Information on EC 2.5.1.80 - 7-dimethylallyltryptophan synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.5.1.80
-
RECOMMENDED NAME
GeneOntology No.
7-dimethylallyltryptophan synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alkenyl group transfer
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-
-
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:L-tryptophan 7-dimethylallyltransferase
This enzyme is more flexible towards the aromatic substrate than EC 2.5.1.34 (4-dimethylallyltryptophan synthase), but similar to that enzyme, accepts only dimethylallyl diphosphate as the prenyl donor.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + 1,6-dihydroxynaphthalene
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,6-diol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 1,7-dihydroxynaphthalene
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,7-diol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
35.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 1-naphthol
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalen-1-ol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 33.5% (FgaPT2 followed by 7-DMATS), 4.8% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-DL-7-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
-
19.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 2,6-dihydroxynaphthalene
diphosphate + 1-(3-methylbut-2-en-1-yl)naphthalene-2,6-diol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 2,7-dihydroxynaphthalene
diphosphate + 1-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol + 3-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol + 7-[(3-methylbut-2-en-1-yl)oxy]naphthalen-2-ol + 1,6-bis(3-methylbut-2-en-1-yl)naphthalene-2,7-diol
show the reaction diagram
-
-
1-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol is the major product
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
89.4% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-bromo-DL-tryptophan
diphosphate + 5-bromo-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
7.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-fluoro-L-tryptophan
diphosphate + 5-fluoro-7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
10.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
26.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 10.3% (FgaPT2 followed by 7-DMATS), 3.5% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 5-methoxy-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
13.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 24.3% (FgaPT2 followed by 7-DMATS), 0.9% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
74.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
33.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 2.6% (FgaPT2 followed by 7-DMATS), 1.5% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
19.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-DL-tryptophan + ?
show the reaction diagram
-
0.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + apigenin
diphosphate + ?
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + biochanin A
diphosphate + gancaonin A
show the reaction diagram
-
15.9% activity compared to substrate L-tryptophan
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-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + cyclo-L-7-(3-methylbut-2-enyl)-Trp-Gly
show the reaction diagram
-
1.8% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + D-tryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 4.3% (FgaPT2 followed by 7-DMATS), 2.6% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-7-(3-methylbut-2-enyl)-tryptophan
show the reaction diagram
dimethylallyl diphosphate + DL-indole-3-lactic acid
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 35.7% (FgaPT2 followed by 7-DMATS), 16.7% (7-DMATS followed by FgaPT2)
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-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 7-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
show the reaction diagram
-
4.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + eriodictyol
diphosphate + 6-(3-methylbut-2-enyl)eriodictyol
show the reaction diagram
-
19.0% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + genistein
diphosphate + wighteone
show the reaction diagram
-
10.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + hesperetin
diphosphate + sigmoidin B
show the reaction diagram
-
1.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + indole-3-acetic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-acetic acid
show the reaction diagram
-
10.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-butyric acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-butyric acid
show the reaction diagram
-
9.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-propionic acid
show the reaction diagram
-
8.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-pyruvic acid
show the reaction diagram
-
4.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-abrine
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 92.7% (FgaPT2 followed by 7-DMATS), 11.3% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 31.5% (FgaPT2 followed by 7-DMATS), 6.6% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-beta-homotryptophan
show the reaction diagram
-
28.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-Trp-Gly
diphosphate + L-7-(3-methylbut-2-enyl)-Trp-Gly
show the reaction diagram
-
10.9% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 89.7% (FgaPT2 followed by 7-DMATS), 20% (7-DMATS followed by FgaPT2)
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-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-7-(3-methylbut-2-enyl)-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + L-7-(gamma,gamma-dimethylallyl)tryptophan hydroxamate
show the reaction diagram
-
4.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
show the reaction diagram
-
7.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + luteolin
diphosphate + ?
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-DL-7-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
-
7.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-7-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
i.e. L-abrine
82.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + naringenin
diphosphate + 6-(3-methylbut-2-enyl)naringenin
show the reaction diagram
-
1.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + phloretin
diphosphate + 6-dimethylallyl-5,7,9,1'-tetrahydroxydihydrochalcone
show the reaction diagram
-
17.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + tryptamine
?
show the reaction diagram
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 11% (FgaPT2 followed by 7-DMATS), 6.3% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + tryptamine
diphosphate + 7-(3-methylbut-2-enyl)-tryptamine
show the reaction diagram
-
7.5% of the yield with L-tryptophan
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
required
additional information
addition of divalent cations is not required
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
phloretin
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shows substrate inhibition at 1 mM or higher concentrations
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.07
Biochanin A
-
pH not specified in the publication, 37C
0.067
dimethylallyl diphosphate
pH 7.5, 37C
1.26
eriodictyol
-
pH not specified in the publication, 37C
0.16
genistein
-
pH not specified in the publication, 37C
1.1
hesperetin
-
pH not specified in the publication, 37C
0.137 - 0.14
L-tryptophan
0.99
naringenin
-
pH not specified in the publication, 37C
0.13
phloretin
-
pH not specified in the publication, 37C
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.019
Biochanin A
Aspergillus fumigatus
-
pH not specified in the publication, 37C
0.39
eriodictyol
Aspergillus fumigatus
-
pH not specified in the publication, 37C
0.027
genistein
Aspergillus fumigatus
-
pH not specified in the publication, 37C
0.026
hesperetin
Aspergillus fumigatus
-
pH not specified in the publication, 37C
0.23
L-tryptophan
Aspergillus fumigatus
-
pH and temperature not specified in the publication
0.023
naringenin
Aspergillus fumigatus
-
pH not specified in the publication, 37C
0.036
phloretin
Aspergillus fumigatus
-
pH not specified in the publication, 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.261
Biochanin A
Aspergillus fumigatus
-
pH not specified in the publication, 37C
1435
0.312
eriodictyol
Aspergillus fumigatus
-
pH not specified in the publication, 37C
2485
0.171
genistein
Aspergillus fumigatus
-
pH not specified in the publication, 37C
377
0.024
hesperetin
Aspergillus fumigatus
-
pH not specified in the publication, 37C
2081
1.643
L-tryptophan
Aspergillus fumigatus
-
pH and temperature not specified in the publication
119
0.023
naringenin
Aspergillus fumigatus
-
pH not specified in the publication, 37C
586
0.286
phloretin
Aspergillus fumigatus
-
pH not specified in the publication, 37C
1762
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 37
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 53000, calculated
monomer
1 * 50000, SDS-PAGE, 1 * 54000, calculated, His-tagged recombinant protein
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
37C, absence of substrate, 16 h, 80% residual activity
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged 7-DMATS from Escherichia coli strains XL1 Blue or M15 or from Saccharomyces cerevisiae strain INVSc1 by nickel affinity chromatography
recombinant protein
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
7-DMATS expression in Escherichia coli
-
expressed as a recombinant protein
-
expression in Escherichia coli, His-tagged protein
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expression of His-tagged 7-DMATS in Escherichia coli strains XL1 Blue or M15 or in Saccharomyces cerevisiae strain INVSc1
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
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the combination of the two dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) can be successfully used for chemoenzymatic synthesis of the diprenylated derivatives. The potential of recombinant enzymes from secondary metabolite biosynthesis as promising tools for the production of designed compounds is demonstrated
drug development
synthesis