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Information on EC 2.1.1.146 - (iso)eugenol O-methyltransferase
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EC Tree
2.1.1.146 (iso)eugenol O-methyltransferaseIUBMB Comments
Acts on eugenol and chavicol as well as isoeugenol.
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Word Map
- 2.1.1.146
- breweri
-
clarkia
-
caffeic
-
ocimum
-
phenylpropene
- methyleugenol
-
phenylpropanoids
- basil
-
floral
-
scent
- basilicum
- trichomes
- flower
-
peltate
- monolignols
- lignin
-
glandular
- petal
-
coniferyl
-
para-hydroxyls
- aroma
-
onagraceae
-
o-methylation
-
chemotype
-
regiospecificity
-
emit
- california
-
etherifying
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
aimt1, chavicol o-methyltransferase, eugenol o-methyltransferase, rcomt1, (iso)eugenol o-methyltransferase, monolignol 4-o-methyltransferase, momt5, s-adenosyl-l-methionine:(iso)eugenol o-methyltransferase, isoeugenol-o-methyltransferase, eugenol-o-methyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(iso)eugenol O-methyltransferase
-
-
-
-
allylphenol O-methyltransferase
-
-
-
-
chavicol O-methyltransferase
-
-
-
-
EOMT
eugenol methyltransferase
-
-
-
-
eugenol O-methyltransferase
-
-
-
-
IEMT
isoeugenol methyltransferase
-
-
-
-
methyltransferase, (iso)eugenol
-
-
-
-
methyltransferase, allylphenol O-
-
-
-
-
S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase
-
-
-
-
EOMT
-
-
-
-
IEMT
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + isoeugenol = S-adenosyl-L-homocysteine + isomethyleugenol
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
methyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:isoeugenol O-methyltransferase
Acts on eugenol and chavicol as well as isoeugenol.
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CAS REGISTRY NUMBER
COMMENTARY
191744-33-9
-
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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
S-adenosyl-L-methionine + 2-methoxy-4-methylphenol
S-adenosyl-L-homocysteine + 1,2-dimethoxy-4-methylbenzene
-
16.8% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + 2-methoxyphenol
S-adenosyl-L-homocysteine + ?
-
4% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + 5-methoxyeugenol
S-adenosyl-L-homocysteine + ?
-
about 18% of the activity with isoeugenol
-
-
?
S-adenosyl-L-methionine + caffeyl alcohol
S-adenosyl-L-homocysteine + 4-methoxycaffeyl alcohol
-
-
-
?
S-adenosyl-L-methionine + chavicol
S-adenosyl-L-homocysteine + estragol
24% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + coniferyl alcohol
S-adenosyl-L-homocysteine + 4-methoxyconiferyl alcohol
-
-
-
?
S-adenosyl-L-methionine + coumaryl alcohol
S-adenosyl-L-homocysteine + 4-methoxycoumaryl alcohol
-
-
-
?
S-adenosyl-L-methionine + dihydrochavicol
S-adenosyl-L-homocysteine + ?
-
about 23% of the activity with isoeugenol
-
-
?
S-adenosyl-L-methionine + dihydroeugenol
S-adenosyl-L-homocysteine + methyldihydroeugenol
-
about 50% of the activity with isoeugenol
-
-
?
S-adenosyl-L-methionine + guaiacol
S-adenosyl-L-homocysteine + 1,2-dimethoxybenzene
29.9% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + monolignol
S-adenosyl-L-homocysteine + 4-O-methylmonolignol
-
-
-
?
S-adenosyl-L-methionine + sinapyl alcohol
S-adenosyl-L-homocysteine + 4-methoxysinapyl alcohol
-
-
-
?
S-adenosyl-L-methionine + t-anol
S-adenosyl-L-homocysteine + t-anethole
-
methylation of the p-OH group. 45% of the rate with isoeugenol
-
-
?
S-adenosyl-L-methionine + trans-isoeugenol
S-adenosyl-L-homocysteine + (E)-2',3'-dimethoxy-1-propenylbenzene
-
-
-
?
