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Information on EC 5.2.1.14 - beta-carotene isomerase
for references in articles please use BRENDA:EC5.2.1.14
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EC Tree 5 Isomerases
5.2 cis-trans-Isomerases
5.2.1 cis-trans Isomerases (only sub-subclass identified to date)
5.2.1.14 beta-carotene isomerase
IUBMB Comments
The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
The enzyme appears in viruses and cellular organisms
- 5.2.1.14
- strigolactones
- sls
-
carotenoid
- dioxygenases
- shoot
-
axillary
-
outgrowth
- carlactone
-
symbiotic
- sativa
-
tiller
- lactones
-
terpenoid
-
arbuscular
-
abscisic
-
carotenoid-derived
- truncatula
-
mycorrhizal
-
enol
-
medicago
- nsp1
-
dwarf14
-
agronomic
-
hyphal
-
iron-containing
-
butenolide
-
primordia
-
panicle
-
growth1
-
sl-dependent
-
orobanchol
-
weed
-
d-ring
-
carotenogenesis
showSynonyms
dwarf27, osd27, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
beta-carotene isomerase
D27
DWARF27
DWARF27
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
all-trans-beta-carotene = 9-cis-beta-carotene
-
-
-
-
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
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PATHWAY SOURCE
PATHWAYS
MetaCyc
5-deoxystrigol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
beta-carotene 9-cis-all-trans isomerase
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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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
all-trans-alpha-carotene
9'-cis-alpha-carotene
-
Substrates: -
Products: -
Products: -
?
all-trans-beta-carotene
cis-zeta-carotene
Substrates: -
Products: -
Products: -
r
all-trans-neurosporene
cis-neurosporene
Substrates: -
Products: -
Products: -
r
alpha-carotene
9-cis-alpha-carotene + 9'-cis-alpha-carotene
Substrates: -
Products: -
Products: -
?
9-cis-beta-carotene
all-trans-beta-carotene
Substrates: -
Products: -
Products: -
r
9-cis-beta-carotene
all-trans-beta-carotene
Substrates: reaction is reversible, the conversion of 9-cis- into all-trans-beta-carotene is the preferred reaction
Products: -
Products: -
r
all-trans-beta,beta-cryptoxanthin
9-cis-beta,beta-cryptoxanthin
-
Substrates: low activity
Products: -
Products: -
?
all-trans-beta,beta-cryptoxanthin
9-cis-beta,beta-cryptoxanthin
Substrates: -
Products: -
Products: -
r
all-trans-beta-carotene
9-cis-beta-carotene
-
Substrates: -
Products: -
Products: -
r
all-trans-beta-carotene
9-cis-beta-carotene
Substrates: -
Products: -
Products: -
?, r
all-trans-beta-carotene
9-cis-beta-carotene
Substrates: -
Products: -
Products: -
r
additional information
?
-
-
Substrates: the enzyme does not isomerize 13-cis-beta-carotene, 15-cis-beta-carotene, all-trans-violaxanthin, all-trans-neoxanthin, all-trans-lutein, 9-cis-beta-apo-10'-carotenal, 9-cis-3-hydroxy-beta-apo-10'-carotenal, 9-cis-alpha-apo-10'-carotenal, and 9-cis-3-hydroxy-alpha-apo-10'-carotenal
Products: -
Products: -
?
additional information
?
-
Substrates: substrate specificity of D27 isozymes, overview
Products: -
Products: -
-
additional information
?
-
Substrates: substrate specificity of D27 isozymes, overview
Products: -
Products: -
-
additional information
?
-
Substrates: substrate specificity of D27 isozymes, overview
Products: -
Products: -
-
additional information
?
-
Substrates: 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
Products: -
Products: -
?
additional information
?
