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Information on EC 2.3.1.211 - bisdemethoxycurcumin synthase and Organism(s) Oryza sativa and UniProt Accession Q8LIL0

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EC Tree
IUBMB Comments
A polyketide synthase characterized from the plant Oryza sativa (rice) that catalyses the formation of the C6-C7-C6 diarylheptanoid scaffold of bisdemethoxycurcumin. Unlike the process in the plant Curcuma longa (turmeric), where the conversion is carried out via a diketide intermediate by two different enzymes (EC 2.3.1.218, phenylpropanoylacetyl-CoA synthase and EC 2.3.1.217, curcumin synthase), the diketide intermediate formed by this enzyme remains within the enzyme's cavity and is not released to the environment.
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Oryza sativa
UNIPROT: Q8LIL0
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Word Map
The taxonomic range for the selected organisms is: Oryza sativa
The enzyme appears in selected viruses and cellular organisms
Synonyms
curcuminoid synthase, clpks10, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
curcuminoid synthase
-
Os07g0271500
-
curcuminoid synthase
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
show the reaction diagram
no head-to-tail synthesis, the reaction begins with the thioesterification of the thiol moiety of Cys-174 by a starter molecule, 4-coumaroyl-CoA. Decarboxylative condensation of the first extender substrate, malonyl-CoA, onto the thioester of 4-coumarate results in the formation of a diketide-CoA intermediate. Subsequent hydrolysis of the intermediate yields a beta-keto acid, which in turn acts as the second extender substrate. The beta-keto acid is then joined to the Cys-174-bound 4-coumarate by decarboxylative condensation to form bisdemethoxycurcumin
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
4-coumaroyl-CoA:malonyl-CoA 4-coumaryltransferase (bisdemethoxycurcumin-forming)
A polyketide synthase characterized from the plant Oryza sativa (rice) that catalyses the formation of the C6-C7-C6 diarylheptanoid scaffold of bisdemethoxycurcumin. Unlike the process in the plant Curcuma longa (turmeric), where the conversion is carried out via a diketide intermediate by two different enzymes (EC 2.3.1.218, phenylpropanoylacetyl-CoA synthase and EC 2.3.1.217, curcumin synthase), the diketide intermediate formed by this enzyme remains within the enzyme's cavity and is not released to the environment.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
show the reaction diagram
-
a minor product is a triketide pyrone formed from one 4-coumaroyl-CoA and two malonyl-CoAs. No formation of 5-(4-hydroxyphenyl)-3-oxo-pent-4-enoic acid and 4-hydroxybenzalacetone
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2H-pyran-2-one + curcumin
show the reaction diagram
very low activity
-
-
?
cinnamoyl-CoA + 2 malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 2 CO2
show the reaction diagram
-
cinnamoyl-CoA reacts to form a triketide pyrone with a small amount of dicinnamoylmethane
-
?
cinnamoyl-CoA + 3-oxo-octanoate + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
show the reaction diagram
-
-
-
?
cinnamoyl-CoA + 3-oxo-octanoyl-N-acetylcysteamine thioester + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
show the reaction diagram
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
show the reaction diagram
2 cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + dicinnamoylmethane + 2 CO2
show the reaction diagram
-
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
show the reaction diagram
4-coumaroyl-CoA + 3-oxodecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)dodeca-1,4-dien-3-one + CoA + CO2 + H2O
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + 3-oxododecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)tetradeca-1,4-dien-3-one + CoA + CO2 + H2O
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + 3-oxooctanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)deca-1,4-dien-3-one + CoA + CO2 + H2O
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + 3-oxotetradecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)hexadeca-1,4-dien-3-one + CoA + CO2 + H2O
show the reaction diagram
-
-
-
-
?
4-coumaroyl-CoA + cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + cinnamoyl-4-coumaroyl-methane + 2 CO2
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
show the reaction diagram
-
-
-
?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
show the reaction diagram
-
-
-
-
?
2 cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + dicinnamoylmethane + 2 CO2
show the reaction diagram
-
-
-
-
?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
show the reaction diagram
-
-
-
-
?
