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Literature summary extracted from

  • Katsuyama, Y.; Matsuzawa, M.; Funa, N.; Horinouchi, S.
    In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa (2007), J. Biol. Chem., 282, 37702-37709.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.211 expression of the His-tagged enzyme in Escherichia coli strain BL21 (DE3) Oryza sativa

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.3.1.211 43000
-
 x * 43000, recombinant His-tagged enzyme, SDS-PAGE Oryza sativa

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.3.1.211 2 4-coumaroyl-CoA + malonyl-CoA + H2O Oryza sativa
-
 3 CoA + bisdemethoxycurcumin + 2 CO2
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.211 Oryza sativa Q8LIL0
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.211 recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3) Oryza sativa

Reaction

EC Number Reaction Comment Organism Reaction ID
2.3.1.211 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
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.211 2 4-coumaroyl-CoA + malonyl-CoA + H2O
-
 Oryza sativa 3 CoA + bisdemethoxycurcumin + 2 CO2
-
 ?
2.3.1.211 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 ?
2.3.1.211 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
-
 ?
2.3.1.211 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 ?
2.3.1.211 cinnamoyl-CoA + 3-oxo-octanoate + H2O
-
 Oryza sativa CoA + cinnamoyl(hexanoyl)methane + ?
-
 ?
2.3.1.211 cinnamoyl-CoA + 3-oxo-octanoyl-N-acetylcysteamine thioester + H2O
-
 Oryza sativa CoA + cinnamoyl(hexanoyl)methane + ?
-
 ?
2.3.1.211 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

EC Number Subunits Comment Organism
2.3.1.211 ? x * 43000, recombinant His-tagged enzyme, SDS-PAGE Oryza sativa

Synonyms

EC Number Synonyms Comment Organism
2.3.1.211 curcuminoid synthase
-
 Oryza sativa
2.3.1.211 CUS
-
 Oryza sativa

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.211 45
-
-
 Oryza sativa

Temperature Range [°C]

EC Number Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
2.3.1.211 25 60 activity range, profile overview Oryza sativa

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.211 6.5
-
-
 Oryza sativa

pH Range

EC Number pH Minimum pH Maximum Comment Organism
2.3.1.211 6 8 activity range, profile overview Oryza sativa

General Information

EC Number General Information Comment Organism
2.3.1.211 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