Information on EC 2.5.1.34 - 4-dimethylallyltryptophan synthase

Word Map on EC 2.5.1.34
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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.5.1.34
-
RECOMMENDED NAME
GeneOntology No.
4-dimethylallyltryptophan synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alkenyl group transfer
Friedel-Crafts alkylation
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chanoclavine I aldehyde biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:L-tryptophan 4-dimethylallyltransferase
-
CAS REGISTRY NUMBER
COMMENTARY hide
55127-01-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Claviceps sp.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
metabolism
physiological function
additional information
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 + 5-(2-trans-pentenyl)-L-tryptophan
show the reaction diagram
-
very low activity, the alkylation shifts from C-4 to C-5 for FgaPT2, which can be explained by the longer chain length and thus deeper extension of 2-pentenyl diphosphate into the reaction chamber in comparison to that of dimethylallyl diphosphate, so that C-1' of the alkyl residue is closer to C-5 than C-4 in FgaPT2
-
-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 5-(pent-2-enyl)-L-tryptophan
show the reaction diagram
-
C-5 prenylation
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 5-benzyl-L-tryptophan
show the reaction diagram
-
C-5 prenylation
-
-
?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 1-naphthol
diphosphate + ?
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
?
show the reaction diagram
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
1.6% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-DL-4-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
-
1.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 4-amino-L-Phe
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-Phe
show the reaction diagram
-
C-3 prenylation
-
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-phenylalanine
show the reaction diagram
-
low activity with the wild-type enzyme, higher activity with the enzyme mutant K174F
-
-
?
dimethylallyl diphosphate + 4-amino-L-tryptophan
diphosphate + 9
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 4-amino-L-tryptophan
diphosphate + ?
show the reaction diagram
an alternate substrate, giving normal prenylation at C5 and C7, shows 0.81% of the activity with L-tryptophan
the reaction with 4-methoxytryptophan gives five products, analysis, overview
-
?
dimethylallyl diphosphate + 4-methoxy-L-tryptophan
diphosphate + 5 + 6 + 7 + 8
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 4-methoxy-L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)4-methoxy-L-tryptophan
show the reaction diagram
an alternate substrate, giving normal prenylation at C5 as the major product, shows 0.17% of the activity with L-tryptophan
the reaction with 4-methoxytryptophan gives four products, analysis, overview
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-DL-tryptophan + ?
show the reaction diagram
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 4-methyl-L-tryptophan
diphosphate + 1 + 2 + 3 + 4
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 4-methyl-L-tryptophan
diphosphate + ?
show the reaction diagram
an alternate substrate and competitive inhibitor, shows 0.28% of the activity with L-tryptophan
the reaction with 4-methyltryptophan gives four products, analysis, overview
-
?
dimethylallyl diphosphate + 5-bromo-DL-tryptophan
diphosphate + 5-bromo-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-fluoro-L-tryptophan
diphosphate + 5-fluoro-4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-hydroxy-L-tryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
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-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
0.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-D-tryptophan
show the reaction diagram
-
0.5% of the activity 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 + 4-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 5-methyl-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 5-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
0.2% 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 + 4-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 6-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
16.3% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan + ?
show the reaction diagram
-
16.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 7-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-7-methyl-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + alpha-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-alpha-methyl-DL-tryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (1S,4R)-4-methyl-1-[[4-(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-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + bishomotryptophan
diphosphate + bis[4-(3-methylbut-2-enyl)]-L-homotryptophan
show the reaction diagram
Claviceps sp.
-
2% of the activity with tryptophan
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-glycine
diphosphate + cyclo-L-4-dimethylallyltryptophan-glycine
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-leucine
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-leucine
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-proline
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-proline
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-tryptophan
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-tryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-tyrosine
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-tyrosine
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + D-tryptophan
?
show the reaction diagram
dimethylallyl diphosphate + D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
show the reaction diagram
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-4-(3-methylbut-2-enyl)-tryptophan
show the reaction diagram
-
9.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
diphosphate + (1R,4R)-4-methyl-1-[[4-(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-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
diphosphate + (1S,4S)-4-methyl-1-[[4-(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-[[5-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
?
