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Information on EC 2.3.1.196 - benzyl alcohol O-benzoyltransferase for references in articles please use BRENDA:EC2.3.1.196Word Map on EC 2.3.1.196
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The enzyme appears in viruses and cellular organisms
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benzyl alcohol O-benzoyltransferase
-
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benzoyl-CoA + benzyl alcohol = CoA + benzyl benzoate
-
-
-
-
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benzoate biosynthesis I (CoA-dependent, beta-oxidative)
-
-
salicortin biosynthesis
-
-
volatile benzenoid biosynthesis I (ester formation)
-
-
volatile esters biosynthesis (during fruit ripening)
-
-
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benzoyl-CoA:benzyl alcohol O-benzoyltransferase
The enzyme is involved in volatile benzenoid and benzoic acid biosynthesis. The enzyme from Petunia hybrida also catalyses the formation of 2-phenylethyl benzoate from benzoyl-CoA and 2-phenylethanol. The apparent catalytic efficiency of the enzyme from Petunia hybrida with benzoyl-CoA is almost 6-fold higher than with acetyl-CoA [1].
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benzoyl CoA:benzyl alcohol/phenylethanol benzoyltransferase
-
-
benzoyl-CoA: salicyl alcohol O-benzoyltransferase
B9I6S9
-
benzoyl-CoA:benzyl alcohol benzoyl transferase
-
benzoyl-CoA:benzyl alcohol/phenylethanol benzoyltransferase
-
benzoyl-coenzyme A:benzyl alcohol benzoyl transferase
-
BEBT
-
BPBT
-
-
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-
UniProt
brenda
-
UniProt
brenda
-
UniProt
brenda
-
SwissProt
brenda
cv Mitchell
UniProt
brenda
cv. Mitchell
-
-
brenda
cv. Mitchell ‘Diploid’
-
-
brenda
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malfunction
-
generation of transgenic petunia plants in which the expression of BPBT, the gene encoding the enzyme that uses benzoyl-CoA and benzyl alcohol to make benzyl benzoate, is reduced or eliminated. Elimination of benzyl benzoate formation decreases the endogenous pool of benzoic acid and methyl benzoate emission but increases emission of benzyl alcohol and benzaldehyde, confirming the contribution of benzyl benzoate to benzoic acid formation. Suppression of BPBT activity also affects the overall morphology of petunia plants, resulting in larger flowers and leaves, thicker stems, and longer internodes, which is consistent with the increased auxin transport in transgenic plants
physiological function
-
it is hypothesized that PhBPBT and subsequent benzyl benzoate production is involved in defencerelated processes in the corolla prior to pollination in the ovary immediately following fertilization, and in vegetative tissue in response to wounding
physiological function
the enzyme catalyzes the formation of benzyl benzoate, a minor constituent of the Clarkia breweri floral aroma
physiological function
the enzyme involved in benzenoid metabolism
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acetyl-CoA + 3-hydroxybenzyl alcohol
3-hydroxybenzyl acetate + CoA
41% of the activity with benzoyl-CoA
-
-
?
acetyl-CoA + benzyl alcohol
acetyl benzoate + CoA
turnover number for acetyl is 5-8% of that with benzoyl-CoA
-
-
?
acetyl-CoA + benzyl alcohol
benzyl acetate + CoA
acetyl-CoA + salicyl alcohol
salicyl acetate + CoA
43.5% of the activity with benzoyl-CoA
-
-
?
benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
benzoyl-CoA + 3-hydroxybenzyl alcohol
3-hydroxybenzyl benzoate + CoA
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
benzoyl-CoA + benzyl alcohol
CoA + benzyl benzoate
-
-
-
?
benzoyl-CoA + cinnamyl alcohol
cinnamyl benzoate + CoA
benzoyl-CoA + coniferyl alcohol
coniferyl benzoate + CoA
71% of the activity with salicyl alcohol
-
-
?
benzoyl-CoA + salicyl alcohol
salicyl benzoate + CoA
-
-
-
?
cinnamoyl-CoA + 3-benzyl alcohol
benzyl cinnamate + CoA
28.6% of the activity with benzoyl-CoA
-
-
?
cinnamoyl-CoA + benzyl alcohol
? + CoA
the Km-value for cinnamoyl-CoA (0.464 mM) strongly suggests that acetyl-CoA is not commonly used by BEBT as the acyl donor in vivo
-
-
?
cinnamoyl-CoA + salicyl alcohol
salicyl cinnamoate + CoA
11.5% of the activity with benzoyl-CoA
-
-
?
additional information
?
