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Literature summary extracted from

  • Koeduka, T.; Louie, G.V.; Orlova, I.; Kish, C.M.; Ibdah, M.; Wilkerson, C.G.; Bowman, M.E.; Baiga, T.J.; Noel, J.P.; Dudareva, N.; Pichersky, E.
    The multiple phenylpropene synthases in both Clarkia breweri and Petunia hybrida represent two distinct protein lineages (2008), Plant J., 54, 362-374.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.318 DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis Petunia x hybrida
1.1.1.318 DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, expression of nontagged and of His-tagged CbEGS1 and CbEGS2 in Escherichia coli Clarkia breweri
1.1.1.319 DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis Petunia x hybrida
1.1.1.319 DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, expression in Escherichia coli Clarkia breweri

Protein Variants

EC Number Protein Variants Comment Organism
1.1.1.318 F84V/I87Y site-directed mutagenesis, the CbEGS1 mutant plants show increased isoeugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.318 F86V/I89Y site-directed mutagenesis, the CbEGS2 mutant plants show increased isoeugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.318 Q86V/L89Y site-directed mutagenesis, the mutant plants show increased isoeugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Petunia x hybrida
1.1.1.319 L91I/L92H/D95N site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 R73K/V77I/S83P/V84F site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 R73K/V77I/S83P/V84F/Y87I/P88S/L91I/L92H/D95N site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 S83P/V84F site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 S83P/V84F/Y87I/P88S site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 V84F site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 V84F/Y87I site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 V88F/Y91I site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Petunia x hybrida
1.1.1.319 Y87I site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri
1.1.1.319 Y87I/P88S site-directed mutagenesis, the mutant plants show increased eugenol production and an altered eugenol/isoeugenol ratio compared to the wild-type enzyme Clarkia breweri

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.318 0.0933
-
 coniferyl acetate CbEGS1, pH 6.5, 28°C Clarkia breweri
1.1.1.318 0.2453
-
 coniferyl acetate PhEGS1, pH 6.5, 28°C Petunia x hybrida
1.1.1.318 0.3105
-
 coniferyl acetate CbEGS2, pH 6.5, 28°C Clarkia breweri
1.1.1.319 0.2115
-
 coniferyl acetate CbIGS1, pH 6.5, 28°C Clarkia breweri
1.1.1.319 0.2261
-
 coniferyl acetate PhIGS1, pH 6.5, 28°C Petunia x hybrida

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.1.1.318 36000
-
 x * 38000, recombinant nontagged CbEGS2, SDS-PAGE, x * 36000, recombinant nontagged CbEGS1, SDS-PAGE Clarkia breweri
1.1.1.318 38000
-
 x * 38000, recombinant nontagged CbEGS2, SDS-PAGE, x * 36000, recombinant nontagged CbEGS1, SDS-PAGE Clarkia breweri

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.318 coniferyl acetate + NADPH + H+ Ocimum basilicum
-
 eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+ Clarkia breweri
-
 eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+ Petunia x hybrida PhEGS1 converts coniferyl acetate to eugenol eugenol + acetate + NADP+
-
 ?
1.1.1.319 coniferyl acetate + NADPH + H+ Petunia x hybrida
-
 isoeugenol + acetate + NADP+
-
 ?
1.1.1.319 coniferyl acetate + NADPH + H+ Clarkia breweri
-
 isoeugenol + acetate + NADP+
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.318 Clarkia breweri
-
-
-
1.1.1.318 Ocimum basilicum
-
-
-
1.1.1.318 Petunia x hybrida
-
 cv. Mitchell
-
1.1.1.319 Clarkia breweri
-
-
-
1.1.1.319 Petunia x hybrida
-
 cv. Mitchell
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.318 native EGS 118fold from petals by alternating steps of anion exchange and hydrophobic interaction chromatography, co-purification with isoeugenol synthase, EC 1.1.1.319. Recombinant His-tagged CbEGS1 and CbEGS2 from Escherichia coli by nickel affinity chromatography Clarkia breweri
1.1.1.319 native enzyme 9.2fold from petals by alternating steps of anion exchange and hydrophobic interaction chromatography, co-purification with eugenol synthase, EC 1.1.1.318. Recombinant His-tagged CbIGS from Escherichia coli by nickel affinity chromatography Clarkia breweri

