Cloned (Comment) | Organism |
---|---|
expression of the His-tagged enzyme in Escherichia coli strain BL21 (DE3) | Oryza sativa |
Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
---|---|---|---|
43000 | - |
x * 43000, recombinant His-tagged enzyme, SDS-PAGE | Oryza sativa |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
2 4-coumaroyl-CoA + malonyl-CoA + H2O | Oryza sativa | - |
3 CoA + bisdemethoxycurcumin + 2 CO2 | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Oryza sativa | Q8LIL0 | - |
- |
Purification (Comment) | Organism |
---|---|
recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3) | Oryza sativa |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
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 | Oryza sativa |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
2 4-coumaroyl-CoA + malonyl-CoA + H2O | - |
Oryza sativa | 3 CoA + bisdemethoxycurcumin + 2 CO2 | - |
? | |
2 4-coumaroyl-CoA + malonyl-CoA + H2O | - |
Oryza sativa | 3 CoA + bisdemethoxycurcumin + 2 CO2 | 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 | very low activity | Oryza sativa | 3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2H-pyran-2-one + curcumin | - |
? | |
cinnamoyl-CoA + 2 malonyl-CoA + H2O | - |
Oryza sativa | 3 CoA + 4-hydroxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one + 2 CO2 | cinnamoyl-CoA reacts to form a triketide pyrone with a small amount of dicinnamoylmethane | ? | |
cinnamoyl-CoA + 3-oxo-octanoate + H2O | - |
Oryza sativa | CoA + cinnamoyl(hexanoyl)methane + ? | - |
? | |
cinnamoyl-CoA + 3-oxo-octanoyl-N-acetylcysteamine thioester + H2O | - |
Oryza sativa | CoA + cinnamoyl(hexanoyl)methane + ? | - |
? | |
additional information | 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 | Oryza sativa | ? | - |
? |
Subunits | Comment | Organism |
---|---|---|
? | x * 43000, recombinant His-tagged enzyme, SDS-PAGE | Oryza sativa |
Synonyms | Comment | Organism |
---|---|---|
curcuminoid synthase | - |
Oryza sativa |
CUS | - |
Oryza sativa |
Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|
45 | - |
- |
Oryza sativa |
Temperature Minimum [°C] | Temperature Maximum [°C] | Comment | Organism |
---|---|---|---|
25 | 60 | activity range, profile overview | Oryza sativa |
pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|
6.5 | - |
- |
Oryza sativa |
pH Minimum | pH Maximum | Comment | Organism |
---|---|---|---|
6 | 8 | activity range, profile overview | Oryza sativa |
General Information | Comment | Organism |
---|---|---|
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 | Oryza sativa |