryptoxanthin + O2
beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
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?
beta-cryptoxanthin + O2
beta-apo-10'-carotenal + ?
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main clevage product is beta-apo-10'-carotenal only small amounts of 3-OH-beta-apocarotenal are formed
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?
lutein + O2
3-hydroxy-alpha-apo-10'-carotenal + 3-hydroxy-beta-ionone
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?
lutein + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-alpha-ionone
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?
lycopene + O2
6-methyl-5-hepten-2-one + ?
the enzyme also possesses oxidative cleavage activity at the 5,6 (5',6') positions of lycopene
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all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
all-trans-beta-carotene + O2
all-trans-10'-apo-beta-carotenal + beta-ionone
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?
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
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?
alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
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?
alpha-carotene + O2
beta-apo-10'-carotenal + alpha-apo-10'-carotenal
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?
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
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?
zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
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?
zeaxanthin + O2
3-hydroxy-beta-apo-10'-carotenal + 3-hydroxy-beta-ionone
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?
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no substrate: lycopene, lutein, zeaxanthin, violaxanthin, or neoxanthin
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additional information
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like BCO1, EC 1.13.11.63, purified recombinant chicken BCO2 catalyzes the oxidative cleavage of the provitamin A carotenoids beta-carotene, alpha-carotene, and beta-cryptoxanthin. Its catalytic activity with beta-carotene as substrate is at least 10fold lower than that of BCO1. Purified recombinant chicken BCO2 also catalyzes the oxidative cleavage of 9-cis-beta-carotene and the non-provitamin A carotenoids zeaxanthin and lutein, and is inactive with all-trans-lycopene and beta-apo-carotenoids. Apo-10'-carotenoids are detected as enzymatic products by HPLC, and the identities are confirmed by LC-MS. Small amounts of 3-hydroxy-beta-apo-8'-carotenal are also consistently detected in BCO2-beta-cryptoxanthin reaction mixtures. With the exception of this activity with beta-cryptoxanthin, BCO2 cleaves specifically at the 9'-10'-bond to produce apo-10'-carotenoids. BCO2 is regioselective (or even regiospecific) for the trans 9'-10'-end of 9-cis-beta-carotene due to the size of the substrate tunnel. Unlike murine BCO2, chicken BCO2 cannot perform a second cleavage on beta-apo-10'-carotenal to yield rosafluene dialdehyde, and it has no activity with all-trans-lycopene, while it cleaves cis-lycopene isomers. Chicken BCO2 also does not have activity with the other beta-apocarotenals in the series (beta-apo-8'-carotenal, beta-apo-12'-carotenal, and beta-apo-14'-carotenal). Importance of the 3-hydroxy-beta-ionone ring for BCO2 cleavage, preference of BCO2 for substrates that contain a 3-hydroxy-beta-ionone ring
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additional information
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inactivity of BCO2 with xanthophylls such as zeaxanthin
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additional information
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inactivity of BCO2 with xanthophylls such as zeaxanthin
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additional information
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human BCO2 isoform a (human BCO2a) fails to cleave zeaxanthin, retaining the yellow color
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additional information
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human BCO2 isoform a (human BCO2a) fails to cleave zeaxanthin, retaining the yellow color
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additional information
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ScBCO2-catalyzed conversion of beta-carotene to beta-apo-10'-carotenal is followed by HPLC and LC-MS
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additional information
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enzyme ScBCO2 only exhibits cleavage activity towards carotenoid substrates containing two beta-ionone rings and its catalytic efficiency (kcat/Km) follows the descending order beta-carotene, alpha-carotene, lutein
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additional information
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ScBCO2-catalyzed conversion of beta-carotene to beta-apo-10'-carotenal is followed by HPLC and LC-MS
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additional information
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enzyme ScBCO2 only exhibits cleavage activity towards carotenoid substrates containing two beta-ionone rings and its catalytic efficiency (kcat/Km) follows the descending order beta-carotene, alpha-carotene, lutein
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