-
acetyl-CoA + benzyl alcohol
benzyl acetate + CoA
the Km-value for acetyl-CoA (0.818 mM) strongly suggests that acetyl-CoA is not commonly used by BEBT as the acyl donor in vivo
-
-
?
acetyl-CoA + benzyl alcohol
benzyl acetate + CoA
13% of the activity with benzoyl-CoA
-
-
?
acetyl-CoA + benzyl alcohol
benzyl acetate + CoA
51% of the activity with benzoyl-CoA
-
-
?
benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
-
-
-
?
benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
-
PhBPBT is responsible for the biosynthesis of both benzyl benzoate and 2-phenylethyl benzoate from benzyl alcohol and phenylethanol, respectively
-
-
?
benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
the enzyme is most likely responsible for the formation of both 2-phenylethyl benzoate and benzyl benzoate in vivo
-
-
?
benzoyl-CoA + 3-hydroxybenzyl alcohol
3-hydroxybenzyl benzoate + CoA
112% of the activity with benzyl alcohol
-
-
?
benzoyl-CoA + 3-hydroxybenzyl alcohol
3-hydroxybenzyl benzoate + CoA
97% of the activity with salicyl alcohol
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
the enzyme catalyzes the formation of benzyl benzoate, a minor constituent of the Clarkia breweri floral aroma
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
-
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
PhBPBT is responsible for the biosynthesis of both benzyl benzoate and 2-phenylethyl benzoate from benzyl alcohol and phenylethanol, respectively
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
the enzyme is most likely responsible for the formation of both 2-phenylethyl benzoate and benzyl benzoate in vivo
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
-
-
?
benzoyl-CoA + cinnamyl alcohol
cinnamyl benzoate + CoA
-
-
-
?
benzoyl-CoA + cinnamyl alcohol
cinnamyl benzoate + CoA
44% of the activity with salicyl alcohol
-
-
?
additional information
?
-
coumaroyl-CoA does not act as substrate
-
-
-
additional information
?
-
no activity with acetyl-CoA at concentrations below 1 mM
-
-
-
additional information
?
-
no substrates: cinnamoyl-CoA, coumaroyl-CoA, or caffeoyl-CoA
-
-
-
additional information
?
-
B9I6S9
no substrates: cinnamoyl-CoA, coumaroyl-CoA, or caffeoyl-CoA
-
-
-
additional information
?
-
-
no substrates: cinnamoyl-CoA, coumaroyl-CoA, or caffeoyl-CoA
-
-
-
additional information
?
-
no substrates: coumaroyl-CoA, or caffeoyl-CoA
-
-
-
additional information
?
-
B9I6S9
no substrates: coumaroyl-CoA, or caffeoyl-CoA
-
-
-
additional information
?
-
-
no substrates: coumaroyl-CoA, or caffeoyl-CoA
-
-
-
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benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
-
PhBPBT is responsible for the biosynthesis of both benzyl benzoate and 2-phenylethyl benzoate from benzyl alcohol and phenylethanol, respectively
-
-
?
benzoyl-CoA + 2-phenylethanol
2-phenylethyl benzoate + CoA
Q6E593
the enzyme is most likely responsible for the formation of both 2-phenylethyl benzoate and benzyl benzoate in vivo
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
Q8GT21
the enzyme catalyzes the formation of benzyl benzoate, a minor constituent of the Clarkia breweri floral aroma
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
-
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
-
PhBPBT is responsible for the biosynthesis of both benzyl benzoate and 2-phenylethyl benzoate from benzyl alcohol and phenylethanol, respectively
-
-
?
benzoyl-CoA + benzyl alcohol
benzyl benzoate + CoA
Q6E593
the enzyme is most likely responsible for the formation of both 2-phenylethyl benzoate and benzyl benzoate in vivo
-
-
?
