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Information on EC 2.5.1.80 - 7-dimethylallyltryptophan synthase
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EC Tree
2.5.1.80 7-dimethylallyltryptophan synthaseIUBMB Comments
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 prenyl diphosphate as the prenyl donor.
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Word Map
- 2.5.1.80
-
prenylation
- indole
- drug development
-
dmapp
- fumigatus
-
o-prenyltransferase
- synthesis
-
regioselective
- dipeptide
- fgapt2
-
his6-fusion
-
o-prenylated
-
c-prenylations
- maculans
-
leptosphaeria
- neosartorya
-
tryptophan-containing
- biotechnology
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
7-dimethylallyltryptophan synthase, 7-dimethylallyl tryptophan synthase, tryptophan c7-prenyltransferase, cak41583, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
7-dimethylallyl tryptophan synthase
7-DMATS
dimethylallyltryptophan synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
catalytic reaction mechanism involving Glu138, overview
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alkenyl group transfer
-
-
-
-
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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 prenyl diphosphate as the prenyl donor.
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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 + 5-(pent-2-enyl)-L-tryptophan
C-5 prenylation
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 5-benzyl-L-tryptophan
C-5 prenylation
-
-
?
dimethylallyl diphosphate + 1,6-dihydroxynaphthalene
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,6-diol
-
-
-
-
?
dimethylallyl diphosphate + 1,7-dihydroxynaphthalene
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,7-diol
-
-
-
-
?
dimethylallyl diphosphate + 1-methyl-DL-tryptophan
diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-7-(3-methylbut-2-enyl)-L-tryptophan
-
35.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 1-naphthol
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalen-1-ol
-
-
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
?
-
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-4-(3-methylbut-2-enyl)-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-DL-7-(gamma,gamma-dimethylallyl)tryptophan
-
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
-
-
-
-
?
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
-
-
1-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol is the major product
-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-(3-methylbut-2-enyl)-L-tyrosine
C-4 prenylation
-
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-phenylalanine
C-4 prenylation
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-4-methyl-DL-tryptophan
dimethylallyl diphosphate + 5-bromo-DL-tryptophan
diphosphate + 5-bromo-7-(3-methylbut-2-enyl)-DL-tryptophan
-
7.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-bromo-L-tryptophan
diphosphate + 5-bromo-4-(3-methylbut-2-enyl)-L-tryptophan
low activity
-
-
?
dimethylallyl diphosphate + 5-fluoro-L-tryptophan
diphosphate + 5-fluoro-7-(3-methylbut-2-enyl)-L-tryptophan
-
10.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-7-(3-methylbut-2-enyl)-L-tryptophan
-
26.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
?
-
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
-
13.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methoxy-DL-tryptophan
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
?
-
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-4-(3-methylbut-2-enyl)-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
-
74.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-4-(3-methylbut-2-enyl)-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-7-(3-methylbut-2-enyl)-DL-tryptophan
-
33.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
?
-
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-4-(3-methylbut-2-enyl)-DL-tryptophan
low activity
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
-
19.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-DL-tryptophan + ?
-
0.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (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
dimethylallyl diphosphate + biochanin A
diphosphate + gancaonin A
-
15.9% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + cyclo-L-7-(3-methylbut-2-enyl)-Trp-Gly
-
1.8% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + D-tryptophan
?
-
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 + 4-(3-methylbut-2-enyl)-D-tryptophan
low activity
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-7-(3-methylbut-2-enyl)-tryptophan
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 + (1R,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
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 + (1S,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
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 7-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
-
4.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
diphosphate + (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
-
-
-
?
dimethylallyl diphosphate + eriodictyol
diphosphate + 6-(3-methylbut-2-enyl)eriodictyol
-
19.0% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + genistein
diphosphate + wighteone
-
10.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + hesperetin
diphosphate + sigmoidin B
-
1.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + indole-3-acetic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-acetic acid
-
10.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-butyric acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-butyric acid
-
9.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-propionic acid
-
8.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-pyruvic acid
-
4.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
?
-
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
dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 4-(3-methylbut-2-enyl)-L-o-tyrosine
C-4 prenylation
4-dimethylallyl-L-o-tyrosine
-
?
dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine
C-5 prenylation, proposed reaction mechanism, overview
-
-
?
dimethylallyl diphosphate + L-Trp-Gly
diphosphate + L-7-(3-methylbut-2-enyl)-Trp-Gly
-
10.9% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan
?
-
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)
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-7-(3-methylbut-2-enyl)-tryptophan
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + L-7-(gamma,gamma-dimethylallyl)tryptophan hydroxamate
-
4.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
dimethylallyl diphosphate + L-tyrosine
diphosphate + 5-[(2E)-pent-2-en-1-yl]-L-tryptophan
O-4 prenylation
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-N-acetyl-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-DL-7-(gamma,gamma-dimethylallyl)tryptophan
-
7.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-7-(gamma,gamma-dimethylallyl)tryptophan
i.e. L-abrine
82.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + naringenin
diphosphate + 6-(3-methylbut-2-enyl)naringenin
-
1.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + phloretin
diphosphate + 6-dimethylallyl-5,7,9,1'-tetrahydroxydihydrochalcone
-
17.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + tryptamine
?
-
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)
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 4-(but-2-enyl)-L-tryptophan
C-4 and C-5 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(but-2-enyl)-L-tryptophan
C-4 and C-5 prenylation
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
-
89.4% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-4-methyl-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-4-methyl-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methoxy-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methoxy-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
-
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (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
-
-
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (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
-
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-7-(3-methylbut-2-enyl)-tryptophan
-
11.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-7-(3-methylbut-2-enyl)-tryptophan
-
15.5% of the activity with L-tryptophan
-
?