-
Substrates: the enzyme is strictly double bond-specific, solely targeting the C9-C10 double bond. DWARF27 does not introduce a 9-cis-double bond in 13-cis- or 15-cis-beta-carotene. Substrates are bicyclic carotenoids, including beta-, alpha-carotene and beta,beta-cryptoxanthin, that contain at least one unsubstituted beta-ionone ring
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
all-trans-beta-carotene
cis-zeta-carotene
Substrates: -
Products: -
Products: -
r
all-trans-neurosporene
cis-neurosporene
Substrates: -
Products: -
Products: -
r
all-trans-beta-carotene
9-cis-beta-carotene
-
Substrates: -
Products: -
Products: -
r
all-trans-beta-carotene
9-cis-beta-carotene
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
[2Fe-2S]-center
OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Iron
Fe2+
OsD27 contains a [2Fe2S] iron-sulfur cluster that is required for catalysis
Iron
presence of an iron-sulfur cluster involved in catalysis
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2E)-N-benzyl-N-hydroxy-3,7-dimethylocta-2,6-dienamide
38% inhibition at 0.1 mM
(2E,4E)-N-benzyl-N-hydroxy-5,9-dimethyldeca-2,4,8-trienamide
33% inhibition at 0.1 mM
3-(3,4-dimethoxyphenyl)-N-hydroxypropanamide
40% inhibition at 0.1 mM
3-amino-N-benzyl-N-hydroxybenzamide
7% inhibition at 0.1 mM
N-benzyl-3-chloro-N-hydroxybenzamide
21% inhibition at 0.1 mM
N-benzyl-N-hydroxy-3,4-dimethoxybenzamide
9% inhibition at 0.1 mM
N-benzyl-N-hydroxy-4-methoxybenzamide
10% inhibition at 0.1 mM
N-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-N-hydroxy-2-(4-methoxyphenyl)acetamide
41% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-3,4-dimethoxybenzamide
25% inhibition at 0.1 mM
N-[(4-fluorophenyl)methyl]-N-hydroxy-4-methoxybenzamide
16% inhibition at 0.1 mM
N1-[(4-fluorophenyl)methyl]-N1-hydroxy-N4-[(4-methoxyphenyl)methyl]butanediamide
40% inhibition at 0.1 mM
sodium 3-[hydroxy[(4-methoxyphenyl)acetyl]amino]propanoate
26% inhibition at 0.1 mM
sodium 3-[hydroxy[(naphthalen-2-yl)acetyl]amino]propanoate
33% inhibition at 0.1 mM
additional information
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; enzyme is not inhibited by hydroxamic acids that cause shoot branching in planta, but D27 is partially inhibited by terpene-like hydroxamic acids
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
D27 is coexpressed with carotenoid cleavage dioxygenases CCD7 and CCD8 in nodule primordia and in the infection zone of mature nodules
brenda
additional information
additional information
identification of one D27 (CsD27-1) and two D27-like (CsD27-2 and CsD27-3) genes in saffron, with CsD27-1 and CsD27-3, clearly differing in their expression patterns. Specifically, CsD27-1 is mainly expressed in the undeveloped stigma and roots, where it is induced by Rhizobium colonization. On the contrary, CsD27-2 and CsD27-3 are mainly expressed in leaves, with a preferential expression of CsD27-3 in this tissue. Isozyme expression pattern, overview
brenda
additional information
identification of one D27 (CsD27-1) and two D27-like (CsD27-2 and CsD27-3) genes in saffron, with CsD27-1 and CsD27-3, clearly differing in their expression patterns. Specifically, CsD27-1 is mainly expressed in the undeveloped stigma and roots, where it is induced by Rhizobium colonization. On the contrary, CsD27-2 and CsD27-3 are mainly expressed in leaves, with a preferential expression of CsD27-3 in this tissue. Isozyme expression pattern, overview
brenda
additional information
identification of one D27 (CsD27-1) and two D27-like (CsD27-2 and CsD27-3) genes in saffron, with CsD27-1 and CsD27-3, clearly differing in their expression patterns. Specifically, CsD27-1 is mainly expressed in the undeveloped stigma and roots, where it is induced by Rhizobium colonization. On the contrary, CsD27-2 and CsD27-3 are mainly expressed in leaves, with a preferential expression of CsD27-3 in this tissue. Isozyme expression pattern, overview
brenda
additional information
