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2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
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
2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
curcuminoid synthase catalyzes the formation of diketide-CoA by condensing 4-coumaroyl-CoA and malonyl-CoA. The resulting diketide-CoA is hydrolyzed and converted to a beta-keto acid. Finally, curcuminoid synthase catalyzes a decarboxylative condensation of the beta-keto acid with another molecule of 4-coumaroyl-CoA, to synthesize curcuminoid
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2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
the reaction proceeds in three steps via formation of 4-coumaroyldiketide-CoA and 4-coumaroyl beta-keto acid, overview
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2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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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
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?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2H-pyran-2-one + curcumin
very low activity
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?
cinnamoyl-CoA + 2 malonyl-CoA + H2O
3 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 2 CO2
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cinnamoyl-CoA reacts to form a triketide pyrone with a small amount of dicinnamoylmethane
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cinnamoyl-CoA + 3-oxo-octanoate + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
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cinnamoyl-CoA + 3-oxo-octanoyl-N-acetylcysteamine thioester + H2O
CoA + cinnamoyl(hexanoyl)methane + ?
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?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
2 cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + dicinnamoylmethane + 2 CO2
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?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
4-coumaroyl-CoA + 3-oxodecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)dodeca-1,4-dien-3-one + CoA + CO2 + H2O
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?
4-coumaroyl-CoA + 3-oxododecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)tetradeca-1,4-dien-3-one + CoA + CO2 + H2O
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?
4-coumaroyl-CoA + 3-oxooctanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)deca-1,4-dien-3-one + CoA + CO2 + H2O
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?
4-coumaroyl-CoA + 3-oxotetradecanoyl-CoA
(1E,4Z)-5-hydroxy-1-(4-hydroxyphenyl)hexadeca-1,4-dien-3-one + CoA + CO2 + H2O
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4-coumaroyl-CoA + cinnamoyl-CoA + malonyl-CoA + H2O
3 CoA + cinnamoyl-4-coumaroyl-methane + 2 CO2
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additional information
?
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2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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curcuminoid synthase catalyzes the formation of diketide-CoA by condensing 4-coumaroyl-CoA and malonyl-CoA. The resulting diketide-CoA is hydrolyzed and converted to a beta-keto acid. Finally, curcuminoid synthase catalyzes a decarboxylative condensation of the beta-keto acid with another molecule of 4-coumaroyl-CoA, to synthesize curcuminoid
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?
2 4-coumaroyl-CoA + malonyl-CoA + H2O
3 CoA + bisdemethoxycurcumin + 2 CO2
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the reaction proceeds in three steps via formation of 4-coumaroyldiketide-CoA and 4-coumaroyl beta-keto acid, overview
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?
2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
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2 feruloyl-CoA + malonyl-CoA + H2O
3 CoA + curcumin + 2 CO2
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the reaction proceeds in three steps via formation of feruloyldiketide-CoA and feruloyl beta-keto acid, overview
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?
additional information
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enzyme substrate specificity, mass spectrometric product analysis, curcuminoid synthase prefers 4-coumaroyl-CoA 2fold to cinnamoyl-CoA, detailed overview. Curcuminoid synthase appears to be capable of the synthesis of not only diarylheptanoids but also gingerol analogues, because it synthesized cinnamoyl(hexanoyl)methane, a putative intermediate of gingerol, from cinnamoyl-CoA and 3-oxooctanoic acid, feruloyl-CoA is a poor substrate, no activity with 3-oxo-5-phenyl-pent-4-enoic acid and 3-oxooctanoic acid as substrates. Products of curcuminoid synthase from diketide intermediates, relaxed specificity for the second extender substrate, overview
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additional information
?
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enzyme substrate specificity, mass spectrometric product analysis, curcuminoid synthase prefers 4-coumaroyl-CoA 2fold to cinnamoyl-CoA, detailed overview. Curcuminoid synthase appears to be capable of the synthesis of not only diarylheptanoids but also gingerol analogues, because it synthesized cinnamoyl(hexanoyl)methane, a putative intermediate of gingerol, from cinnamoyl-CoA and 3-oxooctanoic acid, feruloyl-CoA is a poor substrate, no activity with 3-oxo-5-phenyl-pent-4-enoic acid and 3-oxooctanoic acid as substrates. Products of curcuminoid synthase from diketide intermediates, relaxed specificity for the second extender substrate, overview
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?
additional information
?
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the enzyme is capable of synthesizing gingerol-related compounds by condensing 4-coumaroyl-CoA with 3-oxooctanoic acid (a beta-keto acid), or with 3-oxoocarboxyl-N-acetylcysteamine thioester, a diketide-CoA analogue, in vitro. The enzyme is inactive with 3-oxoacyl derivatives of chain lengths beow C8 and above C14, overview
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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
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additional information
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construction of an artificial curcuminoid biosynthetic pathway, including reactions of phenylalanine ammonia-lyase from the yeast Rhodotorula rubra, 4-coumarate:CoA ligase from Lithospermum erythrorhizon and curcuminoid synthase from Oryza sativa in Escherichia coli for the production of curcuminoids. Cultivation of the recombinant Escherichia coli cells in the presence of tyrosine or phenylalanine, or both, leads to production of bisdemethoxycurcumin, dicinnamoylmethane and cinnamoyl-4-coumaroylmethane, overview. Another Escherichia coli system carrying the 4-coumarate:CoA ligase and the CUS genes is also useful for high-yield production of curcuminoids from exogenously supplemented phenylpropanoid acids 4-coumaric acid, cinnamic acid and ferulic acid
additional information
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production of several dehydrogingerdione (a gingerol derivative) analogues from a recombinant Escherichia coli strain in which an artificial biosynthesis pathway for dehydrogingerdione is reconstructed that is not based on the original biosynthesis pathway of gingerol derivatives in plants. The system consists of a 4-coumarate:CoA ligase from Lithospermum erythrorhizon, a fatty acid CoA ligase from Oryza sativa, a beta-oxidation system from Saccharomyces cerevisiae, and a curcuminoid synthase from Oryza sativa
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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
brenda
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
brenda
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
brenda
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
brenda
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
brenda
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
brenda