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.1.1.318 flower
-
 Ocimum basilicum
-
1.1.1.318 flower PhEGS1 is expressed specifically in the scent-producing parts of the flowers, limbs and tube, but not in other parts of the flowers nor in leaves Petunia x hybrida
-
1.1.1.318 flower the highest specific activity levels of eugenol synthase are found in the stamens, followed closely by the pistil and petals Clarkia breweri
-
1.1.1.318 petal
-
 Clarkia breweri
-
1.1.1.318 pistil
-
 Clarkia breweri
-
1.1.1.318 stamen
-
 Clarkia breweri
-
1.1.1.319 flower
-
 Petunia x hybrida
-
1.1.1.319 flower the highest specific activity levels of eugenol synthase are found in the stamens, followed closely by the pistil and petals Clarkia breweri
-
1.1.1.319 petal
-
 Clarkia breweri
-
1.1.1.319 pistil
-
 Clarkia breweri
-
1.1.1.319 stamen
-
 Clarkia breweri
-

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.1.1.318 1.98
-
 purified native, wild-type CbEGS, pH 6.5, 28°C Clarkia breweri
1.1.1.319 0.65
-
 purified native, wild-type CbIGS1, pH 6.5, 28°C Clarkia breweri

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.318 coniferyl acetate + NADPH + H+
-
 Ocimum basilicum eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+
-
 Petunia x hybrida eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+
-
 Clarkia breweri eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+ PhEGS1 converts coniferyl acetate to eugenol Petunia x hybrida eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+ CbEGS1 is specific for isoeugenol production Clarkia breweri eugenol + acetate + NADP+
-
 ?
1.1.1.318 coniferyl acetate + NADPH + H+ ObEGS1 uses a quinone methide intermediate-based mechanism to generate an intermediate to which the reductive transfer of the reducing hydride can then be easily accomplished. the enzyme acts on the substrate via a push-pull mechanism, removing the proton of the para hydroxyl group and promoting the cleavage of the acetyl group. In the resultant quinone-methide intermediate, the C7 atom serves as the acceptor of the hydride ion from NADPH Ocimum basilicum eugenol + acetate + NADP+
-
 ?
1.1.1.319 coniferyl acetate + NADPH + H+
-
 Petunia x hybrida isoeugenol + acetate + NADP+
-
 ?
1.1.1.319 coniferyl acetate + NADPH + H+
-
 Clarkia breweri isoeugenol + acetate + NADP+
-
 ?
1.1.1.319 coniferyl acetate + NADPH + H+ CbIGS1 is specific for isoeugenol production Clarkia breweri isoeugenol + acetate + NADP+
-
 ?
1.1.1.319 coniferyl acetate + NADPH + H+ PhIGS1 uses a quinone methide intermediate-based mechanism to generate an intermediate to which the reductive transfer of the reducing hydride can then be easily accomplished Petunia x hybrida isoeugenol + acetate + NADP+
-
 ?
1.1.1.319 additional information the position of the substrate in the active site of PhIGS1 is such that the hydride is transferred to C9 instead of C7, as occurs in Ocimum basilicum eugenol synthase, EC 1.1.1.318 Petunia x hybrida ?
-
 ?

