Information on EC 2.5.1.34 - 4-dimethylallyltryptophan synthase

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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
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 + 4-amino-5-(3-methylbut-2-en-1-yl)-L-tryptophan
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 + 4-methoxy-3a-(2-methylbut-3-en-2-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid + 4-methoxy-3a-(3-methylbut-2-en-1-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid + 4-methoxy-5-(3-methylbut-2-en-1-yl)-L-tryptophan + 4-methoxy-1-(3-methylbut-2-en-1-yl)-L-tryptophan
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 + 4-methyl-3a-(2-methylbut-3-en-2-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid + 4-methyl-3a-(3-methylbut-2-en-1-yl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid + 4-methyl-5-(3-methylbut-2-en-1-yl)-L-tryptophan + 4-methyl-1-(3-methylbut-2-en-1-yl)-L-tryptophan
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 + beta-homo-L-tryptophan
?
show the reaction diagram
-
51.5% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + bishomotryptophan
diphosphate + bis[4-(3-methylbut-2-enyl)]-L-homotryptophan
show the reaction diagram
-
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-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+
-
slight stimulation
Fe2+
-
activates
Li+
-
slight stimulation
Na+
-
slight stimulation
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
-
2,2'-bipyridyl
-
-
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
-
-
8-mercaptoquinoline
-
-
Acetylacetone
-
-
Chelating agents
-
in presence of excess of Ca2+
Co2+
5 mM, 50-80% inhibition
D-tryptophan
competitive with L-tryptophan
diphosphate
-
noncompetitive to dimethylallyl diphosphate
dithiothreitol
-
-
Fe2+
5 mM, 50-80% inhibition
L-4-(gamma,gamma-dimethylallyl)tryptophan
-
product inhibition, competitive to dimethylallyl diphosphate, noncompetitive to L-tryptophan
Mg2+
-
inhibition above 5 mM
Ni2+
5 mM, 50-80% inhibition
nitrilotriacetic acid
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.056
2-pentenyl diphosphate
-
37C, pH not specified in the publication
0.017
4-amino-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
0.25
4-methoxy-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
0.089
4-methyl-L-tryptophan
pH 8.0, 30C, 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, 37C, 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, 37C, wild-type enzyme
0.004 - 0.2
dimethylallyl diphosphate
0.011
ent-ardeemin fumiquinazoline
-
pH 7.5, 37C, 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, 37C
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, 37C, recombinant enzyme
0.47
L-o-tyrosine
-
pH 7.5, 37C, recombinant enzyme
0.0067 - 0.238
L-tryptophan
0.186 - 2.876
L-tryptophan methyl ester
0.04
methylallyl diphosphate
-
37C, 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, 30C
0.009
tryptophan
-
in presence of Ca2+
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.011
2-pentenyl diphosphate
-
37C, pH not specified in the publication
0.42
4-amino-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
1.3
4-methoxy-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
0.75
4-methyl-L-tryptophan
pH 8.0, 30C, 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
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.1267
7-methyl-DL-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.1033
alpha-methyl-DL-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.009
ardeemin fumiquinazoline
-
pH 7.5, 37C, wild-type enzyme
0.00106
cyclo-L-tryptophan-glycine
-
-
0.0017
cyclo-L-tryptophan-L-leucine
-
-
0.00113
cyclo-L-tryptophan-L-proline
-
-
0.0021
cyclo-L-tryptophan-L-tryptophan
-
-
0.0017
cyclo-L-tryptophan-L-tyrosine
-
-
0.009
dia-ardeemin fumiquinazoline
-
pH 7.5, 37C, wild-type enzyme
0.001 - 0.917
dimethylallyl diphosphate
0.0016
ent-ardeemin fumiquinazoline
-
pH 7.5, 37C, wild-type enzyme
0.2683
Indole-3-propionic acid
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.043
L-abrine
-
pH 7.5, 37C
0.3767
L-beta-homotryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
0.0065
L-m-tyrosine
-
pH 7.5, 37C, recombinant enzyme
0.29
L-o-tyrosine
-
pH 7.5, 37C, recombinant enzyme
0.001 - 60
L-tryptophan
0.117 - 0.1367
L-tryptophan methyl ester
0.009
methylallyl diphosphate
-
37C, pH not specified in the publication
0.252
N-methyl-L-tryptophan
-
in 50 mM Tris/HCl (pH 7.5) with 5 mM CaCl2
1.06
Nalpha-methyl-L-tryptophan
pH 7.4, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.198
2-pentenyl diphosphate
-
37C, pH not specified in the publication
25
4-amino-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
5.1
4-methoxy-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
8.5
4-methyl-L-tryptophan
pH 8.0, 30C, recombinant His-tagged 4-DMATS
-
24
cyclo-L-tryptophan-glycine
-
-
122
cyclo-L-tryptophan-L-leucine
-
-
21
cyclo-L-tryptophan-L-proline
-
-
66.5
cyclo-L-tryptophan-L-tryptophan
-
-
48
cyclo-L-tryptophan-L-tyrosine
-
-
0.0072
L-m-tyrosine
-
pH 7.5, 37C, recombinant enzyme
0.617
L-o-tyrosine
-
pH 7.5, 37C, recombinant enzyme
39.33 - 3100
L-tryptophan
0.232
methylallyl diphosphate
-
37C, pH not specified in the publication
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0404
D-tryptophan
pH 7.4, 30C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.309
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 7.5
-
-
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)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34000
-
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
-
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
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
purified enzyme, pH 7.5, 4 h, 20% activity remaining
50
-
1 h, complete loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
repeated thawing and freezing greatly accelerates denaturation
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 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
-
-20C, 50% loss of activity after several weeks
-
-20C, 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