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Information on EC 1.1.1.318 - eugenol synthase
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EC Tree
1.1.1.318 eugenol synthaseIUBMB Comments
The enzyme acts in the opposite direction. The enzymes from the plants Ocimum basilicum (sweet basil) [1,3], Clarkia breweri and Petunia hybrida only accept coniferyl acetate and form eugenol. The enzyme from Pimpinella anisum (anise) forms anol (from 4-coumaryl acetate) in vivo, although the recombinant enzyme can form eugenol from coniferyl acetate . The enzyme from Larrea tridentata (creosote bush) also forms chavicol from a coumaryl ester and can use NADH .
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Word Map
- 1.1.1.318
-
phenylpropene
-
phenylpropanoids
- ocimum
- basilicum
-
scent
-
emit
- petunia
- basil
-
o-methyltransferase
- hybrida
-
floral
-
cinnamyl
- methyleugenol
- petals
-
ripe
-
pollinator
-
benzenoid
-
trichomes
-
ammonia-lyase
- strawberry
-
peltate
- estragole
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
eugenol synthase, rcegs1, obegs4, obegs1, dce(i)gs1, eugenol synthase 1, cbegs1, cbegs2, chavicol/eugenol synthase, eugenol/isoeugenol synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
EGS
EGS1
EGS2
eugenol synthase 1
LtCES1
ObEGS1
EGS1
-
-
-
-
EGS2
-
-
-
-
LtCES1
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH + H+
-
-
-
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eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH + H+
reaction mechanism, overview
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH + H+
reaction mechanism, detailed overview
-
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH + H+
eugenol synthase catalyzes the reductive displacement of acetate from the propenyl side chain of the substrate coniferyl acetate to produce the allyl-phenylpropene eugenol, two-step reaction mechanism involving the formation of a quinone-methide prior to reduction, overview. The formation of this intermediate is promoted by a hydrogen-bonding network that favors deprotonation of the substrate's 4-hydroxyl group and disfavors binding of the acetate moiety, akin to a push-pull catalytic mechanism, involvement of a quinone-methide, a conjugated enone, intermediate in the bond cleavage
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
eugenol:NADP+ oxidoreductase (coniferyl ester reducing)
The enzyme acts in the opposite direction. The enzymes from the plants Ocimum basilicum (sweet basil) [1,3], Clarkia breweri and Petunia hybrida [4] only accept coniferyl acetate and form eugenol. The enzyme from Pimpinella anisum (anise) forms anol (from 4-coumaryl acetate) in vivo, although the recombinant enzyme can form eugenol from coniferyl acetate [5]. The enzyme from Larrea tridentata (creosote bush) also forms chavicol from a coumaryl ester and can use NADH [2].
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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+
-
-
-
r
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
-
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
-
-
-
?
4-coumaryl acetate + NADPH + H+
chavicol + acetate + NADP+
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-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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CbEGS1 is specific for isoeugenol production
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
GC-MS analysis product analysis
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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GC-MS analysis product analysis
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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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
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-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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reaction via a quinone methide-like intermediate
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-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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PhEGS1 converts coniferyl acetate to eugenol
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-
?
additional information
?
-
purified recombinant DcE(I)GS1 catalyzes the formation of eugenol (70% of total products, EC 1.1.1.318), as well as isoeugenol (30% of total products,, EC 1.1.1.319) from coniferyl acetate
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-
-
additional information
?
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Gymnadenia odoratissima proteins synthesize eugenol only
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?
additional information
?
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Gymnadenia odoratissima proteins synthesize eugenol only
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?
additional information
?
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Gymnadenia odoratissima proteins synthesize eugenol only
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?
additional information
?
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Gymnadenia densiflora proteins synthesize eugenol, as well as a smaller amount of isoeugenol
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?
additional information
?
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Gymnadenia densiflora proteins synthesize eugenol, as well as a smaller amount of isoeugenol
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?
additional information
?
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Gymnadenia densiflora proteins synthesize eugenol, as well as a smaller amount of isoeugenol
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?
additional information
?
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specificity of EGS for the production of allyl phenols in heterologically EGS expressing Fragaria x ananassa fruits
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?
additional information
?
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determinants of the regioselectivity of the EGS-catalyzed reduction reaction, overview
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?
additional information
?
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determinants of the regioselectivity of the EGS-catalyzed reduction reaction, overview
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?
additional information
?
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no substrate: 4-coumaryl acetate, cinnamyl acetate
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?
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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-
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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-
-
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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-
-
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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-
-
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
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GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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-
additional information
?
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no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
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additional information
?
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no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
-
no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
-
no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
-
no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
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no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
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no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
-
no activity with 4-coumaryl acetate. GC-MS analysis of products formed in Escherichia coli recombinantly expressing ObEGS isozymes
-
-
-
additional information
?
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no substrate: cinnamyl acetate
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?
additional information
?
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no substrate: cinnamyl acetate
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?
additional information
?
-
no substrate: cinnamyl acetate
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
specificity of EGS for the production of allyl phenols in heterologically EGS expressing Fragaria x ananassa fruits
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
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-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
r
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
-
-
-
?
coniferyl acetate + NADPH + H+
eugenol + acetate + NADP+
-
PhEGS1 converts coniferyl acetate to eugenol
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADP+
-
NADPH
-
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(7S,8S)-ethyl (7,8-methylene)-dihydroferulate
EMDF, a mixed competitive inhibitor, chemical synthesis, and enzyme binding structure, overview. Key interactions between EMDF and the EGS holoenzyme include stacking of the phenyl ring of EMDF against the cofactor's nicotinamide ring and a water-mediated hydrogen-bonding interaction between the EMDF 4-hydroxy group and the side-chain amino moiety of a conserved lysine residue, Lys132
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
28
30
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.1
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
brenda