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4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
cinnamyl acetate + NADPH + H+
? + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
additional information
?
-
4-coumaryl acetate + NADPH + H+

chavicol + acetate + NADP+
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-
GC-MS analysis product analysis
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+

eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
CbEGS1 is specific for isoeugenol production
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
GC-MS analysis product analysis
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
GC-MS analysis product analysis
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
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
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
reaction via a quinone methide-like intermediate
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
PhEGS1 converts coniferyl acetate to eugenol
-
?
additional information

?
-
Gymnadenia odoratissima proteins synthesize eugenol only
-
?
additional information
?
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Gymnadenia odoratissima proteins synthesize eugenol only
-
?
additional information
?
-
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Gymnadenia odoratissima proteins synthesize eugenol only
-
?
additional information
?
-
Gymnadenia densiflora proteins synthesize eugenol, as well as a smaller amount of isoeugenol
-
?
additional information
?
-
Gymnadenia densiflora proteins synthesize eugenol, as well as a smaller amount of isoeugenol
-
?
additional information
?
-
-
Gymnadenia densiflora proteins synthesize eugenol, as well as a smaller amount of isoeugenol
-
?
additional information
?
-
specificity of EGS for the production of allyl phenols in heterologically EGS expressing Fragaria x ananassa fruits
-
?
additional information
?
-
determinants of the regioselectivity of the EGS-catalyzed reduction reaction, overview
-
?
additional information
?
-
-
determinants of the regioselectivity of the EGS-catalyzed reduction reaction, overview
-
?
additional information
?
-
no substrate: 4-coumaryl acetate, cinnamyl acetate
-
?
additional information
?
-
no substrate: cinnamyl acetate
-
?
additional information
?
-
no substrate: cinnamyl acetate
-
?
additional information
?
-
no substrate: cinnamyl acetate
-
?
additional information
?
-
-
no substrate: cinnamyl acetate
-
?
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4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
additional information
?
-
specificity of EGS for the production of allyl phenols in heterologically EGS expressing Fragaria x ananassa fruits
-
-
?
4-coumaryl acetate + NADPH + H+

chavicol + acetate + NADP+
-
-
-
-
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+

eugenol + acetate + NADP+
-
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
PhEGS1 converts coniferyl acetate to eugenol
-
-
?
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the highest specific activity levels of eugenol synthase are found in the stamens, followed closely by the pistil and petals
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expression in floral tissue
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expression in floral tissue
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-
-
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higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
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higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
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higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
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higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
brenda
-
-
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-
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
brenda
-
-
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higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
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higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
brenda
higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
brenda
higher transcript levels especially in young leaves and inflorescence, levels are positively correlated with eugenol contents
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additional information

no expression in leaf tissue
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additional information
no expression in leaf tissue
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additional information
-
no expression in leaf tissue
brenda
additional information
no expression in leaf tissue
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additional information
no expression in leaf tissue
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additional information
-
no expression in leaf tissue
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metabolism
the enzyme is involved in the biosynthesis of phenylpropenes, overview
evolution

EGS is structurally related to the shortchain dehydrogenase/reductases, SDRs, and in particular, enzymes in the isoflavone-reductase-like subfamily
evolution
the phenylpropene-forming eugenol synthase, EGS, belongs to a structural family of NADPH-dependent reductases that also includes isoeugenol synthase, IGS, pinoresinol-lariciresinol reductase, isoflavone reductase, and phenylcoumaran benzylic ether reductase, evolution and function of EGS1 and IGS1, overview
physiological function

catalytic involvement in EGS of the conserved Lys132 in preparing the phenolic substrate for quinone methide formation through the proton-relay network
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
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
physiological function
introduction of petunia coniferyl alcohol acetyltransferase (CFAT) and eugenol synthase (EGS) into hybrid aspen. The overexpression of EGS alone results in a subtle increase in either eugenol or eugenol glycosides, and the overexpression of both CFAT and EGS results in significant increases in the levels of both eugenol and eugenol glycosides which are nonetheless lower than the increases seen with overexpression of CFAT alone
additional information

