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Information on EC 2.5.1.34 - 4-dimethylallyltryptophan synthase
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EC Tree
2.5.1.34 4-dimethylallyltryptophan synthaseSpecify your search results
Word Map
- 2.5.1.34
- prenyltransferases
- indole
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ergot
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dmapp
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tryptophan-containing
-
disaster
- claviceps
-
o-prenyltransferase
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o-prenylated
- neosartorya
-
hydroxynaphthalenes
-
earthquake
-
friedel-crafts
- anapt
-
c-prenylation
-
clavine
- ftmpt1
- synthesis
- biotechnology
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
fgapt2, dmats, dimethylallyltryptophan synthase, 4-dimethylallyltryptophan synthase, dmaw2, dmat synthetase, dmat synthase, dimethylallyl-tryptophan synthase, 4-(gamma,gamma-dimethylallyl)tryptophan synthase, 4-dmats, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-(gamma,gamma-dimethylallyl)tryptophan synthase
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4-DMATS
dimethylallylpyrophosphate:L-tryptophan dimethylallyltransferase
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dimethylallylpyrophosphate:tryptophan dimethylallyl transferase
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dimethylallylpyrophosphate:tryptophan dimethylallyltransferase
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dimethylallyltransferase, tryptophan
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dimethylallyltryptophan synthase
dimethylallyltryptophan synthetase
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DMAT synthase
DMAT synthetase
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DmaW2
FgaPT2
IfgA
MaPT
Proq05g069320
tryptophan C4-prenyltransferase FgaPT2
DMAT synthase
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FgaPT2
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
sequential mechanism
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
random sequential mechanism
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
stereochemistry, direct attack of dimethylallyl diphosphate on C-4 of the indole
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
catalytic reaction mechanism, overview
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
studies are presented that strongly support the dissociative mechanism for the DMAT synthase reaction. The observation of positional isotope exchange (PIX) in isotopically labeled DMAPP provides evidence for the existence of a dimethylallyl carbocation intermediate
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
ability of dimethylallyltryptophan synthase to prenylate at five different sites on the indole nucleus, with normal and reverse prenylation at one of the sites, is consistent with a dissociative electrophilic alkylation of the indole ring, where orientation of the substrates within the active site and substituent electronic effects determine the position and type of prenylation
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
Cope mechanism for the reaction catalyzed by DMAT synthase, overview
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
enzyme-catalyzed sigmatropic process in the C-4 prenylation of indole alkaloids, an initial reverse prenylation of tryptophan at C-3 with dimethylallyl diphosphate, the subsequent Cope rearrangement shifts the prenyl moiety to the C-4 position and re-aromatization gives dimethylallyltryptophan, reaction mechanism,overview
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
reaction mechanism and substrate specificity, overview
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
SN1-like mechanism involving a discrete carbocation intermediate involving initial ion pair formation followed by a reverse prenylation at the nucleophilic C-3 position, detailed overview
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
the mechanism of this enzyme-catalyzed FriedelCrafts reaction represents strict regioselectivity at the C4 position of the indole ring of L-tryptophan, proposed reaction mechanism for Aspergillus fummigatus FgaPT2 involving Glu89 and Lys174
dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
sequential mechanism
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
random sequential mechanism
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alkenyl group transfer
alkenyl group transfer
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:L-tryptophan 4-dimethylallyltransferase
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CAS REGISTRY NUMBER
COMMENTARY
55127-01-0
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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-(2-trans-pentenyl)-L-tryptophan
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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
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-
?
2-pentenyl diphosphate + L-tryptophan
diphosphate + 5-(pent-2-enyl)-L-tryptophan
C-5 prenylation
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?
4-dimethylallyl-indole-3-lactic acid
?
10.5% of the activity with L-Trp
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?
4-dimethylallyl-indole-3-pyruvic acid
?