Subunits

EC Number Subunits Comment Organism
1.1.1.318 ? x * 38000, recombinant nontagged CbEGS2, SDS-PAGE, x * 36000, recombinant nontagged CbEGS1, SDS-PAGE Clarkia breweri

Synonyms

EC Number Synonyms Comment Organism
1.1.1.318 CbEGS1
-
 Clarkia breweri
1.1.1.318 CbEGS2
-
 Clarkia breweri
1.1.1.318 EGS
-
 Ocimum basilicum
1.1.1.318 EGS
-
 Petunia x hybrida
1.1.1.318 EGS
-
 Clarkia breweri
1.1.1.318 ObEGS1
-
 Ocimum basilicum
1.1.1.318 PhEGS1
-
 Petunia x hybrida
1.1.1.319 CbIGS1
-
 Clarkia breweri
1.1.1.319 PhIGS1
-
 Petunia x hybrida

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.318 28
-
 assay at Petunia x hybrida
1.1.1.318 28
-
 assay at Clarkia breweri
1.1.1.319 28
-
 assay at Petunia x hybrida
1.1.1.319 28
-
 assay at Clarkia breweri

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.1.1.318 0.25
-
 coniferyl acetate CbEGS2, pH 6.5, 28°C Clarkia breweri
1.1.1.318 0.26
-
 coniferyl acetate CbEGS1, pH 6.5, 28°C Clarkia breweri
1.1.1.318 0.6
-
 coniferyl acetate PhEGS1, pH 6.5, 28°C Petunia x hybrida
1.1.1.319 0.99
-
 coniferyl acetate CbIGS1, pH 6.5, 28°C Clarkia breweri
1.1.1.319 1.3
-
 coniferyl acetate PhIGS1, pH 6.5, 28°C Petunia x hybrida

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.318 6.5
-
 assay at Petunia x hybrida
1.1.1.318 6.5
-
 assay at Clarkia breweri
1.1.1.319 6.5
-
 assay at Petunia x hybrida
1.1.1.319 6.5
-
 assay at Clarkia breweri

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.318 NADPH
-
 Petunia x hybrida
1.1.1.318 NADPH
-
 Clarkia breweri
1.1.1.319 NADPH
-
 Petunia x hybrida
1.1.1.319 NADPH
-
 Clarkia breweri

General Information

EC Number General Information Comment Organism
1.1.1.318 physiological function plants synthesize the volatile phenylpropene compounds eugenol and isoeugenol to serve in defense against herbivores and pathogens and to attract pollinators. Clarkia breweri flowers emit a mixture of eugenol and isoeugenol. Eugenol and isoeugenol differ in the position of the double bond in the propene side chain Clarkia breweri
1.1.1.318 physiological function plants synthesize the volatile phenylpropene compounds eugenol and isoeugenol to serve in defense against herbivores and pathogens and to attract pollinators. Petunia hybrida flowers emit mostly isoeugenol with small amounts of eugenol. Eugenol and isoeugenol differ in the position of the double bond in the propene side chain Petunia x hybrida
1.1.1.319 physiological function plants synthesize the volatile phenylpropene compounds eugenol and isoeugenol to serve in defense against herbivores and pathogens and to attract pollinators. Clarkia breweri flowers emit a mixture of eugenol and isoeugenol. Eugenol and isoeugenol differ in the position of the double bond in the propene side chain Clarkia breweri
1.1.1.319 physiological function plants synthesize the volatile phenylpropene compounds eugenol and isoeugenol to serve in defense against herbivores and pathogens and to attract pollinators. Petunia hybrida flowers emit mostly isoeugenol with small amounts of eugenol. Eugenol and isoeugenol differ in the position of the double bond in the propene side chain Petunia x hybrida

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.1.1.318 0.8
-
 coniferyl acetate CbEGS2, pH 6.5, 28°C Clarkia breweri
1.1.1.318 2.4
-
 coniferyl acetate PhEGS1, pH 6.5, 28°C Petunia x hybrida
1.1.1.318 2.8
-
 coniferyl acetate CbEGS1, pH 6.5, 28°C Clarkia breweri
1.1.1.319 4.7
-
 coniferyl acetate CbIGS1, pH 6.5, 28°C Clarkia breweri
1.1.1.319 5.7
-
 coniferyl acetate PhIGS1, pH 6.5, 28°C Petunia x hybrida