show the reaction diagram
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 4-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
show the reaction diagram
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
diphosphate + (1R,4S)-4-methyl-1-[[4-(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-[[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
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + indole-3-acetic acid
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + indole-3-acetic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-acetic acid
show the reaction diagram
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-butyric acid
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + indole-3-butyric acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-butyric acid
show the reaction diagram
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid
?
show the reaction diagram
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-propionic acid
show the reaction diagram
dimethylallyl diphosphate + indole-3-pyruvic acid
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-pyruvic acid
show the reaction diagram
dimethylallyl diphosphate + L-abrine
?
show the reaction diagram
dimethylallyl diphosphate + L-beta-homo-L-tryptophan
?
show the reaction diagram
-
51.5% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
?
show the reaction diagram
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-beta-homotryptophan
show the reaction diagram
-
51.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-homotryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + L-m-tyrosine
diphosphate + 4-(3-methylbut-2-enyl)-L-m-tyrosine + 6-(3-methylbut-2-enyl)-L-m-tyrosine
show the reaction diagram
-
C-4 and C-6 prenylation, proposed reaction mechanism, overview
-
-
?
dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine
show the reaction diagram
-
C-5 prenylation, proposed reaction mechanism, overview
-
-
?
dimethylallyl diphosphate + L-tryptophan
?
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-dimethylallyl-L-tryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(3-methylbut-2-enyl)-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan hydroxamate
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan hydroxamate
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan hydroxamate
show the reaction diagram
-
22.4% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
show the reaction diagram
-
7.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + L-Tyr
diphosphate + 3-(3-methylbut-2-enyl)-L-Tyr
show the reaction diagram
-
C-3 prenylation
3-dimethylallyl-L-tyrosine
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
show the reaction diagram
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-DL-4-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + N-methyl-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-N-methyl-L-tryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-4-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
dimethylallyl diphosphate + serotonin
diphosphate + 4-(3-methylbut-2-enyl)-serotonin
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + tryptamin
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + tryptamin
diphosphate + 4-(3-methylbut-2-enyl)-tryptamin
show the reaction diagram
-
-
-
-
?
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 + 4-(3-methylbut-2-enyl)-tryptamine
show the reaction diagram
dimethylallyl diphosphate indole-3-lactic acid
?
show the reaction diagram
-
10.5% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate indole-3-pyruvic acid
?
show the reaction diagram
-
29.4% of the activity with L-Trp
-
-
?
dimethylallyl S-thiolodiphosphate + L-tryptophan
?
show the reaction diagram
-
dimethylallyl S-thiolodiphosphate serves as an analogue to the natural substrate, dimethylallyl diphosphate
-
-
?
diphosphate + 7-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-7-methyl-DL-tryptophan
show the reaction diagram
-
-
-
-
?
geranyl diphosphate + L-tryptophan
diphosphate + ?
show the reaction diagram
very low activity, 0.7% of the activity with dimethylallyl diphosphate
-
-
ir
isopentenyl diphosphate + L-tryptophan
diphosphate + ?
show the reaction diagram
3.4% of the activity with dimethylallyl diphosphate
-
-
ir
methylallyl diphosphate + L-tryptophan
diphosphate + 4-(2-trans-butenyl)-L-tryptophan + 5-(2-trans-butenyl)-L-tryptophan
show the reaction diagram
-
very low activity
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 4-(but-2-enyl)-L-tryptophan
show the reaction diagram
-
C-4 and C-5 prenylation
-
-
?
methylallyl diphosphate + L-tryptophan
diphosphate + 5-(but-2-enyl)-L-tryptophan
show the reaction diagram
-
C-4 and C-5 prenylation
-
-
?
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 + 4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cu2+
Claviceps sp.
-
slight stimulation
Fe2+
Claviceps sp.
-
activates
Li+
Claviceps sp.
-
slight stimulation
Na+
Claviceps sp.
-
slight stimulation
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
Claviceps sp.
-
-
2,2'-bipyridyl
Claviceps sp.
-
-
4-methyl-DL-tryptophan
a competitive substrate inhibitor
4-methyltryptophan
4-methyltryptophan is a competitive dead-end analogue of tryptophan used in kinetic studies of 4-DMATS
8-hydroxyquinoline
Claviceps sp.