29.4% of the activity with L-Trp
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?
benzyl diphosphate + L-tryptophan
diphosphate + 5-benzyl-L-tryptophan
C-5 prenylation
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?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
1.6% of the activity with L-Trp
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?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-DL-4-(gamma,gamma-dimethylallyl)tryptophan
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1.6% of the yield with L-tryptophan
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?
dimethylallyl diphosphate + 4-amino-L-Phe
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-Phe
C-3 prenylation
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?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-phenylalanine
low activity with the wild-type enzyme, higher activity with the enzyme mutant K174F
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?
dimethylallyl diphosphate + 4-amino-L-tryptophan
diphosphate + 4-amino-5-(3-methylbut-2-en-1-yl)-L-tryptophan
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-
-
?
dimethylallyl diphosphate + 4-amino-L-tryptophan
diphosphate + ?
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
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?
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
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?
dimethylallyl diphosphate + 4-methoxy-L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)4-methoxy-L-tryptophan
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
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?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-DL-tryptophan + ?
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0.2% of the yield with L-tryptophan
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?
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
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?
dimethylallyl diphosphate + 4-methyl-L-tryptophan
diphosphate + ?
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
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?
dimethylallyl diphosphate + 5-bromo-DL-tryptophan
diphosphate + 5-bromo-4-(3-methylbut-2-enyl)-DL-tryptophan
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0.2% of the yield with L-tryptophan
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?
dimethylallyl diphosphate + 5-fluoro-L-tryptophan
diphosphate + 5-fluoro-4-(3-methylbut-2-enyl)-L-tryptophan
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0.2% of the yield with L-tryptophan
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?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-hydroxy-L-tryptophan
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?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
?
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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)
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?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 5-methoxy-4-(3-methylbut-2-enyl)-DL-tryptophan
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0.6% of the yield with L-tryptophan
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?
dimethylallyl diphosphate + 5-methyl-D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-D-tryptophan
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0.5% of the activity with L-tryptophan
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?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
?
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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)
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?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
dimethylallyl diphosphate + 5-methyl-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan
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?
dimethylallyl diphosphate + 5-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-4-(3-methylbut-2-enyl)-DL-tryptophan
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0.2% of the yield with L-tryptophan
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?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
?
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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)
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?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
dimethylallyl diphosphate + 6-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-L-tryptophan
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan + ?
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16.3% of the yield with L-tryptophan
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?
dimethylallyl diphosphate + 7-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-7-methyl-L-tryptophan
dimethylallyl diphosphate + alpha-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-alpha-methyl-DL-tryptophan
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?
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
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?
dimethylallyl diphosphate + beta-homo-L-tryptophan
?
51.5% of the activity with L-Trp
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?
dimethylallyl diphosphate + bishomotryptophan
diphosphate + bis[4-(3-methylbut-2-enyl)]-L-homotryptophan
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2% of the activity with tryptophan
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?
dimethylallyl diphosphate + cyclo-D-Trp-L-Tyr
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
cyclo-D-Trp-L-Tyr is converted by wild-type enzyme (FgaPT2) with a product yield of 10.0%. I80F demonstrates similar catalytic ability as the wild-type enzyme
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?
dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Pro
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-
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?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
dimethylallyl diphosphate + cyclo-L-Trp-L-Phe
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Phe
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-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
dimethylallyl diphosphate + cyclo-L-Trp-L-Tyr
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Tyr
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-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-glycine
diphosphate + cyclo-L-4-dimethylallyltryptophan-glycine
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-
-
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?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-leucine
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-leucine
-
-
-
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?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-proline
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-proline
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-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-tryptophan
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-tryptophan
-
-
-
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?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-tyrosine
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-tyrosine
-
-
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-4-(3-methylbut-2-enyl)-tryptophan
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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
-
-
-
?
