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Information on EC 1.14.11.B16 - carotenoid 4,4'-beta-ionone ring oxygenase
for references in articles please use BRENDA:EC1.14.11.B16preliminary BRENDA-supplied EC number
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EC Tree
1.14.11.B16 carotenoid 4,4'-beta-ionone ring oxygenaseSpecify your search results
Word Map
- 1.14.11.B16
- astaxanthin
- hydroxylase
-
ketocarotenoids
- haematococcus
- zeaxanthin
- pluvialis
- phytoene
- echinenone
-
desaturase
- lycopene
-
carotenogenic
- adonixanthin
-
xanthophyl
- beta-cryptoxanthin
- zeta-carotene
-
microalgae
- nostoc
- aurantiacum
- alpha-carotene
-
ketolated
- erythropolis
- zofingiensis
- gamma-carotene
- uredovora
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
+
+
+
=
+
+
+
4
Synonyms
beta-carotene ketolase, carotene ketolase, carotenoid 4,4'-beta-ionone ring oxygenase, beta-c-4-oxygenase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4,(4')-beta-ionone ring oxygenase
4,4'beta-oxygenase
beta-C-4-oxygenase
beta-carotene ketolase
bkt
CrtW
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
beta-carotene + 2-oxoglutarate + O2 + H2O = canthaxanthin + succinate + CO2 + 4 H+
echinenone is an intermediary product
-
beta-carotene + 2-oxoglutarate + O2 + H2O = canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
beta-carotene:oxygen 4,4'-oxidoreductase (canthaxanthin-forming)
-
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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
(3R,2'S)-myxol 2'-alpha-L-fucoside + acceptor + O2
(3R,2'S)-4-oxomyxol 2'-alpha-L-fucoside + reduced acceptor
(3R,2'S)-myxol 2'-alpha-L-fucoside + acceptor + O2
(3R,2'S)-4-oxomyxol 2'-alpha-L-fucoside + reduced acceptor
-
-
-
-
?
(3R,2'S)-myxol 2'-alpha-L-fucoside + acceptor + O2
(3R,2'S)-4-oxomyxol 2'-alpha-L-fucoside + reduced acceptor
-
-
-
-
?
3-hydroxyechinenone + acceptor + O2
phoenicoxanthin + reduced acceptor
-
-
-
?
3-hydroxyechinenone + acceptor + O2
phoenicoxanthin + reduced acceptor
-
-
-
?
4-oxozeaxanthin + acceptor + O2
astaxanthin + reduced acceptor
-
-
-
?
4-oxozeaxanthin + acceptor + O2
astaxanthin + reduced acceptor
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
Sphingomonas sp. DC18
-
-
-
-
?
beta-carotene + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
?
beta-carotene + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
?
beta-carotene + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
?
beta-carotene + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
?
beta-carotene + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
-
?
beta-carotene + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
-
?
beta-carotene + acceptor + O2
echinenone + reduced acceptor
-
-
-
?
beta-carotene + acceptor + O2
echinenone + reduced acceptor
-
-
produced in low amounts
-
?
beta-carotene + acceptor + O2
echinenone + reduced acceptor
-
-
produced in low amounts
-
?
echinenone + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
?
echinenone + acceptor + O2
canthaxanthin + reduced acceptor
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
Sphingomonas sp. DC18
-
-
-
-
?
zeaxanthin + acceptor + O2
adonixanthin + reduced acceptor
-
-
-
?
zeaxanthin + acceptor + O2
adonixanthin + reduced acceptor
-
-
-
?
zeaxanthin + acceptor + O2
adonixanthin + reduced acceptor
-
-
-
?
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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
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
beta-carotene + 2-oxoglutarate + O2 + H2O
canthaxanthin + succinate + CO2 + 4 H+
Sphingomonas sp. DC18
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
-
-
-
-
?
