2.3.1.217: curcumin synthase
This is an abbreviated version!
For detailed information about curcumin synthase, go to the full flat file.
Word Map on EC 2.3.1.217
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2.3.1.217
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curcuma
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diketide-coa
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longa
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curcuminoids
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rhizome
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turmeric
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synthesis
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polyketide
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demethoxycurcumin
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bisdemethoxycurcumin
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ferulic
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4-coumarate
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zingiberaceae
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zedoaria
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condensing
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intraspecies
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caffeoyl-coa
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kwangsiensis
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3-hydroxylase
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analysis
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biofuel production
- 2.3.1.217
- curcuma
-
diketide-coa
- longa
-
curcuminoids
- rhizome
- turmeric
- synthesis
- polyketide
- demethoxycurcumin
- bisdemethoxycurcumin
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ferulic
- 4-coumarate
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zingiberaceae
- zedoaria
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condensing
-
intraspecies
- caffeoyl-coa
- kwangsiensis
-
3-hydroxylase
- analysis
- biofuel production
Reaction
Synonyms
curcumin synthase, curcumin synthase 1, curcumin synthase 2, CURS, CURS1, CURS2, CURS3, OsCUS, ZoCURS
ECTree
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Substrates Products
Substrates Products on EC 2.3.1.217 - curcumin synthase
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REACTION DIAGRAM
(4-coumaroyl)acetyl-CoA + 3-(4-hydroxyphenyl)propionyl-CoA + H2O
2 CoA + tetrahydrobisdemethoxycurcumin + CO2
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(4-coumaroyl)acetyl-CoA + feruloyl-CoA + H2O
demethoxycurcumin + CO2 + 2 CoA
preferred activity of CURS1, CURS2, and CURS3
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?
cinnamoyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O
CoA + dicinnamoylmethane + N-acetylcysteamine
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low activity
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?
feruloyl-CoA + 3-oxo-5-phenyl-4-pentenoic acid + H2O
CoA + cinnamoylferuloylmethane + CO2
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?
feruloyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O
CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
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?
feruloyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O
CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
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?
feruloyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O
CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
via 3-oxo-5-phenyl-4-pentenoic acid
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feruloyl-CoA + feruloylacetyl-CoA + H2O
2 CoA + curcumin + CO2
preferred activity of CURS1, CURS2, and CURS3
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?
feruloyl-CoA + feruloylacetyl-CoA + H2O
2 CoA + curcumin + CO2
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feruloyl-CoA is the preferred starter substrate
product identification by LC-ESI MS/MS
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?
feruloyl-CoA + feruloylacetyl-CoA + H2O
2 CoA + curcumin + CO2
two-step reaction of hydrolysis and decarboxylative condensation
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feruloyl-CoA + feruloylacetyl-CoA + H2O
2 CoA + curcumin + CO2
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CURS1 catalyzes the hydrolysis of diketide-CoA to yield a 2-oxoacid (ii) and decarboxylative condensation of the 2-oxoacid with feruloyl-CoA to yield curcumin
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additional information
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA, cf. EC 2.3.1.219. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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additional information
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA, cf. EC 2.3.1.219. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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additional information
?
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA, cf. EC 2.3.1.219. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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?
additional information
?
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA, cf. EC 2.3.1.219. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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?
additional information
?
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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-
?
additional information
?
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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-
?
additional information
?
-
substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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-
?
additional information
?
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substrate specificity, overview. CURS2 prefers feruloyl-CoA as a starter substrate, while CURS3 is equally active with both feruloyl-CoA and 4-coumaroyl-CoA. Thus, CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin
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additional information
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the enzyme can also convert diketide-CoA esters into 2-oxoacids and CoA, which are then converted into curcuminoids. For activity assays, cinnamoyl-CoA, 4-coumaroyl-CoA, or feruloyl-CoA are used as starter substrates and malonyl-CoA or cinnamoyl-diketide-N-acetylcysteamine as extender substrates, cf. EC 2.3.1.218 and EC 2.31.219
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additional information
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when diketide-CoA synthase (DCS) and curcumin synthase (ZoCURS) are co-incubated in the presence of 3-(4-hydroxyphenyl)propionyl-CoA and malonyl-CoA, tetrahydrobisdemethoxycurcumin and 4-hydroxybenzylacetone are produced
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