S-adenosyl-L-methionine + zingerone
S-adenosyl-L-homocysteine + 4-(3,4-dimethoxyphenyl)-butan-2-one
-
26.8% of the activity with eugenol
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
-
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
the enzyme is involved in the production of the floral volatile compounds methyleugenol and methylisoeugenol
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
-
-
?
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
-
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
-
-
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
26% of the activity with eugenol
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
-
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
-
-
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
-
the enzyme is involved in the production of the floral volatile compounds methyleugenol and methylisoeugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
-
methylation of the p-OH group
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
-
75% of the activity with eugenol
-
-
?
additional information
?
-
substrate specificities of engineered monolignol 4-O-methyltransferases, MOMT3, MOMT4, MOMT5, MOMT8, and MOMT9
-
-
-
additional information
?
-
-
no substrate: chavicol, eugenol, guaiacol, caffeic acid, 2-propylphenol
-
-
?
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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
S-adenosyl-L-methionine + eugenol
S-adenosyl-L-homocysteine + methyleugenol
-
the enzyme is involved in the production of the floral volatile compounds methyleugenol and methylisoeugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + methylisoeugenol
-
the enzyme is involved in the production of the floral volatile compounds methyleugenol and methylisoeugenol
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
-
-
-
-
?
S-adenosyl-L-methionine + isoeugenol
S-adenosyl-L-homocysteine + isomethyleugenol
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0114
coniferyl alcohol
pH 7.5, 30°C, recombinant enzyme mutant MOMT5
0.0161
coniferyl alcohol
pH 7.5, 30°C, recombinant enzyme mutant MOMT8
0.0161
coniferyl alcohol
pH 7.5, 30°C, recombinant enzyme mutant MOMT9
0.1926
coniferyl alcohol
pH 7.5, 30°C, recombinant enzyme mutant MOMT4
0.1985
coniferyl alcohol
pH 7.5, 30°C, recombinant enzyme mutant MOMT3
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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
0.0514
enzyme variant MOMT8, pH 7.5, 30°C, substrate coniferyl alcohol
0.0668
enzyme variant MOMT4, pH 7.5, 30°C, substrate coniferyl alcohol
0.0683
enzyme variant MOMT9, pH 7.5, 30°C, substrate coniferyl alcohol
0.0806
enzyme variant MOMT5, pH 7.5, 30°C, substrate coniferyl alcohol
0.3463
enzyme variant MOMT3, pH 7.5, 30°C, substrate coniferyl alcohol
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
expression throughout the plant with highest level in developing fruit
brenda
additional information
-
expression throughout the plant with highest level in developing fruit
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
homology modeling and substrate docking analysis of enzyme mutant MOMT8, substrate binding in crystal structures of MOMTs, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). CVMT1_OCIBA
356
0
39916
Swiss-Prot
other Location (Reliability: 3)
EOMT1_OCIBA
357
0
40237
Swiss-Prot
other Location (Reliability: 4)
IEMT_CLABR
368
0
39993
Swiss-Prot
other Location (Reliability: 2)
OMT1_SORBI
376
0
40847
Swiss-Prot
other Location (Reliability: 2)
B9RW39_RICCO
351
0
38956
TrEMBL
other Location (Reliability: 3)
B9SGP0_RICCO
356
0
39868
TrEMBL
other Location (Reliability: 3)
B9RVR2_RICCO
175
0
19973
TrEMBL
other Location (Reliability: 4)
B9SGP3_RICCO
127
0
13881
TrEMBL
other Location (Reliability: 5)
A0A4D6DKF2_9LAMI
335
0
37639
TrEMBL
Secretory Pathway (Reliability: 5)
B9RGB0_RICCO
360
0
39427
TrEMBL
other Location (Reliability: 2)
A0A4D6DKB1_9LAMI
336
0
37562
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKK9_9LAMI
335
0
37274
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKA5_9LAMI
335
0
37355
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKA6_9LAMI
327
0
36673
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKJ4_9LAMI
336
0
37444
TrEMBL
Secretory Pathway (Reliability: 5)
B9T9S0_RICCO
110
0
12725
TrEMBL
Secretory Pathway (Reliability: 5)
B9RVR5_RICCO
362
0
40257
TrEMBL
other Location (Reliability: 2)
B9S932_RICCO
359
0
40513
TrEMBL
other Location (Reliability: 3)
B9TKY3_RICCO
228
0
25633
TrEMBL
Secretory Pathway (Reliability: 2)
B9SGP1_RICCO
356
0
39539
TrEMBL
other Location (Reliability: 3)
B9RVR4_RICCO