identification of one D27 (CsD27-1) and two D27-like (CsD27-2 and CsD27-3) genes in saffron, with CsD27-1 and CsD27-3, clearly differing in their expression patterns. Specifically, CsD27-1 is mainly expressed in the undeveloped stigma and roots, where it is induced by Rhizobium colonization. On the contrary, CsD27-2 and CsD27-3 are mainly expressed in leaves, with a preferential expression of CsD27-3 in this tissue. Isozyme expression pattern, overview. For CsD27-3, its expression level is analyzed in leaves at different time points throughout the day. Fluctuations of the expression level, the isozyme is highly expressed between 10:00 till 14:00, and its expression drops between 22:00 and 02:00
brenda
additional information
identification of one D27 (CsD27-1) and two D27-like (CsD27-2 and CsD27-3) genes in saffron, with CsD27-1 and CsD27-3, clearly differing in their expression patterns. Specifically, CsD27-1 is mainly expressed in the undeveloped stigma and roots, where it is induced by Rhizobium colonization. On the contrary, CsD27-2 and CsD27-3 are mainly expressed in leaves, with a preferential expression of CsD27-3 in this tissue. Isozyme expression pattern, overview. For CsD27-3, its expression level is analyzed in leaves at different time points throughout the day. Fluctuations of the expression level, the isozyme is highly expressed between 10:00 till 14:00, and its expression drops between 22:00 and 02:00
brenda
additional information
identification of one D27 (CsD27-1) and two D27-like (CsD27-2 and CsD27-3) genes in saffron, with CsD27-1 and CsD27-3, clearly differing in their expression patterns. Specifically, CsD27-1 is mainly expressed in the undeveloped stigma and roots, where it is induced by Rhizobium colonization. On the contrary, CsD27-2 and CsD27-3 are mainly expressed in leaves, with a preferential expression of CsD27-3 in this tissue. Isozyme expression pattern, overview. For CsD27-3, its expression level is analyzed in leaves at different time points throughout the day. Fluctuations of the expression level, the isozyme is highly expressed between 10:00 till 14:00, and its expression drops between 22:00 and 02:00
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
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
metabolism
-
D27 is the enzyme providing the substrate for carotenoid cleavage dioxygenase 7 in the course of strigolactone biosynthesis
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
metabolism
chromoplasts and chloroplasts contain carotenoid pigments as all-trans- and cis-isomers, which function as accessory light-harvesting pigments, antioxidant and photoprotective agents, and precursors of signaling molecules and plant hormones. The carotenoid pathway involves the participation of different carotenoid isomerases. Strigolactones (SLs) take part, synergistically with auxins, in the inhibition of corm axillary bud sprouting, and phytoene synthase 3 (CsPSY3) expression is associated with mycorrhizal colonization and strigolactone synthesis
metabolism
chromoplasts and chloroplasts contain carotenoid pigments as all-trans- and cis-isomers, which function as accessory light-harvesting pigments, antioxidant and photoprotective agents, and precursors of signaling molecules and plant hormones. The carotenoid pathway involves the participation of different carotenoid isomerases
physiological function
the phenotype of d27 is correlated with enhanced polar auxin transport. The enzyme regulates rice tiller bud outgrowth
physiological function
-
the enzyme is required for the regulation of axillary branching and the inhibition of secondary bud outgrowth. The enzyme is involved in strigolactone-mediated repression of shoot branching
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
physiological function
D27 is involved in strigolactone biosynthesis in roots upon phosphate stress. The gene is also highly expressed in nodule primordia and subsequently becomes restricted to the meristem and distal infection zone of a mature nodules
physiological function