-
-
8-mercaptoquinoline
Claviceps sp.
-
-
Acetylacetone
Claviceps sp.
-
-
Chelating agents
Claviceps sp.
-
in presence of excess of Ca2+
Co2+
5 mM, 50-80% inhibition
Co3+
Claviceps sp.
-
-
D-tryptophan
competitive with L-tryptophan
diphosphate
Claviceps sp.
-
noncompetitive to dimethylallyl diphosphate
dithiothreitol
Claviceps sp.
-
-
Fe2+
5 mM, 50-80% inhibition
Hg2+
Claviceps sp.
-
-
L-4-(gamma,gamma-dimethylallyl)tryptophan
Claviceps sp.
-
product inhibition, competitive to dimethylallyl diphosphate, noncompetitive to L-tryptophan
Mg2+
Claviceps sp.
-
inhibition above 5 mM
Ni2+
5 mM, 50-80% inhibition
nitrilotriacetic acid
Claviceps sp.
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.056
2-pentenyl diphosphate
-
37°C, pH not specified in the publication
0.017
4-amino-L-tryptophan
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
0.25
4-methoxy-L-tryptophan
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
0.089
4-methyl-L-tryptophan
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
-
0.3031 - 0.509
5-hydroxy-L-tryptophan
0.039 - 0.416
5-methyl-DL-tryptophan
0.103
6-methyl-DL-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.129
7-methyl-DL-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.35
alpha-methyl-DL-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.032
ardeemin fumiquinazoline
-
pH 7.5, 37°C, wild-type enzyme
-
0.439
cyclo-L-tryptophan-glycine
-
-
0.14
cyclo-L-tryptophan-L-leucine
-
-
0.536
cyclo-L-tryptophan-L-proline
-
-
0.326
cyclo-L-tryptophan-L-tryptophan
-
-
0.354
cyclo-L-tryptophan-L-tyrosine
-
-
0.055
dia-ardeemin fumiquinazoline
-
pH 7.5, 37°C, wild-type enzyme
-
0.004 - 0.2
dimethylallyl diphosphate
0.011
ent-ardeemin fumiquinazoline
-
pH 7.5, 37°C, wild-type enzyme
-
0.558
Indole-3-propionic acid
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.081
L-abrine
-
pH 7.5, 37°C
0.242
L-beta-homotryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.9
L-m-tyrosine
-
pH 7.5, 37°C, recombinant enzyme
-
0.47
L-o-tyrosine
-
pH 7.5, 37°C, recombinant enzyme
-
0.0067 - 0.238
L-tryptophan
0.186 - 2.876
L-tryptophan methyl ester
0.04
methylallyl diphosphate
-
37°C, pH not specified in the publication
0.13
N-methyl-L-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.106
Nalpha-methyl-L-tryptophan
pH 7.4, 30°C
0.009
tryptophan
Claviceps sp.
-
in presence of Ca2+
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.011
2-pentenyl diphosphate
Aspergillus fumigatus
-
37°C, pH not specified in the publication
0.42
4-amino-L-tryptophan
Claviceps purpurea
M1WA41
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
1.3
4-methoxy-L-tryptophan
Claviceps purpurea
M1WA41
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
0.75
4-methyl-L-tryptophan
Claviceps purpurea
M1WA41
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
-
0.165 - 0.56
5-hydroxy-L-tryptophan
0.0683 - 0.125
5-methyl-DL-tryptophan
0.0533
6-methyl-DL-tryptophan
Aspergillus fumigatus
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.1267
7-methyl-DL-tryptophan
Aspergillus fumigatus
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.1033
alpha-methyl-DL-tryptophan
Aspergillus fumigatus
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.009
ardeemin fumiquinazoline
Aspergillus fumigatus
-
pH 7.5, 37°C, wild-type enzyme
-
0.00106
cyclo-L-tryptophan-glycine
Aspergillus fumigatus
-
-
0.0017
cyclo-L-tryptophan-L-leucine
Aspergillus fumigatus
-
-
0.00113
cyclo-L-tryptophan-L-proline
Aspergillus fumigatus
-
-