372
0
41854
TrEMBL
other Location (Reliability: 2)
B9SGP4_RICCO
321
0
35518
TrEMBL
other Location (Reliability: 1)
A0A4D6DKU0_9LAMI
335
0
37274
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKF9_9LAMI
334
0
37766
TrEMBL
Secretory Pathway (Reliability: 5)
B9SGP2_RICCO
132
0
14574
TrEMBL
other Location (Reliability: 5)
A0A4D6DKK0_9LAMI
331
0
36999
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKD2_OCIBA
335
0
37551
TrEMBL
Secretory Pathway (Reliability: 5)
B9S931_RICCO
359
0
40392
TrEMBL
other Location (Reliability: 3)
A0A4D6DK91_9LAMI
332
0
37191
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DK86_9LAMI
335
0
37483
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKH4_9LAMI
327
0
36705
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKE5_9LAMI
333
0
37132
TrEMBL
Secretory Pathway (Reliability: 5)
B9RW38_RICCO
352
0
39194
TrEMBL
other Location (Reliability: 4)
B9RVQ9_RICCO
105
0
11912
TrEMBL
other Location (Reliability: 2)
A0A4D6DKH0_9LAMI
333
0
37342
TrEMBL
Secretory Pathway (Reliability: 5)
A0A396JW13_MEDTR
101
0
11465
TrEMBL
other Location (Reliability: 3)
A0A2P6QQ71_ROSCH
366
0
40157
TrEMBL
other Location (Reliability: 2)
A0A4D6DKB6_9LAMI
336
0
37673
TrEMBL
Secretory Pathway (Reliability: 5)
B9RVQ8_RICCO
356
0
39607
TrEMBL
other Location (Reliability: 5)
A0A4D6DKD9_9LAMI
315
0
34928
TrEMBL
other Location (Reliability: 5)
A0A396GKB8_MEDTR
144
0
15899
TrEMBL
other Location (Reliability: 5)
A0A4D6DKG7_9LAMI
336
0
37510
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKB7_9LAMI
335
0
37288
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKA0_9LAMI
335
0
37191
TrEMBL
Secretory Pathway (Reliability: 5)
B9RVR3_RICCO
362
0
40599
TrEMBL
other Location (Reliability: 2)
A0A2P6SIU6_ROSCH
362
0
39583
TrEMBL
other Location (Reliability: 1)
A0A4D6DKT6_OCIBA
335
0
37535
TrEMBL
Secretory Pathway (Reliability: 4)
B9SUX6_RICCO
345
0
38300
TrEMBL
other Location (Reliability: 2)
A0A4D6DKJ1_9LAMI
327
0
36549
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKG3_9LAMI
335
0
37426
TrEMBL
Secretory Pathway (Reliability: 5)
B9RVR6_RICCO
356
0
39851
TrEMBL
other Location (Reliability: 1)
A0A4D6DKU7_9LAMI
335
0
37260
TrEMBL
Secretory Pathway (Reliability: 5)
A0A4D6DKC7_9LAMI
327
0
36608
TrEMBL
Secretory Pathway (Reliability: 5)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
40000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purified recombinant MOMT5 and MOMT9 enzyme variants in complex with S-adenosyl-L-homocysteine (SAH), coniferyl alcohol, or sinapyl alcohol, hanging drop vapor diffusion method, crystallization from 22% (w/v) PEG 4000, 0.3 M Mg(NO3)2, pH 7.2, 1 mM DTT, 1 mM SAH, and 1 mM monolignols, X-ray diffraction structure determination and analysis at 1.60-1.73 A resolution, modeling
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
T133L/E165I/F175I/F166W/H169F
a promiscuous O-methyltransferase is incrementally evolved to constrain its substrate specificity to guaiacyl lignin precursors. The enzyme with nine amino acid substitutions is functionally specialized for selectively methylating the condensed lignin precursors. Specific remodeling the active site of a monolignol 4-O-methyltransferase creates an enzyme that specifically methylates the condensed guaiacyl lignin precursor coniferyl alcohol. The engineered promiscuous enzyme MOMT5 is built by remodelling of its substrate binding pocket by the addition of four substitutions, i.e. M26H, S30R, V33S, and T319M, yielding a mutant enzyme capable of discriminately etherifying the para-hydroxyl of coniferyl alcohol even in the presence of excess sinapyl alcohol. The engineered enzyme variant has a substantially reduced substrate binding pocket that imposes a clear steric hindrance thereby excluding bulkier lignin precursors
additional information
a number of monolignol 4-O-methyltransferase variants (MOMTs) are evolved that can trans-methylate the para-hydroxyls of monolignols, which prevents the incorporation of modified precursors into the lignin polymer by disrupting oxidative radical formation. The engineered enzyme is biochemically active against both coniferyl and sinapyl alcohol with similar catalytic turnover rates (e.g. MOMT3 and 4). Therefore, the transgenic plants with overexpressed MOMT maintained similar monomer composition and lignin structure as the wild-type plants
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme exhibits enhanced expression in juvenile stage that increases further during preflowering but decreases at flowering and further at postflowering
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Wang, J.; Pichersky, E.