zeaxanthin + 2-oxoglutarate + O2 + H2O
astaxanthin + succinate + CO2 + 4 H+
Sphingomonas sp. DC18
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no activation by NAD*, NADP+, NADPH, FAD, FMN
-
additional information
-
no activation by NAD+, NADP+, NADPH, FAD, FMN
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Cysts
Differential expression of carotenogenic genes and associated changes in pigment profile during regeneration of Haematococcus pluvialis cysts.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0143
3-hydroxyechinenone
30°C, 0.4 M Tris/HCl, pH 8.0, 1 mM dithiothreitol, 0.5 mM FeSO4, 5 mM ascorbic acid, 0.5 mM 2-oxoglutarate, 0.1% (mass/vol) deoxycholate
0.0083
4-oxozeaxanthin
30°C, 0.4 M Tris/HCl, pH 8.0, 1 mM dithiothreitol, 0.5 mM FeSO4, 5 mM ascorbic acid, 0.5 mM 2-oxoglutarate, 0.1% (mass/vol) deoxycholate
0.0013
beta-carotene
30°C, 0.4 M Tris/HCl, pH 8.0, 1 mM dithiothreitol, 0.5 mM FeSO4, 5 mM ascorbic acid, 0.5 mM 2-oxoglutarate, 0.1% (mass/vol) deoxycholate
0.002
echinenone
30°C, 0.4 M Tris/HCl, pH 8.0, 1 mM dithiothreitol, 0.5 mM FeSO4, 5 mM ascorbic acid, 0.5 mM 2-oxoglutarate, 0.1% (mass/vol) deoxycholate
0.01
zeaxanthin
30°C, 0.4 M Tris/HCl, pH 8.0, 1 mM dithiothreitol, 0.5 mM FeSO4, 5 mM ascorbic acid, 0.5 mM 2-oxoglutarate, 0.1% (mass/vol) deoxycholate
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.000000083
0.00000015
0.00000017
-
substrate zeaxanthin, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.0000002
-
substrate zeaxanthin, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.000000083
-
substrate beta-carotene, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.000000083
-
substrate zeaxanthin, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.000000083
-
substrate zeaxanthin. 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.000000083
-
substrate beta-carotene, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.00000015
-
substrate beta-carotene, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
0.00000015
-
substrate beta-carotene, 30°C, 0.4 M Tris-HCl, pH 8.0, 1 mM dithiothreitol, 0.1% v/v Tween 60, 3 mM ATP, 0.5 mM FeSO4, 0.5 mM 2-oxoglutarate, 5 mM ascorbic acid
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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). CRTW_PARSN
Paracoccus sp. (strain N81106 / MBIC 01143)
242
5
27128
Swiss-Prot
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Fraser, P.D.; Shimada, H.; Misawa, N.
Enzymic confirmation of reactions involved in routes to astaxanthin formation, elucidated using a direct substrate in vitro assay
Eur. J. Biochem.
252
229-236
1998
Agrobacterium aurantiacum (P54972), Agrobacterium aurantiacum N81106 (P54972)
brenda
Fraser, P.D.; Miura, Y.; Misawa, N.
In vitro characterization of astaxanthin biosynthetic enzymes
J. Biol. Chem.
272
6128-6135
1997
Alcaligenes sp., Haematococcus lacustris, Agrobacterium aurantiacum
brenda
Ye, R.W. Stead, K.J.; Yao, H.; He, H.
Mutational and functional analysis of the beta-carotene ketolase involved in the production of canthaxanthin and astaxanthin
Appl. Environ. Microbiol.
72
5829-5837
2006
Paracoccus sp. (P54972), Paracoccus sp.
brenda
Choi, S.K.; Harada, H.; Matsuda, S.; Misawa, N.
Characterization of two beta-carotene ketolases, CrtO and CrtW, by complementation analysis in Escherichia coli
Appl. Environ. Microbiol.
75
1335-1341
2007
Brevundimonas sp. (Q4W8B8), Brevundimonas sp. SD212 (Q4W8B8)
brenda
Zhu, C.; Naqvi, S.; Capell, T.; Christou, P.
Metabolic engineering of ketocarotenoid biosynthesis in higher plants
Arch. Biochem. Biophys.
483
182-190
2009
Sphingomonas melonis (A3QQZ2), Paracoccus sp. (P54972), Brevundimonas vesicularis (Q0H2C9), Paracoccus haeundaensis (Q24K64), Brevundimonas sp. (Q4W8B8), Paracoccus marcusii (Q9RLH7), Brevundimonas sp. SD212 (Q4W8B8)
brenda
Lotan, T.; Hirschberg, J.
Cloning and expression in Escherichia coli of the gene encoding beta-C-4-oxygenase, that converts beta-carotene to the ketocarotenoid canthaxanthin in Haematococcus pluvialis
FEBS Lett.
364
125-128
1995
Haematococcus lacustris, Haematococcus lacustris 34/7
brenda
Mochimaru, M.; Masukawa, H.; Takaichi, S.
The cyanobacterium Anabaena sp. PCC 7120 has two distinct beta-carotene ketolases: CrtO for echinenone and CrtW for ketomyxol synthesis
FEBS Lett.
