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Information on EC 2.5.1.B31 - 5-dimethylallyltryptophan synthase
for references in articles please use BRENDA:EC2.5.1.B31preliminary BRENDA-supplied EC number
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EC Tree
2.5.1.B31 5-dimethylallyltryptophan synthaseSpecify your search results
Word Map
- 2.5.1.B31
- indole
- synthesis
- 7-dmats
- fgapt2
-
dmapp
-
actinomycete
-
chemoenzymatic
-
regioselectivity
- coelicolor
- dimethylallyltryptophans
-
regiospecific
-
geranyl
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
5-dmats, 5-dmatssc, sco7467, 5-dimethylallyltryptophan synthase, eaw08391, tryptophan c5-prenyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
5-DMATS
5-DMATSSc
SCO7467
tryptophan C5-prenyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
5-dimethylallyltryptophan synthase performs the highly regiospecific regular prenylation at C-5 of the indole nucleus of the simple indole derivatives
dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Friedel-Crafts alkylation
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:L-tryptophan 5-dimethylallyltransferase
-
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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
2-pentenyl diphosphate + L-tryptophan
diphosphate + 6-(2-trans-pentenyl)-L-tryptophan
-
91% of the activity with dimethylallyl diphosphate
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 5-benzyl-L-tryptophan
-
C-5 prenylation
-
-
?
dimethylallyl diphosphate + 1-methyl-DL-tryptophan
diphosphate + 1-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
-
-
?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-5-(3-methylbut-2-enyl)-L-tryptophan
-
46.9% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
-
-
?
dimethylallyl diphosphate + 4-methyl-L-tryptophan
diphosphate + 4-methyl-5-(3-methylbut-2-enyl)-L-tryptophan
-
56.6% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-5-(3-methylbut-2-en-1-yl)tryptophan
-
-
-
?
dimethylallyl diphosphate + 6-fluoro-L-tryptophan
diphosphate + 6-fluoro-5-(3-methylbut-2-enyl)-L-tryptophan
-
69.5% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
-
-
?
dimethylallyl diphosphate + 6-methyl-L-tryptophan
diphosphate + 6-methyl-5-(3-methylbut-2-enyl)-L-tryptophan
-
53.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 6-[(2E)-pent-2-en-1-yl]-L-tryptophan
diphosphate + 7-[(2E)-pent-2-en-1-yl]-L-tryptophan + 5-[(2E)-pent-2-en-1-yl]-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-5-(3-methylbut-2-en-1-yl)-tryptophan
-
-
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-5-(3-methylbut-2-enyl)-DL-tryptophan
-
57.8% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (1S,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-1-[[5,6-bis(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-4-methyl-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + beta-homo-L-tryptophan
?
-
48.8% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
diphosphate + (1R,4R)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
diphosphate + (1R,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
diphosphate + (1S,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
diphosphate + (1S,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactate
diphosphate + 2-hydroxy-3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
?
-
67.3% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
diphosphate + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
diphosphate + (1R,4S)-4-methyl-1-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4S)-1-[[5,6-bis(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-4-methyl-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
-
-
-
-
?
dimethylallyl diphosphate + indole-3-propionate
diphosphate + 3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]propanoic acid
-
-
-
?
dimethylallyl diphosphate + indole-3-propionic acid
?
-
70.7% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + L-abrine
?
-
90.9% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + L-abrine
diphosphate + N-methyl-5-(3-methylbut-2-en-1-yl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + (3S)-3-amino-4-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]butanoic acid
-
-
-
?
dimethylallyl diphosphate + L-o-Tyr
diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine
-
C-3 prenylation
3-dimethylallyl-L-tyrosine
-
?
dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine
-
C-5 prenylation, proposed reaction mechanism, overview. Low activity
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-5-(3-methylbut-2-en-1-yl)tryptophan
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-5-(3-methylbut-2-enyl)-DL-tryptophan
-
54.4% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + trans-indole-3-acrylate
diphosphate + (2E)-3-[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]prop-2-enoic acid
-
-
-
?
dimethylallyl diphosphate + trans-indole-3-acrylic acid
?