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 + (1R,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
-
-
-
?
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 + (1R,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
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
?
-
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)
-
-
?
dimethylallyl diphosphate + L-abrine
?
-
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
diphosphate + 7-(3-methylbut-2-enyl)-L-beta-homotryptophan
-
28.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-beta-homotryptophan
-
-
-
?
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 + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
7-DMATS accept L-tryptophan as substrate and prenylate it at C-7
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
7-DMATS accept L-tryptophan as substrate and prenylate it at C-7
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
L-tryptophan is the preferred substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
C-7 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
the enzyme catalyzes C7-prenylation of the indole ring
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-7-(3-methylbut-2-enyl)-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-7-(3-methylbut-2-enyl)-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
7.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
-
-
-
?
dimethylallyl diphosphate + tryptamine
diphosphate + 7-(3-methylbut-2-enyl)-tryptamine
-
7.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + tryptamine
diphosphate + 7-(3-methylbut-2-enyl)-tryptamine
-
-
-
-
?
additional information
?
-
-
7-DMATS catalyzes regio- and stereospecific prenylations, assay conditions with different substrates, detailed overview
-
-
?
additional information
?
-
-
7-DMATS catalyzes regio- and stereospecific prenylations, assay conditions with different substrates, detailed overview
-
-
?
additional information
?
-
no substrate: geranyl diphosphate, L-phenylalanine, L-tyrosine
-
-
?
additional information
?
-
-
no substrate: geranyl diphosphate, L-phenylalanine, L-tyrosine
-
-
?
additional information
?
-
-
7-DMATS substrate specificity with flavonoid compounds, overview. Chalcones, isoflavonoids, and flavanones are much better accepted than flavones and flavonols
-
-
?
additional information
?
-
-
substrate specificity of 7-DMATS, overview
-
-
?
additional information
?
-
7-DMATS catalyzes mainly regiospecific prenylation at C-7 of analogues of ardeemin fumiquinazoline, which is also observed for its natural substrate L-tryptophan. Synthesis of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, and its stereoisomers, LC-MS analysis of reaction products, overview
-
-
?
additional information
?
-
enzyme 7-DMATS also accepts L-tyrosine as substrate and converts it to an O-prenylated derivative, cf. EC 2.5.1.122. 7-DMATS is also able to take L-tyrosine and two derivatives thereof as substrates and catalyzes the same O- or N-prenylation
-
-
?
additional information
?
-
HR-ESI-MS and NMR product analysis. No activity with L-3-tyrosine
-
-
?
additional information
?
-
no activity with 7-methyl-DL-tryptophan, alpha-methyl-L-tyrosine, L-m-tyrosine, and D-tyrosine. The enzyme is also active with hydroxynaphthalenes which it prenylates at C-4 or C-1, overview
-
-
?
additional information
?
-
the tryptophan C7-prenyltransferase 7-DMATS from Aspergillus fumigatus accepts very poorly methylallyl diphosphate and 2-pentenyl diphosphate as substrates, it shows low activity in the presence of unnatural dimethylallyl diphosphate analogues
-
-
?
additional information
?
-
7-DMATS catalyzes mainly regiospecific prenylation at C-7 of analogues of ardeemin fumiquinazoline, which is also observed for its natural substrate L-tryptophan. Synthesis of ardeemin fumiquinazoline, a precursor of the multidrug resistance (MDR) export pump inhibitor ardeemin, and its stereoisomers, LC-MS analysis of reaction products, overview
-
-
?
additional information
?
-
the enzyme catalyzes O-prenylation of L-tyrosine, EC 2.5.1.122, and also accepts 4-amino-L-phenylalanine for an N-prenylation and L-tryptophan for a C7-prenylation, EC 2.5.1.80. HRMS analysis of the enzyme product, overviews. 7-Prenylation substrate specificity, overview. No activity with D-tryptophan
-
-
?
additional information
?
-
-
the enzyme catalyzes O-prenylation of L-tyrosine, EC 2.5.1.122, and also accepts 4-amino-L-phenylalanine for an N-prenylation and L-tryptophan for a C7-prenylation, EC 2.5.1.80. HRMS analysis of the enzyme product, overviews. 7-Prenylation substrate specificity, overview. No activity with D-tryptophan
-
-
?
additional information
?
-
-
7-DMATSNeo accepts not only L-tryptophan but also simple indole derivatives as substrates. The retention of the amino group of L-tryptophan appears to be an essential factor for molecular recognition by 7-DMATSNeo. No or poor activity with D-tryptophan, 5-hydroxy-L-tryptophan, indole-3-propionic acid, indole-3-pyruvic acid, DL-indole-3-lactic acid, glycyl-L-tryptophan, and cyclo(glycyl-L-tryptophan). No activity with 5-hydoroxy-L-tryptophan, 7-methyl-DL-tryptophan, 6-fluoro-DL-tryptophan, and 1-methyl-DL-tryptophan. Mass spectrometric product identification and analysis, 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 + 7-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
C-7 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
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+
Mg2+
additional information
additional information
addition of divalent cations is not required
additional information
no significant effects on enzyme activity by K+, Na+, Mg2+, Mn2+, Co2+, or EDTA
additional information
-
no significant effects on enzyme activity by K+, Na+, Mg2+, Mn2+, Co2+, or EDTA
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
phloretin
-
shows substrate inhibition at 1 mM or higher concentrations
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.14
L-tryptophan
-
pH and temperature not specified in the publication
additional information
additional information
-
kinetics analyis, overview
-
additional information
additional information
-
kinetics analyis, overview
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.23
L-tryptophan
-
pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE