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Literature summary for 2.3.1.217 extracted from

  • Katsuyama, Y.; Miyazono, K.; Tanokura, M.; Ohnishi, Y.; Horinouchi, S.
    Structural and biochemical elucidation of mechanism for decarboxylative condensation of beta-keto acid by curcumin synthase (2011), J. Biol. Chem., 286, 6659-6668.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.3.1.217

Cloned(Commentary)

Cloned (Comment) Organism
expression of His4-tagged CURS1 in Escherichia coli strain BL21(DE3) Curcuma longa

Crystallization (Commentary)

Crystallization (Comment) Organism
purified recombinant His4-tagged CURS1, sitting drop vapor diffusion method, mixing of 10 mg/ml protein in 10 mM Tris-HCl, pH 8.0, 10% glycerol, and 1 mM tris(2-carboxyethyl)phosphine with reservoir solution containing 0.3 M sodium malonate, pH 7.0, and 25% PEG3350, X-ray diffraction structure determination and analysis at 2.32 A resolution, modeling Curcuma longa

Protein Variants

Protein Variants Comment Organism
G211F site-directed mutagenesis, the mutant shows highly reduced 2-oxoacid condensation activity compared to the wild-type enzyme Curcuma longa
H303A site-directed mutagenesis, active site residue mutant, the mutant shows reduced 2-oxoacid condensation activity compared to the wild-type enzyme Curcuma longa
H303Q site-directed mutagenesis, active site residue mutant, the mutant shows reduced 2-oxoacid condensation activity compared to the wild-type enzyme Curcuma longa

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0012
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant mutant H303Q Curcuma longa
0.0017
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant wild-type enzyme Curcuma longa
0.003
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant mutant H303Q Curcuma longa
0.0059
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant wild-type enzyme Curcuma longa
0.113
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant mutant G211F Curcuma longa
0.138
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant mutant G211F Curcuma longa

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
feruloyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O Curcuma longa
-
 CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
-
 ?
feruloyl-CoA + feruloylacetyl-CoA + H2O Curcuma longa
-
 2 CoA + curcumin + CO2
-
 ?
additional information Curcuma longa 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 ?
-
 ?

Organism

Organism UniProt Comment Textmining
Curcuma longa C0SVZ6
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His4-tagged CURS1 from Escherichia coli strain BL21(DE3) by nickel affinity and anion exchange chromatography, followed by ultrafiltration Curcuma longa

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
feruloyl-CoA + 3-oxo-5-phenyl-4-pentenoic acid + H2O
-
 Curcuma longa CoA + cinnamoylferuloylmethane + CO2
-
 ?
feruloyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O
-
 Curcuma longa CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
-
 ?
feruloyl-CoA + cinnamoyl-diketide-N-acetylcysteamine + H2O via 3-oxo-5-phenyl-4-pentenoic acid Curcuma longa CoA + cinnamoylferuloylmethane + N-acetylcysteamine + CO2
-
 ?
feruloyl-CoA + feruloylacetyl-CoA + H2O
-
 Curcuma longa 2 CoA + curcumin + CO2
-
 ?
feruloyl-CoA + feruloylacetyl-CoA + H2O two-step reaction of hydrolysis and decarboxylative condensation Curcuma longa 2 CoA + curcumin + CO2
-
 ?
additional information 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 Curcuma longa ?
-
 ?

Synonyms

Synonyms Comment Organism
curcumin synthase 1
-
 Curcuma longa
CURS1
-
 Curcuma longa

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Curcuma longa

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.00007
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant mutant H303Q Curcuma longa
0.0015
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant mutant G211F Curcuma longa
0.0017
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant mutant H303Q Curcuma longa
0.0043
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant wild-type enzyme Curcuma longa
0.0083
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant mutant G211F Curcuma longa
0.125
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant wild-type enzyme Curcuma longa

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5 8 assay at Curcuma longa

General Information

General Information Comment Organism
evolution the enzyme belongs to the Type III polyketide synthase family Curcuma longa
metabolism the enzyme catalyzes a step in the curcuminoid biosynthesis, pathway overview Curcuma longa
additional information active site residue His303 is important for 2-oxoacid condensation, involvement of the hydrophobic cavity around Phe265 in 2-oxoacid condensation, wild-type and mutant ligand binding structures and structure-function relationship, modeling, overview Curcuma longa

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.013
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant mutant G211F Curcuma longa
0.024
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant mutant H303Q Curcuma longa
0.112
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant mutant G211F Curcuma longa
1.605
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant mutant H303Q Curcuma longa
2.915
-
 cinnamoyl-diketide-N-acetylcysteamine pH 7.5, 37°C, recombinant wild-type enzyme Curcuma longa
20.54
-
 3-oxo-5-phenyl-4-pentenoic acid pH 7.5, 37°C, recombinant wild-type enzyme Curcuma longa