-
38.0% of the activity with L-Trp
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(2-trans-butenyl)-L-tryptophan + 6-(2-trans-butenyl)-L-tryptophan
-
22% of the activity with dimethylallyl diphosphate
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 5-(pent-2-enyl)-L-tryptophan
-
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 5-(pent-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 5-(pent-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 6-(pent-2-enyl)-L-tryptophan
-
C-6 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 6-(pent-2-enyl)-L-tryptophan
-
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 6-(pent-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 6-(pent-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 7-(pent-2-enyl)-L-tryptophan
-
C-5, C-6 and C-7 prenylation
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 7-(pent-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 6-benzyl-L-tryptophan
-
C-6 prenylation
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 6-benzyl-L-tryptophan
-
C-6 prenylation
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 6-benzyl-L-tryptophan
C-6 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
product analysis by mass spectrometry and NMR
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
best substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
C-5 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
the product is further processed to 5-dimethylallylindole-3-acetonitrile
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
product identification by NMR and mass spectroscopy
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
best substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
best substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
best substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
product identification by NMR and mass spectroscopy
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
-
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
-
-
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(but-2-enyl)-L-tryptophan
-
C-5 and C-6 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(but-2-enyl)-L-tryptophan
-
C-5, C-6 and C-7 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(but-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 6-(but-2-enyl)-L-tryptophan
-
C-5 and C-6 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 6-(but-2-enyl)-L-tryptophan
-
C-5, C-6 and C-7 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 6-(but-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 7-(but-2-enyl)-L-tryptophan
-
C-5, C-6 and C-7 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 7-(but-2-enyl)-L-tryptophan
C-5, C-6 and C-7 prenylation
-
-
?
additional information
?
-
in presence of dimethylallyl diphosphate, the recombinant enzyme accepts simple indole derivatives with L-tryptophan as the best substrate, it is also active with tryptophan-containing cyclic dipeptides but with much lower conversion yields. No activity with geranyl or farnesyl diphosphate
-
-
?
additional information
?
-
-
in presence of dimethylallyl diphosphate, the recombinant enzyme accepts simple indole derivatives with L-tryptophan as the best substrate, it is also active with tryptophan-containing cyclic dipeptides but with much lower conversion yields. No activity with geranyl or farnesyl diphosphate
-
-
?
additional information
?
-
-
no activity with 3-methylbutanyl diphosphate and 4-methyl-3-pentenyl diphosphate. Product identification with NMR spectroscopy
-
-
?
additional information
?
-
-
dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan
-
-
?
additional information
?
-
-
5-DMATS catalyzes regiospecific prenylation of analogues of ardeemin fumiquinazoline. Synthesis of ardeemin fumiquinazoline, a precursor of the multidrug resistance export pump inhibitor ardeemin, and its stereoisomers, LC-MS analysis of reaction products, overview
-
-
?
additional information
?
-
-
HR-ESI-MS and NMR product analysis. The enzyme catalyzes a regiospecific C-prenylation on the indole ring at C5 of L-Trp. No activity with L-m-tyrosine and L-tyrosine
-
-
?
additional information
?
-
-
no or poor activity with 5-methyl-DL-Trp, 5-bromo-DL-Trp, L-m-Tyr, and 6-[(2E)-pent-2-en-1-yl]-L-tryptophan. The enzyme catalyzes regiospecific prenylations of indolocarbazoles at the para-position of the indole N-atom. Molecular dynamics simulation experiments with a homologous model of 5-DMATS explain well its reactions with methylallyl and 2-pentenyl diphosphate. Comparison of bacterial and fungal alkylation/benzylation reactions by investigations on 5-DMATS from Aspergillus clavatus and 5-DMATSSc from Streptomyces coelicolor. Homology modelling of 5-DMATS, overview
-
-
?
additional information
?
-
-
no or poor activity with 5-methyl-DL-Trp, 5-bromo-DL-Trp, L-m-Tyr. No activity with 6-[(2E)-pent-2-en-1-yl]-L-tryptophan. The enzyme catalyzes regiospecific prenylations of indolocarbazoles at the para-position of the indole N-atom
-
-
?
additional information
?