0.0021
cyclo-L-tryptophan-L-tryptophan
Aspergillus fumigatus
-
-
0.0017
cyclo-L-tryptophan-L-tyrosine
Aspergillus fumigatus
-
-
0.009
dia-ardeemin fumiquinazoline
Aspergillus fumigatus
-
pH 7.5, 37°C, wild-type enzyme
-
0.001 - 0.917
dimethylallyl diphosphate
0.0016
ent-ardeemin fumiquinazoline
Aspergillus fumigatus
-
pH 7.5, 37°C, wild-type enzyme
-
0.2683
Indole-3-propionic acid
Aspergillus fumigatus
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.043
L-abrine
Aspergillus fumigatus
-
pH 7.5, 37°C
0.3767
L-beta-homotryptophan
Aspergillus fumigatus
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.0065
L-m-tyrosine
Aspergillus fumigatus
-
pH 7.5, 37°C, recombinant enzyme
-
0.29
L-o-tyrosine
Aspergillus fumigatus
-
pH 7.5, 37°C, recombinant enzyme
-
0.001 - 60
L-tryptophan
0.117 - 0.1367
L-tryptophan methyl ester
0.009
methylallyl diphosphate
Aspergillus fumigatus
-
37°C, pH not specified in the publication
0.252
N-methyl-L-tryptophan
Aspergillus fumigatus
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
1.06
Nalpha-methyl-L-tryptophan
Malbranchea aurantiaca
B1A4C4
pH 7.4, 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.198
2-pentenyl diphosphate
Aspergillus fumigatus
-
37°C, pH not specified in the publication
15354
25
4-amino-L-tryptophan
Claviceps purpurea
M1WA41
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
42431
5.1
4-methoxy-L-tryptophan
Claviceps purpurea
M1WA41
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
42430
8.5
4-methyl-L-tryptophan
Claviceps purpurea
M1WA41
pH 8.0, 30°C, recombinant His-tagged 4-DMATS
22968
24
cyclo-L-tryptophan-glycine
Aspergillus fumigatus
-
-
40085
122
cyclo-L-tryptophan-L-leucine
Aspergillus fumigatus
-
-
40084
21
cyclo-L-tryptophan-L-proline
Aspergillus fumigatus
-
-
40086
66.5
cyclo-L-tryptophan-L-tryptophan
Aspergillus fumigatus
-
-
40082
48
cyclo-L-tryptophan-L-tyrosine
Aspergillus fumigatus
-
-
40083
0.0072
L-m-tyrosine
Aspergillus fumigatus
-
pH 7.5, 37°C, recombinant enzyme
214009
0.617
L-o-tyrosine
Aspergillus fumigatus
-
pH 7.5, 37°C, recombinant enzyme
214008
39.33 - 3100
L-tryptophan
119
0.232
methylallyl diphosphate
Aspergillus fumigatus
-
37°C, pH not specified in the publication
15353
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0404
D-tryptophan
pH 7.4, 30°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.309
Claviceps sp.
-
-
0.35
Claviceps sp.
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 7.5
Claviceps sp.
-
-
8
assay at; assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
-
assay at room temperature
30 - 37
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Neosartorya fischeri (strain ATCC 1020 / DSM 3700 / CBS 544.65 / FGSC A1164 / JCM 1740 / NRRL 181 / WB 181)
Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSC A1100)
Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSC A1100)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34000
Claviceps sp.
-
2 * 34000, SDS-PAGE
50000
-
determined by SDS-PAGE
51000
1 * 52000, calculated, 1 * 51000, SDS-PAGE, His-tagged protein
51824
-
x * 51824, calculation from nucleotide sequence
52000
1 * 52000, calculated, 1 * 51000, SDS-PAGE, His-tagged protein
52500
2 * 52500, about, amino acid sequence calculation, 2 * 57000, recombinant His6-tagged enzyme, SDS-PAGE
53000
-
alpha2, 2 * 53000, SDS-PAGE
54000
-
calculated for His6-7-DMATS
61600
gel filtration
65000
-
determined by gel filtration
86000 - 91000
gel filtration
105000
-
gel filtration
210000
Claviceps sp.