structure of a ternary complex of EGS bound to the cofactor NADP(H) and a mixed competitive inhibitor (7S,8S)-ethyl (7,8-methylene)-dihydroferulate, binding interactions within the EGS active site, overview
additional information
-
structure of a ternary complex of EGS bound to the cofactor NADP(H) and a mixed competitive inhibitor (7S,8S)-ethyl (7,8-methylene)-dihydroferulate, binding interactions within the EGS active site, overview
additional information
-
the enzyme is a PIP reductase homologue
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Vassao, D.; Kim, S.; Milhollan, J.; Eichinger, D.; Davin, L.; Lewis, N.
A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeug
Arch. Biochem. Biophys.
465
209-218
2007
Larrea tridentata
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Hoffmann, T.; Kurtzer, R.; Skowranek, K.; Kiessling, P.; Fridman, E.; Pichersky, E.; Schwab, W.
Metabolic engineering in strawberry fruit uncovers a dormant biosynthetic pathway
Metab. Eng.
13
527-531
2011
Ocimum basilicum (Q15GI4)
brenda
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
Plant J.
54
362-374
2008
Clarkia breweri, Ocimum basilicum, Petunia x hybrida
brenda
Koeduka, T.; Orlova, I.; Baiga, T.J.; Noel, J.P.; Dudareva, N.; Pichersky, E.
The lack of floral synthesis and emission of isoeugenol in Petunia axillaris subsp. parodii is due to a mutation in the isoeugenol synthase gene
Plant J.
58
961-969
2009
Petunia axillaris subsp. parodii
brenda
Louie, G.V.; Baiga, T.J.; Bowman, M.E.; Koeduka, T.; Taylor, J.H.; Spassova, S.M.; Pichersky, E.; Noel, J.P.
Structure and reaction mechanism of basil eugenol synthase
PLoS ONE
2
e993
2007
Ocimum basilicum (Q15GI4), Ocimum basilicum
brenda
Koeduka, T.; Fridman, E.; Gang, D.; Vassao, D.; Jackson, B.; Kish, C.; Orlova, I.; Spassova, S.; Lewis, N.; Noel, J.; Baiga, T.; Dudareva, N.; Pichersky, E.
Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester
Proc. Natl. Acad. Sci. USA
103
10128-10133
2006
Ocimum basilicum (Q15GI4)
brenda
Koeduka, T.; Suzuki, S.; Iijima, Y.; Ohnishi, T.; Suzuki, H.; Watanabe, B.; Shibata, D.; Umezawa, T.; Pichersky, E.; Hiratake, J.
Enhancement of production of eugenol and its glycosides in transgenic aspen plants via genetic engineering
Biochem. Biophys. Res. Commun.
436
73-78
2013
Petunia x hybrida (B2WSN1)
brenda
Anand, A.; Jayaramaiah, R.H.; Beedkar, S.D.; Singh, P.A.; Joshi, R.S.; Mulani, F.A.; Dholakia, B.B.; Punekar, S.A.; Gade, W.N.; Thulasiram, H.V.; Giri, A.P.
Comparative functional characterization of eugenol synthase from four different Ocimum species: Implications on eugenol accumulation
Biochim. Biophys. Acta
1864
1539-1547
2016
Ocimum basilicum (A0A1B2U6R8), Ocimum tenuiflorum (A0A1B2U6S6), Ocimum tenuiflorum, Ocimum gratissimum (A0A1B2U6S7), Ocimum kilimandscharicum (A0A1B2U6T4)
brenda
Gupta, A.K.; Schauvinhold, I.; Pichersky, E.; Schiestl, F.P.
Eugenol synthase genes in floral scent variation in Gymnadenia species
Funct. Integr. Genomics
14
779-788
2014
Gymnadenia x densiflora (A0A0E3H852), Gymnadenia x densiflora (A0A0E3KNP5), Gymnadenia x densiflora, Gymnadenia odoratissima (A0A0E3NBN0), Gymnadenia odoratissima (A0A0E3NCN9), Gymnadenia odoratissima
brenda
Medina-Puche, L.; Molina-Hidalgo, F.J.; Boersma, M.; Schuurink, R.C.; Lopez-Vidriero, I.; Solano, R.; Franco-Zorrilla, J.M.; Caballero, J.L.; Blanco-Portales, R.; Munoz-Blanco, J.
An R2R3-MYB transcription factor regulates eugenol production in ripe strawberry fruit receptacles
Plant Physiol.
168
598-614
2015
Fragaria x ananassa (T2AZ69), Fragaria x ananassa
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