D27 is a beta-carotene isomerase showing high specificity for the C9-C10 double bond catalyzing the interconversion of all-trans- into 9-cis-beta-carotene, the precursor of strigolactones. Isozymes CsD27-1 catalyzes the isomerization of all-trans- to 9-cis-beta-carotene, and might be involved in the isomerization of zeaxanthin, while CsD27-3 catalyzes the isomerization of all-trans- to cis-zeta-carotene and all-trans- to cis-neurosporene. Isozyme CsD27-1 and CsD27-3 enzymes are both involved in carotenoid isomerization, with CsD27-1 being specific to chromoplast/amyloplast-containing tissue, and CsD27-3 more specific to chloroplast-containing tissues. CsD27-1 is co-expressed with CCD7 and CCD8 mycorrhized roots, whereas CsD27-3 is expressed at higher levels than CRTISO and Z-ISO and showed circadian regulation in leaves. Carotenoids are a class of C40 hydrocarbon compounds formed through the condensation of isoprenoids. They play important roles in numerous physiological processes in plants. In more detail, carotenoids act as accessory pigments in photosynthesis and serve as photoprotective agents by quenching singlet oxygen, which might damage chlorophyll. In addition, carotenoids act as precursors in the biosynthesis of apocarotenoids, such as vitamin A and abscisic acid (ABA) or strigolactones (SLs). In particular, SLs are carotenoid-derived terpenoid lactones that are identified as germination stimulants for parasitic plant seeds
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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). D27_ARATH
264
0
29795
Swiss-Prot
other Location (Reliability: 4)
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene D27-1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, expression analysis
gene D27-2, DNA and amino acid sequence determination and analysis, sequence comparisons, and phylogenetic analysis, expression analysis
gene D27-3, DNA and amino acid sequence determination and analysis, sequence comparisons, and phylogenetic analysis, expression analysis
gene DWARF27, recombinant expression in Escherichia coli strain BL21
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is rapidly induced by rhizobium lipo-chitooligosaccharide signals in an NSP1 and NSP2-dependent manner
in lateral roots, enzyme expression is induced by treatment with auxin and abscisic acid and upon phosphate starvation
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lin, H.; Wang, R.; Qian, Q.; Yan, M.; Meng, X.; Fu, Z.; Yan, C.; Jiang, B.; Su, Z.; Li, J.; Wang, Y.
DWARF27, an iron-containing protein required for the biosynthesis of strigolactones, regulates rice tiller bud outgrowth
Plant Cell
21
1512-1525
2009
Oryza sativa (C7AU21), Oryza sativa
brenda
Waters, M.T.; Brewer, P.B.; Bussell, J.D.; Smith, S.M.; Beveridge, C.A.
The Arabidopsis ortholog of rice DWARF27 acts upstream of MAX1 in the control of plant development by strigolactones
Plant Physiol.
159
1073-1085
2012
Arabidopsis thaliana
brenda
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
Oryza sativa
brenda
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
Oryza sativa Japonica Group (C7AU21)
brenda
van Zeijl, A.; Liu, W.; Xiao, T.; Kohlen, W.; Yang, W.; Bisseling, T.; Geurts, R.
The strigolactone biosynthesis gene DWARF27 is co-opted in rhizobium symbiosis
BMC Plant Biol.
15
260
2015
Medicago truncatula (R4HZ96), Medicago truncatula
brenda
Bruno, M.; Al-Babili, S.
On the substrate specificity of the rice strigolactone biosynthesis enzyme DWARF27
Planta
243
1429-1440
2016
Oryza sativa Japonica Group (C7AU21)
brenda
Abuauf, H.; Haider, I.; Jia, K.P.; Ablazov, A.; Mi, J.; Blilou, I.; Al-Babili, S.
The Arabidopsis DWARF27 gene encodes an all-trans-/9-cis-beta-carotene isomerase and is induced by auxin, abscisic acid and phosphate deficiency
Plant Sci.
277
33-42
2018
Arabidopsis thaliana
brenda
Lopez-Jimenez, A.J.; Morote, L.; Niza, E.; Mondejar, M.; Rubio-Moraga, A.; Diretto, G.; Ahrazem, O.; Gomez-Gomez, L.
Subfunctionalization of D27 isomerase genes in saffron
Int. J. Mol. Sci.
23
10543
2022
Crocus sativus (A0A977SNX7), Crocus sativus (A0A977SNV9), Crocus sativus (A0A977SP62)
brenda
EXTERNAL LINKS (specific for EC-Number 5.2.1.14)
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