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Ca2+
the monovalent and divalent cations K+, Ca2+, Mg2+ and Mn2+ can increase enzyme activity by 50–70% at 5 mM
K+
the monovalent and divalent cations K+, Ca2+, Mg2+ and Mn2+ can increase enzyme activity by 50–70% at 5 mM
Mg2+
the monovalent and divalent cations K+, Ca2+, Mg2+ and Mn2+ can increase enzyme activity by 50–70% at 5 mM
Mn2+
the monovalent and divalent cations K+, Ca2+, Mg2+ and Mn2+ can increase enzyme activity by 50–70% at 5 mM
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Ca2+
5 mM, strong inhibition
Co2+
5 mM, strong inhibition
Mg2+
5 mM, strong inhibition
Cu2+
5 mM, strong inhibition
Zn2+
5 mM, strong inhibition
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0.686
2-phenylethanol
pH 7.7, 22°C, cosubstrate: 2-phenylethanol
0.057 - 0.067
3-Hydroxybenzyl alcohol
0.00842 - 1.56
benzoyl-CoA
0.019 - 0.444
benzyl alcohol
0.464
cinnamoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
0.0978
cinnamyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
0.044 - 0.339
salicyl alcohol
0.057
3-Hydroxybenzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
0.067
3-Hydroxybenzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
0.246
acetyl-CoA
cosubstrate salicyl alcohol, pH 7.0, 30°C
0.365
acetyl-CoA
cosubstrate benzyl alcohol, pH 7.0, 30°C
0.682
acetyl-CoA
pH 7.7, 22°C, cosubstrate: benzyl alcohol
0.818
acetyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
0.00842
benzoyl-CoA
pH 7.5, 20-22°C, cosubstrate: benzyl alcohol, recombinant enzyme
0.0118
benzoyl-CoA
pH 7.5, 20-22°C, cosubstrate: benzyl alcohol, native enzyme
0.0205
benzoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
0.035
benzoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
0.046
benzoyl-CoA
cosubstrate salicyl alcohol, pH 7.0, 30°C
0.052
benzoyl-CoA
cosubstrate benzyl alcohol, pH 7.0, 30°C
0.063
benzoyl-CoA
cosubstrate 3-hydroxybenzyl alcohol, pH 7.0, 30°C; cosubstrate 3-hydroxybenzyl alcohol, pH 7.0, 30°C
0.875
benzoyl-CoA
pH 7.7, 22°C, cosubstrate: 2-phenylethanol
1.56
benzoyl-CoA
pH 7.7, 22°C, cosubstrate: benzyl alcohol
0.019
benzyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
0.029
benzyl alcohol
pH 7.7, 22°C, cosubstrate: acetyl-CoA
0.0468
benzyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
0.059
benzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
0.395
benzyl alcohol
cosubstrate acetyl-CoA, pH 7.0, 30°C
0.444
benzyl alcohol
pH 7.7, 22°C, cosubstrate: benzyl alcohol
0.044
salicyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
0.339
salicyl alcohol
cosubstrate acetyl-CoA, pH 7.0, 30°C
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35.8
2-phenylethanol
pH 7.7, 22°C, cosubstrate: 2-phenylethanol
1.42 - 1.97
3-Hydroxybenzyl alcohol
0.4 - 85.2
benzyl alcohol
0.9
cinnamoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
47.2
cinnamyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
0.35 - 2.06
salicyl alcohol
1.42
3-Hydroxybenzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
1.97
3-Hydroxybenzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
0.32
acetyl-CoA
cosubstrate benzyl alcohol, pH 7.0, 30°C
0.43
acetyl-CoA
cosubstrate salicyl alcohol, pH 7.0, 30°C
4.4
acetyl-CoA
pH 7.7, 22°C, cosubstrate: benzyl alcohol
21.5
acetyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
0.045
benzoyl-CoA
pH 7.5, 20-22°C, cosubstrate: benzyl alcohol, native enzyme; pH 7.5, 20-22°C, cosubstrate: benzyl alcohol, recombinant enzyme
1.72
benzoyl-CoA
cosubstrate benzyl alcohol, pH 7.0, 30°C
2.01
benzoyl-CoA
cosubstrate 3-hydroxybenzyl alcohol, pH 7.0, 30°C
2.06
benzoyl-CoA
cosubstrate salicyl alcohol, pH 7.0, 30°C
2.25
benzoyl-CoA
cosubstrate 3-hydroxybenzyl alcohol, pH 7.0, 30°C
57.1
benzoyl-CoA
pH 7.7, 22°C, cosubstrate: benzyl alcohol
81.3
benzoyl-CoA
pH 7.7, 22°C, cosubstrate: 2-phenylethanol
124
benzoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
0.4
benzyl alcohol
cosubstrate acetyl-CoA, pH 7.0, 30°C
1.61
benzyl alcohol
pH 7.7, 22°C, cosubstrate: acetyl-CoA
1.79
benzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
36.9
benzyl alcohol
pH 7.7, 22°C, cosubstrate: benzyl alcohol
85.2
benzyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
0.35
salicyl alcohol
cosubstrate acetyl-CoA, pH 7.0, 30°C
2.06
salicyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
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52.8
2-phenylethanol
pH 7.7, 22°C, cosubstrate: 2-phenylethanol
30.4 - 32.6
3-Hydroxybenzyl alcohol
0.4
cinnamoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
4.6
cinnamyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
30.4
3-Hydroxybenzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
32.6
3-Hydroxybenzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
0.9
acetyl-CoA
cosubstrate benzyl alcohol, pH 7.0, 30°C
1.7
acetyl-CoA
cosubstrate salicyl alcohol, pH 7.0, 30°C
6.68
acetyl-CoA
pH 7.7, 22°C, cosubstrate: benzyl alcohol
17.5
acetyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
2.5
benzoyl-CoA
pH 7.7, 22°C, cosustrate: benzyl alcohol
2.85
benzoyl-CoA
pH 7.5, 20-22°C, cosubstrate: benzyl alcohol, recombinant enzyme
3.81
benzoyl-CoA
pH 7.5, 20-22°C, cosubstrate: benzyl alcohol, native enzyme
32.1
benzoyl-CoA
cosubstrate 3-hydroxybenzyl alcohol, pH 7.0, 30°C
33.2
benzoyl-CoA
cosubstrate benzyl alcohol, pH 7.0, 30°C
35.5
benzoyl-CoA
cosubstrate 3-hydroxybenzyl alcohol, pH 7.0, 30°C
37.2
benzoyl-CoA
pH 7.7, 22°C, cosubstrate: benzyl alcohol
45
benzoyl-CoA
cosubstrate salicyl alcohol, pH 7.0, 30°C
92.2
benzoyl-CoA
pH 7.7, 22°C, cosubstrate: 2-phenylethanol
1
benzyl alcohol
cosubstrate acetyl-CoA, pH 7.0, 30°C
4
benzyl alcohol
pH 7.7, 22°C, cosustrate: benzoyl-CoA
30.4
benzyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
56.8
benzyl alcohol
pH 7.7, 22°C, cosubstrate: acetyl-CoA
83.1
benzyl alcohol
pH 7.7, 22°C, cosubstrate: benzyl alcohol
1
salicyl alcohol
cosubstrate acetyl-CoA, pH 7.0, 30°C
46.6
salicyl alcohol
cosubstrate benzoyl-CoA, pH 7.0, 30°C
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7.7
-
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5.5 - 8.5
at least 50% of maximum activity; at least 50% of maximum activity
6.5 - 9
pH 6.5: 39% of maximal activity, pH 9.0: 69% of maximal activity
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22
assay at
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6.12
calculated from sequence
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the majority of the enzyme in grape tissues is localized to the outer fruit mesocarp
brenda
BPBT mRNA transcripts predominante in the limb of petunia corollas, the parts of the flower that are primarily responsible for scent production and emission in petunia. The steady-state BPBT mRNA level in corolla limbs is developmentally regulated, peaking 1 to 2 d after anthesis and changing rhythmically during a daily light/dark cycle closely correlating with the pattern of BPBT activity and benzylbenzoate accumulation
brenda
the majority of the enzyme in grape tissues is localized to the outer fruit mesocarp
brenda
30% of the activity in stigma
brenda
30% of the activity in stigma
brenda
30% of the activity in stigma
brenda
the BEBT gene is expressed in different parts of the flowers with maximal RNA transcript levels in the stigma
brenda
the BEBT gene is expressed in different parts of the flowers with maximal RNA transcript levels in the stigma
brenda
-
-
brenda
no expression in the leaves under normal conditions. BEBT expression is induced in damaged leaves, reaching a maximum 6 h after damage occurres
brenda
induced upon wounding
brenda
-
brenda
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47000 - 49500
gel filtration
50000
x * 50000, SDS-PAGE
50650
calculated from sequence
51010
calculated from sequence
51014
x * 51014, calculated from sequence
51040
calculated from sequence
51900
x * 51900, calculated and SDS-PAGE
52600
x * 52600, calculated and SDS-PAGE
55000
1 * 55000, SDS-PAGE
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monomer
1 * 50650, calculated from sequence; 1 * 55000, SDS-PAGE
?