-
-
5-DMATS catalyzes prenylation of L-tryptophan at C-5 of the indole ring
-
-
?
additional information
?
-
-
5-DMATS catalyzes prenylation of L-tryptophan at C-5 of the indole ring
-
-
?
additional information
?
-
-
5-DMATS catalyzes prenylation of L-tryptophan at C-5 of the indole ring
-
-
?
additional information
?
-
-
5-DMATSSc catalyzes regiospecific prenylation of analogues of ardeemin fumiquinazoline. Synthesis of ardeemin FQ, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, and its stereoisomers, LC-MS analysis of reaction products, overview
-
-
?
additional information
?
-
substrate specificity, overview. Molecular dynamics simulation experiments with a homologous model of 5-DMATS explain well its reactions with methylallyl and 2-pentenyl diphosphate. Comparison of bacterial and fungal alkylation/benzylation reactions by investigations on 5-DMATS from Aspergillus clavatus and 5-DMATSSc from Streptomyces coelicolor. Homology modelling of 5-DMATS, overview
-
-
?
additional information
?
-
substrate specificity, overview. Molecular dynamics simulation experiments with a homologous model of 5-DMATS explain well its reactions with methylallyl and 2-pentenyl diphosphate. Comparison of bacterial and fungal alkylation/benzylation reactions by investigations on 5-DMATS from Aspergillus clavatus and 5-DMATSSc from Streptomyces coelicolor. Homology modelling of 5-DMATS, overview
-
-
?
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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
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
C-5 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
the product is further processed to 5-dimethylallylindole-3-acetonitrile
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
additional information
?
-
-
dimethylallyltryptophan synthases (DMATSs) catalyze regiospecific transfer reactions of a prenyl moiety from dimethylallyl diphosphate to various positions of the indole ring of tryptophan
-
-
?
additional information
?
-
-
5-DMATS catalyzes prenylation of L-tryptophan at C-5 of the indole ring
-
-
?
additional information
?
-
-
5-DMATS catalyzes prenylation of L-tryptophan at C-5 of the indole ring
-
-
?
additional information
?
-
-
5-DMATS catalyzes prenylation of L-tryptophan at C-5 of the indole ring
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
additional information
the SCO7467-catalyzed prenylation reaction is Mg2+-independent
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
1-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.25
4-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.27
6-fluoro-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
1
6-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.47
7-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.67
DL-indole-3-lactate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.39
indole-3-propionate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.97
L-beta-homotryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.35
N-acetyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.4
trans-indole-3-acrylate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.131
2-pentenyl diphosphate
-
37°C, pH not specified in the publication
0.05
dimethylallyl diphosphate
pH 8.0, 30°C, recombinant enzyme
0.076
dimethylallyl diphosphate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.04
methylallyl diphosphate
-
37°C, pH not specified in the publication
additional information
additional information
-
Michaelis-Menten kinetics
-
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
-
kinetics analysis, overview
-
additional information
additional information
-
kinetics analysis, overview
-
additional information
additional information
-
kinetics analysis, overview
-
additional information
additional information
steady-state kinetic analysis demonstrates that the SCO7467 reaction follows Michaelis-Menten kinetics
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.059
1-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.29
4-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.29
6-fluoro-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.76
6-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.4
7-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.43
DL-indole-3-lactate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.39
indole-3-propionate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.15
L-beta-homotryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.1
N-acetyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.14
trans-indole-3-acrylate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.023
2-pentenyl diphosphate
-
37°C, pH not specified in the publication
0.4
dimethylallyl diphosphate
pH 8.0, 30°C, recombinant enzyme
1.3
dimethylallyl diphosphate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.005
methylallyl diphosphate
-
37°C, pH not specified in the publication
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.59
1-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.174
2-pentenyl diphosphate
-
37°C, pH not specified in the publication
1.16
4-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
1.074
6-fluoro-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.76
6-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.851
7-methyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
1.538
dimethylallyl diphosphate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.642
DL-indole-3-lactate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
1
indole-3-propionate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.155
L-beta-homotryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.136
methylallyl diphosphate
-
37°C, pH not specified in the publication
0.286
N-acetyl-DL-tryptophan
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.35
trans-indole-3-acrylate
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5