Information on EC 2.5.1.B31 - 5-dimethylallyltryptophan synthase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.5.1.B31
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
5-dimethylallyltryptophan synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:L-tryptophan 5-dimethylallyltransferase
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
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
2-pentenyl diphosphate + L-tryptophan
diphosphate + 6-(2-trans-pentenyl)-L-tryptophan
show the reaction diagram
-
91% of the activity with dimethylallyl diphosphate
-
-
?
dimethylallyl diphosphate + 1-methyl-DL-tryptophan
diphosphate + 1-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-5-(3-methylbut-2-en-1-yl)tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactate
diphosphate + 2-hydroxy-3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + indole-3-propionate
diphosphate + 3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-abrine
diphosphate + N-methyl-5-(3-methylbut-2-en-1-yl)-L-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + (3S)-3-amino-4-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]butanoic acid
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-5-(3-methylbut-2-en-1-yl)tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + trans-indole-3-acrylate
diphosphate + (2E)-3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]prop-2-enoic acid
show the reaction diagram
-
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(2-trans-butenyl)-L-tryptophan + 6-(2-trans-butenyl)-L-tryptophan
show the reaction diagram
-
22% of the activity with dimethylallyl diphosphate
-
-
?
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 + 5-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
activates 2fold
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
1-methyl-DL-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.131
2-pentenyl diphosphate
-
37C, pH not specified in the publication
0.25
4-methyl-DL-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.27
6-fluoro-DL-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
1
6-methyl-DL-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.47
7-methyl-DL-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.076
dimethylallyl diphosphate
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.67
DL-indole-3-lactate
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.39
indole-3-propionate
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.26
L-abrine
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.97
L-beta-homotryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.034
L-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.04
methylallyl diphosphate
-
37C, pH not specified in the publication
0.35
N-acetyl-DL-tryptophan
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.4
trans-indole-3-acrylate
pH 7.5, 37C, recombinant His-tagged 5-DMATS
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.059
1-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.023
2-pentenyl diphosphate
Aspergillus clavatus
-
37C, pH not specified in the publication
0.29
4-methyl-DL-tryptophan
0.76
6-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.4
7-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
1.3
dimethylallyl diphosphate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.43
DL-indole-3-lactate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.39
indole-3-propionate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.4
L-abrine
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.15
L-beta-homotryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.87
L-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.005
methylallyl diphosphate
Aspergillus clavatus
-
37C, pH not specified in the publication
0.1
N-acetyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
0.14
trans-indole-3-acrylate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.59
1-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
5382
0.174
2-pentenyl diphosphate
Aspergillus clavatus
-
37C, pH not specified in the publication
15354
1.16
4-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
11621
1.074
6-fluoro-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
4677
0.76
6-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
4145
0.851
7-methyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
6249
1.538
dimethylallyl diphosphate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
157
0.642
DL-indole-3-lactate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
42434
1
indole-3-propionate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
13185
1.538
L-abrine
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
27257
0.155
L-beta-homotryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
7715
25.59
L-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
119
0.136
methylallyl diphosphate
Aspergillus clavatus
-
37C, pH not specified in the publication
15353
0.286
N-acetyl-DL-tryptophan
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
9226
0.35
trans-indole-3-acrylate
Aspergillus clavatus
A1CRX0
pH 7.5, 37C, recombinant His-tagged 5-DMATS
42435
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 37
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged 5-DMATS from Escherichia coli strain BL21 or Saccharomyces cerevisiae strain INVSc1 by nickel affinity chromatography
recombinant solube His-tagged 5-DMATS from Escherichia coli strain M15 by nickel affinity chromatography to near homogeneity
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5-DMATS, DNA and amino acid sequence determination and analysis, expression in Escherichia coli strains BL21, XL1 Blue, or M15 or in Saccharomyces cerevisiae strain INVSc1
gene ACLA_031240 or 5-dmats, DNA and amino acid sequence determination and analysis, expression as solube His-tagged protein in Escherichia coli strain M15, subcloning in Escherichia coli strain XL1 Blue
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
additional information
-
prenyltransferases of the dimethylallyl-tryptophan synthase superfamily catalyze Friedel-Crafts alkylation with high flexibility for aromatic substrates, but the high specificity for dimethylallyl diphosphate prohibits their application as biocatalysts