x * 51014, calculated from sequence
?
x * 51900, calculated and SDS-PAGE; x * 52600, calculated and SDS-PAGE
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37
30 min, 20% loss of activity
45
5 min, 80% loss of activity
50
30 min, complete inactivation
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complete, non-fusion BEBT enzyme from the crude Escherichia coli extract
-
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expression in Escherichia coli
expression in Escherichia coli; expression in Escherichia coli
expression in Escherichia coli
expression in Escherichia coli
expression in Escherichia coli
expression in Escherichia coli
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PhBPBT is regulated by both light and an endogenous circadian rhythm, while it is also differentially regulated in response to ethylene in a tissue-specific manner. 24 hours following pollination of flowers, expression of PhBPBT decreases in the corolla, while it increases in the ovary after 48 h. This is caused by ethylene that is emitted from the flower coinciding with fertilization as this is not observed in transgenic ethylene-insensitive plants (CaMV35S::etr1-1, 44568). Ethylene is also emitted from vegetative tissue of petunia following mechanical wounding, resulting in an increase in PhBPBT expression in the leaves where expression is normally below detection levels
-
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H166A
HTMSD motif altered to ATMSD. 97% loss of activity
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ACMAT_VITLA
449
50182
Swiss-Prot
BEBT_CLABR
456
50650
Swiss-Prot
BEBT_TOBAC
460
51014
Swiss-Prot
A0A2P6PB83_ROSCH
526
58487
TrEMBL
A0A2G9HPK0_9LAMI
176
19873
TrEMBL
A0A2P6PB66_ROSCH
462
51403
TrEMBL
A0A2P6PB74_ROSCH
435
48497
TrEMBL
A0A2G9HPC7_9LAMI
181
20498
TrEMBL
A0A2P6PB85_ROSCH
462
51146
TrEMBL
A0A2P6PB55_ROSCH
462
51420
TrEMBL
A0A2P6PRD1_ROSCH
463
51070
TrEMBL
Q6E593_PETHY
460
51042
TrEMBL
A0A0B4VSM7_POPTR
460
50912
TrEMBL
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Dexter, R.J.; Verdonk, J.C.; Underwood, B.A.; Shibuya, K.; Schmelz, E.A.; Clark, D.G.
Tissue-specific PhBPBT expression is differentially regulated in response to endogenous ethylene
J. Exp. Bot.
59
609-618
2008
Petunia x hybrida
brenda
Orlova, I.; Marshall-Colon, A.; Schnepp, J.; Wood, B.; Varbanova, M.; Fridman, E.; Blakeslee, J.J.; Peer, W.A., Murphy, A.S.; Rhodes, D.; Pichersky, E.; Dudareva, N.
Reduction of benzenoid synthesis in petunia flowers reveals multiple pathways to benzoic acid and enhancement in auxin transport
Plant Cell
18
3458-3475
2006
Petunia x hybrida
brenda
D'Auria, J.C.; Chen, F.; Pichersky, E.
Characterization of an acyltransferase capable of synthesizing benzyl benzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri
Plant Physiol.
130
466-476
2002
Clarkia breweri (Q8GT21), Nicotiana tabacum (Q8GT20)
brenda
Boatright, J.; Negre, F.; Chen, X.; Kish, C.M.; Wood, B.; Peel, G.; Orlova, I.; Gang, D.; Rhodes, D.; Dudareva, N.
Understanding in vivo benzenoid metabolism in petunia petal tissue
Plant Physiol.
135
1993-2011
2004
Petunia x hybrida (Q6E593)
brenda
Wang, J.; De Luca, V.
The biosynthesis and regulation of biosynthesis of Concord grape fruit esters, including ’foxy’ methylanthranilate
Plant J.
44
606-619
2005
Vitis labrusca (Q3ZPN4)
brenda
Chedgy, R.J.; Koellner, T.G.; Constabel, C.P.
Functional characterization of two acyltransferases from Populus trichocarpa capable of synthesizing benzyl benzoate and salicyl benzoate, potential intermediates in salicinoid phenolic glycoside biosynthesis
Phytochemistry
113
149-159
2015
Populus trichocarpa (A0A0B4VSM7), Populus trichocarpa (B9I6S9), Populus trichocarpa
brenda
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