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8
activity range, profile overview
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
26
-
in vivo assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 60
activity range, profile overview
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
curcuminoid synthase is a plant-specific single type III polyketide synthase, i.e. type III PKS, and belongs to the chalcone synthase superfamily of type III polyketide synthases
evolution
-
curcuminoid synthase is a plant-specific type III polyketide synthase and belongs to the chalcone synthase superfamily of type III polyketide synthases
additional information
-
enzyme structure-function relationship, overview
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
43000
x * 43000, recombinant His-tagged enzyme, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 43000, recombinant His-tagged enzyme, SDS-PAGE
additional information
-
enzyme structure-function relationship, overview
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified recombinant His6-tagged enzyme, sitting drop vapour diffusion method, optimization of the crystallization conditions, mixing 0.0005 ml of protein solution, containing 10 mg/ml in 20 mM HEPES-NaOH, pH 7.0, 100 mM NaCl, and 2 mM DTT, with an equal volume of reservoir solution, containing 100 mM HEPES-NaOH, pH 7.8, 1995 mM ammonium sulfate, 3% dimethylsulfoxide, and 2 mM CoA, and equilibration against 0.1 ml reservoir solution, 20°C, cryoprotection in 100 mM HEPES-NaOH pH 7.8, 1330 mM ammonium sulfate, 2 mM CoA, 12% v/v glycerol and 14% w/v PEG 400, X-ray diffraction structure determination and analysis st 2.5 A resolution
-
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3)
recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3)-pLysS by nickel affinity and anion exchange chromatography, followed by gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression of the His-tagged enzyme in Escherichia coli strain BL21 (DE3)
gene AK109558, expression of His6-tagged CUS in Escherichia coli strain BL21(DE3)-pLysS
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
engineering of an in vivo reporter assay for phenylalanine ammonia-lyase efficiency in Escherichia coli based on a plant type III polyketide biosynthetic pathway. The candidate phenylalanine ammonia-lyases are coexpressed with 4-coumarate:CoA ligase 4CL1 from Arabidopsis thaliana and curcuminoid synthase from Oryza sativa. A microplate-based assay is used to measure the titer of dicinnamoylmethane
synthesis
an engineered Escherichia coli strain expressing phenylalanine ammonia-lyase, 4-coumarate:CoA ligase 4CL1 from Arabidopsis thaliana and curcuminoid synthase from Oryza sativa leads to the production of dicinnamoylmethane at a high level of 0.36 g/l. Supplement of 2-fluoro-phenylalanine yields fluorinated dicinnamoylmethane derivatives, 6,6'-difluorodicinnamoylmethane and 6-fluoro-dicinnamoylmethane, of which the latter is a new curcuminoid
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Katsuyama, Y.; Matsuzawa, M.; Funa, N.; Horinouchi, S.
Production of curcuminoids by Escherichia coli carrying an artificial biosynthesis pathway
Microbiology
154
2620-2628
2008
Oryza sativa
Manually annotated by BRENDA team
Morita, H.; Wanibuchi, K.; Nii, H.; Kato, R.; Sugio, S.; Abe, I.
Structural basis for the one-pot formation of the diarylheptanoid scaffold by curcuminoid synthase from Oryza sativa
Proc. Natl. Acad. Sci. USA
107
19778-19783
2010
Oryza sativa
Manually annotated by BRENDA team
Morita, H.; Wanibuchi, K.; Kato, R.; Sugio, S.; Abe, I.
Expression, purification and crystallization of a plant type III polyketide synthase that produces diarylheptanoids
Acta Crystallogr. Sect. F
66
948-950
2010
Oryza sativa
Manually annotated by BRENDA team
Katsuyama, Y.; Ohnishi, Y.; Horinouchi, S.
Production of dehydrogingerdione derivatives in Escherichia coli by exploiting a curcuminoid synthase from Oryza sativa and a beta-oxidation pathway from Saccharomyces cerevisiae
ChemBioChem
11
2034-2041
2010
Oryza sativa
Manually annotated by BRENDA team
Katsuyama, Y.; Matsuzawa, M.; Funa, N.; Horinouchi, S.
In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa
J. Biol. Chem.
282
37702-37709
2007
Oryza sativa (Q8LIL0), Oryza sativa
Manually annotated by BRENDA team
Wang, S.; Zhang, S.; Zhou, T.; Zeng, J.; Zhan, J.
Design and application of an in vivo reporter assay for phenylalanine ammonia-lyase
Appl. Microbiol. Biotechnol.
97
7877-7885
2013
Oryza sativa (Q8LIL0), Oryza sativa
Manually annotated by BRENDA team