BRENDA home
History
Information on EC 5.2.1.14 - beta-carotene isomerase
for references in articles please use BRENDA:EC5.2.1.14Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
5.2.1.14 beta-carotene isomeraseIUBMB Comments
The enzyme participates in a pathway leading to biosynthesis of strigolactones, plant hormones involved in promotion of symbiotic associations known as arbuscular mycorrhiza.
Specify your search results
Word Map
- 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
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
dwarf27, osd27, 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
beta-carotene isomerase
D27
DWARF27
DWARF27
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
all-trans-beta-carotene = 9-cis-beta-carotene
-
-
-
-
all-trans-beta-carotene = 9-cis-beta-carotene
Oryza sativa Japonica Group
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
MetaCyc
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
all-trans-beta,beta-cryptoxanthin
9-cis-beta,beta-cryptoxanthin
-
-
-
r
alpha-carotene
9-cis-alpha-carotene + 9'-cis-alpha-carotene
-
-
-
?
9-cis-beta-carotene
all-trans-beta-carotene
reaction is reversible, the conversion of 9-cis- into all-trans-beta-carotene is the preferred reaction
-
-
r
additional information
?
-
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
-
-
?
additional information
?
-
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
[2Fe-2S]-center
OsD27 contains a [2Fe-2S] iron-sulfur cluster that is required for catalysis
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
enzyme is not inhibited by hydroxamic acids that cause shoot branching in planta, but D27 is partially inhibited by terpene-like hydroxamic acids; 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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
metabolism
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
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
the phenotype of d27 is correlated with enhanced polar auxin transport. The enzyme regulates rice tiller bud outgrowth
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
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Mitochondrion (Reliability: 4)
D27_MEDTR
252
0
28434
Swiss-Prot
other Location (Reliability: 3)
D27_ORYSJ
278
0
30759
Swiss-Prot
Chloroplast (Reliability: 5)
A0A0B2SSL4_GLYSO
270
0
30074
TrEMBL
Chloroplast (Reliability: 4)
A0A445LI17_GLYSO
275
0
30144
TrEMBL
Mitochondrion (Reliability: 4)
A0A445LI76_GLYSO
224
0
24561
TrEMBL
Mitochondrion (Reliability: 4)
A0A445LCG8_GLYSO
253
0
28516
TrEMBL
other Location (Reliability: 5)
A0A445LLQ5_GLYSO
232
0
26449
TrEMBL
other Location (Reliability: 2)
A0A2P6PVN8_ROSCH
263
0
29451
TrEMBL
Mitochondrion (Reliability: 5)
A0A445LCS9_GLYSO
251
0
28458
TrEMBL
other Location (Reliability: 5)
G7J804_MEDTR
266
0
29887
TrEMBL
Mitochondrion (Reliability: 4)
A0A2P6P463_ROSCH
264
0
29840
TrEMBL
Mitochondrion (Reliability: 4)
A0A445IGF4_GLYSO
272
0
29645
TrEMBL
Chloroplast (Reliability: 5)
A0A445H9D6_GLYSO
291
0
32661
TrEMBL
Mitochondrion (Reliability: 3)
G7ICW5_MEDTR
260
0
28294
TrEMBL
Chloroplast (Reliability: 5)
A0A445LLA8_GLYSO
207
0
23466
TrEMBL
other Location (Reliability: 2)
A0A445IGT7_GLYSO
221
0
23835
TrEMBL
Chloroplast (Reliability: 5)
A0A2G9GWL9_9LAMI
269
0
30094
TrEMBL
Secretory Pathway (Reliability: 5)
A0A445LI42_GLYSO
244
0
27207
TrEMBL
other Location (Reliability: 3)
A0A445LNU6_GLYSO
274
0
30704
TrEMBL
other Location (Reliability: 4)
A0A0B2QB74_GLYSO
249
0
27865
TrEMBL
other Location (Reliability: 4)
A0A445LLA7_GLYSO
164
0
18543
TrEMBL
Secretory Pathway (Reliability: 5)
A0A445LNU3_GLYSO
241
0
27050
TrEMBL
other Location (Reliability: 4)
A0A072U3B7_MEDTR
248
0
28285
TrEMBL
Mitochondrion (Reliability: 5)
A0A2P6RFK1_ROSCH
269
0
30191
TrEMBL
Chloroplast (Reliability: 2)
A0A445IH93_GLYSO
256
0
28779
TrEMBL
Mitochondrion (Reliability: 5)
A0A2G9H5Q3_9LAMI
233
0
26168
TrEMBL
Mitochondrion (Reliability: 5)
A0A0B2RIH6_GLYSO
266
0
29688
TrEMBL
Mitochondrion (Reliability: 3)
A0A445LLA6_GLYSO
809
0
90091
TrEMBL
other Location (Reliability: 2)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene DWARF27, recombinant expression in Escherichia coli strain BL21
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is rapidly induced by rhizobium lipo-chitooligosaccharide signals in an NSP1 and NSP2-dependent manner
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Select items on the left to see more content.
EXTERNAL LINKS (specific for EC-Number 5.2.1.14)
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
About BRENDA
Help
Download
Contribution
member of
curated at
curated at
Server: brenda6 Ver: 5bbdedc-main (2022-08-15 08:50:02 +0200)