Characterization of S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase involved in floral scent production in Clarkia breweri
Arch. Biochem. Biophys.
349
153-160
1998
Clarkia breweri (O04385), Clarkia breweri
brenda
Wang, J.; Dudareva, N.; Bhakta, S.; Raguso, R.A.; Pichersky, E.
Floral scent production in Clarkia breweri (Onagraceae). II. Localization and development modulation of the enzyme S-adenosyl-L-methionine:(iso)eugenol O-methyltransferase and phenylpropanoid emission
Plant Physiol.
114
213-221
1997
Clarkia breweri (O04385), Clarkia breweri
brenda
Gang, D.R.; Lavid, N.; Zubieta, C.; Chen, F.; Beuerle, T.; Lewinsohn, E.; Noel, J.P.; Pichersky, E.
Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family
Plant Cell
14
505-519
2002
Ocimum basilicum (Q93WU2), Ocimum basilicum
brenda
Wu, S.; Watanabe, N.; Mita, S.; Ueda, Y.; Shibuya, M.; Ebizuka, Y.
Two O-methyltransferases isolated from flower petals of Rosa chinensis var. spontanea involved in scent biosynthesis
J. Biosci. Bioeng.
96
119-128
2003
Rosa chinensis
brenda
Barkman, T.J.
Evidence for positive selection on the floral scent gene isoeugenol-O-methyltransferase
Mol. Biol. Evol.
20
168-172
2003
Clarkia breweri
brenda
Koeduka, T.; Baiga, T.J.; Noel, J.P.; Pichersky, E.
Biosynthesis of t-anethole in anise: characterization of t-anol/isoeugenol synthase and an O-methyltransferase specific for a C7-C8 propenyl side chain
Plant Physiol.
149
384-394
2009
Pimpinella anisum
brenda
Tarchoune, I.; Batour, O.; Harrathi, J.; Hamdaoui, G.; Lachal, M.; Ouerghi, Z.; Marzouk, B.
Effects of two sodium salts on fatty acid and essential oil composition of basil (Ocimum basilicum L.) leaves
Acta Physiol. Plant.
35
2365-2372
2013
Ocimum basilicum
-
brenda
Renu, I.K.; Haque, I.; Kumar, M.; Poddar, R.; Bandopadhyay, R.; Rai, A.; Mukhopadhyay, K.
Characterization and functional analysis of eugenol O-methyltransferase gene reveal metabolite shifts, chemotype specific differential expression and developmental regulation in Ocimum tenuiflorum L
Mol. Biol. Rep.
41
1857-1870
2014
Ocimum tenuiflorum (Q93WU2), Ocimum tenuiflorum
brenda
Cai, Y.; Bhuiya, M.; Shanklin, J.; Liu, C.
Engineering a monolignol 4-O-methyltransferase with high selectivity for the condensed lignin precursor coniferyl alcohol
J. Biol. Chem.
290
26715-26724
2015
Clarkia breweri (O04385)
brenda
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