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 51824, calculation from nucleotide sequence
monomer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis
-
the crystal structure of FgaPT2 (4-DMATS) is determined as a complex with its aromatic substrate L-tryptophan and with dimethylallyl S-thiolodiphosphate (DMSPP), an analogue of its isoprenoid substrate dimethylallyl diphosphate, X-ray structural analysis and three-dimensional structural modeling
-
x-ray structure of DMATS, determined at a resolution of 1.76 A is reported. A complex of DMATS with its substrate L-tryptophan and with an analogue of its isoprenoid substrate dimethylallyl diphosphate reveals the structural basis of this enzyme-catalyzed Friedel-Crafts reaction, showing strict regiospecificity for position 4 of the indole nucleus of tryptophan as well as unusual independence of the presence of Mg2+ ions. The 3D structure of DMATS belongs to a rare alpha/beta barrel fold, called prenyltransferase barrel, that is present in a small group of bacterial enzymes with no sequence similarity to DMATS
-
-
Claviceps sp.
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
purified enzyme, pH 7.5, 4 h, 20% activity remaining
50
Claviceps sp.
-
1 h, complete loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
repeated thawing and freezing greatly accelerates denaturation
Claviceps sp.
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 10 mM Tris-HCl, pH 8.0, 20 mM CaCl2, 20 mM 2-mercaptoethanol, 10% glycerol, 2 mg/ml enzyme concentration, stable for 1 week
Claviceps sp.
-
-20°C, 50% loss of activity after several weeks
Claviceps sp.
-
-20°C, glycerol-containing buffer, stable for more than 6 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
His6-7-DMATS is purified with Ni-NTA agarose
-
Ni-NTA agarose chromatography
-
recombinant enzyme
-
recombinant His-tagged 4-DMATS from Escherichia coli strain BL21 or Saccharomyces cerevisiae strain INVSc1 by nickel affinity chromatography
recombinant His-tagged 4-DMATS from Escherichia coli strain BL21 Star (DE3) by nickel affinity chromatography and dialysis
recombinant His6-tagged enzyme to near homogeneity from Saccharomyces cerevisiae by nickel affinity chromatography
using Ni-NTA chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as a His-tagged fusion protein
-
expressed as a recombinant protein
-
expressed in Escherichia coli BL21(DE3) pLysS cells
-
expression in Escherichia coli
expression in Saccharomyces cerevisiae
-
expression of His-tagged 4-DMATS in Escherichia coli strain BL21 Star (DE3); recombinant expression of the soluble enzyme in Escherichia coli strain BL21 Star™ (DE3)
expression of His-tagged 4-DMATS in Escherichia coli strains XL1 Blue or M15 or in Saccharomyces cerevisiae strain INVSc1
gene 4-DMATS, sequence comparison
-
gene 4-DMTAS, recombinant overexpression in Escherichia coli strain BL21 (DE3)pLysS
-
gene fgaPT2, DNA and amino acid sequence determination and analysis, overexpression of His6-tagged enzyme in Saccharomyces cerevisiae INVSc1
into pGEM-T and subsequently into pQE60 for expression in Escherichia coli XL1 Blue MRF cells
-
overexpressed in Escherichia coli as a C-terminal His-tagged fusion protein
-
recombinant expression
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
E89Q
-
site-directed mutagenesis, the mutant shows a 400fold reduction in kcat compared to the wild-type enzyme
I80F
-
site-directed mutagenesis
K174E
-
site-directed mutagenesis
K174F
-
site-directed mutagenesis, the FgaPT2 mutant shows a much higher catalytic activity toward L-tyrosine than L-tryptophan compared to the wild-type. The single mutation on the key amino acid switches the tryptophan C4-prenyltransferase to a tyrosine C3-prenylating enzyme
K174F/R244E
-
site-directed mutagenesis
K174W
-
site-directed mutagenesis
K174Y
-
site-directed mutagenesis
M328L
-
site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme
R244D
-
site-directed mutagenesis
R244E
-
site-directed mutagenesis
R244N
-
site-directed mutagenesis
R244Q
-
site-directed mutagenesis
T102C
-
site-directed mutagenesis
T102G
-
site-directed mutagenesis
T102R
-
site-directed mutagenesis
T102S
-
site-directed mutagenesis
T102V
-
site-directed mutagenesis
Y398F
-
site-directed mutagenesis, the FgaPT2 mutant shows increased activity with L-tyrosine compared to the wild-type enzyme
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
-
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
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