579
6111-6114
2005
Anabaena sp., Anabaena sp. PCC 7120
brenda
Breitenbach, J.; Misawa, N.; Kajiwara, S.; Sandmann, G.
Expression in Escherichia coli and properties of the carotene ketolase from Haematococcus pluvialis
FEMS Microbiol. Lett.
140
241-246
1996
Haematococcus lacustris
brenda
Tao, L.; Rouviere, P.E.; Cheng, Q.
A carotenoid synthesis gene cluster from a non-marine Brevundimonas that synthesizes hydroxylated astaxanthin
Gene
379
101-108
2006
Brevundimonas vesicularis (Q0H2C9), Brevundimonas vesicularis DC263 (Q0H2C9)
brenda
Misawa, N.; Satomi, Y.; Kondo, K.; Yokoyama, A.; Kajiwara, S.; Saito, T.; Ohtani, T.; Miki, W.
Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level
J. Bacteriol.
177
6575-6584
1995
Agrobacterium aurantiacum (P54972), Agrobacterium aurantiacum N81106 (P54972)
brenda
Hannibal, L.; Lorquin, J.; D'Ortoli, N.A.; Garcia, N.; Chaintreuil, C.; Masson-Boivin, C.; Dreyfus, B.; Giraud, E.
Isolation and characterization of canthaxanthin biosynthesis genes from the photosynthetic bacterium Bradyrhizobium sp. strain ORS278
J. Bacteriol.
182
3850-3853
2000
Bradyrhizobium sp., Bradyrhizobium sp. ORS278
brenda
Kim, S.H.; Kim, J.H.; Lee, B.Y.; Lee, P.C.
The astaxanthin dideoxyglycoside biosynthesis pathway in Sphingomonas sp. PB304
Appl. Microbiol. Biotechnol.
98
9993-10003
2014
Sphingomonas lacus
brenda
Zhou, P.; Xie, W.; Li, A.; Wang, F.; Yao, Z.; Bian, Q.; Zhu, Y.; Yu, H.; Ye, L.
Alleviation of metabolic bottleneck by combinatorial engineering enhanced astaxanthin synthesis in Saccharomyces cerevisiae
Enzyme Microb. Technol.
100
28-36
2017
Sphingomonas sp. DC18
brenda
Wang, R.; Gu, X.; Yao, M.; Pan, C.; Liu, H.; Xiao, W.; Wang, Y.; Yuan, Y.
Engineering of beta-carotene hydroxylase and ketolase for astaxanthin overproduction in Saccharomyces cerevisiae
Front. Chem. Sci. Engin.
11
89-99
2017
Brevundimonas vesicularis, Brevundimonas vesicularis DC263
-
brenda
Lu, Q.; Bu, Y.F.; Liu, J.Z.
Metabolic engineering of Escherichia coli for producing astaxanthin as the predominant carotenoid
Mar. Drugs
15
E296
2017
Bacillus subtilis, Nostoc punctiforme, Nostoc sp. PCC 7120 = FACHB-418, Sphingomonas sp. DC18, Brevundimonas sp. NBRC 101024, Paracoccus sp. N81106
brenda
Anila, N.; Simon, D.P.; Chandrashekar, A.; Ravishankar, G.A.; Sarada, R.
Metabolic engineering of Dunaliella salina for production of ketocarotenoids
Photosynth. Res.
127
321-333
2016
Dunaliella salina, Dunaliella salina V-101
brenda
Mortimer, C.L.; Misawa, N.; Perez-Fons, L.; Robertson, F.P.; Harada, H.; Bramley, P.M.; Fraser, P.D.
The formation and sequestration of nonendogenous ketocarotenoids in transgenic Nicotiana glauca
Plant Physiol.
173
1617-1635
2017
Brevundimonas sp. NBRC 101024
brenda
Pierce, E.C.; LaFayette, P.R.; Ortega, M.A.; Joyce, B.L.; Kopsell, D.A.; Parrott, W.A.
Ketocarotenoid production in soybean seeds through metabolic engineering
PLoS ONE
10
e0138196
2015
Brevundimonas sp. NBRC 101024 (Q4W8B8)
brenda
Bai, C.; Berman, J.; Farre, G.; Capell, T.; Sandmann, G.; Christou, P.; Zhu, C.
Reconstruction of the astaxanthin biosynthesis pathway in rice endosperm reveals a metabolic bottleneck at the level of endogenous beta-carotene hydroxylase activity
Transgenic Res.
26
13-23
2017
Chlamydomonas reinhardtii
brenda
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