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
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 4-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
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
-
-
-
?
dimethylallyl diphosphate + indole-3-acetic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-acetic acid
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-butyric acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-butyric acid
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-propionic acid
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-pyruvic acid
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-beta-homotryptophan
-
51.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-homotryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-m-tyrosine
diphosphate + 4-(3-methylbut-2-enyl)-L-m-tyrosine + 6-(3-methylbut-2-enyl)-L-m-tyrosine
C-4 and C-6 prenylation, proposed reaction mechanism, overview
-
-
?
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
diphosphate + 4-(3-methylbut-2-enyl)-L-Trp
the enzyme (FgaPT2) from Aspergillus fumigatus catalyzes a Friedel-Crafts alkylation at C-4 of L-Trp
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-dimethylallyl-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(3-methylbut-2-enyl)-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan hydroxamate
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan hydroxamate
-
22.4% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
dimethylallyl diphosphate + L-Tyr
diphosphate + 3-(3-methylbut-2-enyl)-L-Tyr
C-3 prenylation
3-dimethylallyl-L-tyrosine
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-DL-4-(gamma,gamma-dimethylallyl)tryptophan
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + N-methyl-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-N-methyl-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-4-(gamma,gamma-dimethylallyl)tryptophan
dimethylallyl diphosphate + serotonin
diphosphate + 4-(3-methylbut-2-enyl)-serotonin
-
-
-
-
?
dimethylallyl diphosphate + tryptamin
diphosphate + 4-(3-methylbut-2-enyl)-tryptamin
-
-
-
-
?
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)
-
-
?
dimethylallyl S-thiolodiphosphate + L-tryptophan
?
-
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
-
-
-
-
?
geranyl diphosphate + L-tryptophan
diphosphate + ?
very low activity, 0.7% of the activity with dimethylallyl diphosphate
-
-
ir
isopentenyl diphosphate + L-tryptophan
diphosphate + ?
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
-
very low activity
-
-
?
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 + 1-methyl-L-tryptophan
diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-L-tryptophan
-
0.4% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-L-tryptophan
-
3.2% of the yield with L-tryptophan
-
?
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 + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
21.0% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
21.0% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
21.0% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
-
17.0% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-DL-tryptophan
11.6% of the activity with L-tryptophan
-
-
ir
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
8.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
8.1% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
8.1% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
16.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan
-
7.4% of the activity with L-tryptophan
-
-
?
dimethylallyl diphosphate + 5-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-L-tryptophan
-
7.4% of the activity with L-tryptophan
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
6.8% of the activity with L-tryptophan
-
-
ir
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
15.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
15.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
15.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
27.0% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-L-tryptophan
-
9.8% of the activity with tryptophan
-
-
?
dimethylallyl diphosphate + 6-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-6-methyl-L-tryptophan
-
9.8% of the activity with tryptophan
-
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
16.3% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
-
16.3% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + 7-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-7-methyl-L-tryptophan
-
40.5% of the activity with tryptophan
-
-
?
dimethylallyl diphosphate + 7-methyltryptophan
diphosphate + 4-(3-methylbut-2-enyl)-7-methyl-L-tryptophan
-
40.5% of the activity with tryptophan
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-Gly
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Leu
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Leu
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Pro
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-L-Trp
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-L-Trp
-
-
-
?
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
-
-
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
1.8% of the activity with L-tryptophan
-
-
ir
dimethylallyl diphosphate + D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
9.7% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-D-tryptophan
-
9.7% of the activity with L-Trp
-
-
?
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 + DL-indole-3-lactic acid
?
10.5% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 4-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
-
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 4-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
-
10.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid
?
32.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + indole-3-propionic acid
?
-
32.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-propionic acid
-
-
-
-
?
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-propionic acid
-
32.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-pyruvic acid
-
-
-
-
?
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 4-(3-methylbut-2-enyl)-indole-3-pyruvic acid
-
29.4% of the yield with L-tryptophan
-
?
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-abrine
?
58.0% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + L-abrine
?
-
58.0% of the activity with L-Trp
-
-
?
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-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 + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
r
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
best substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
first key step in ergot alkaloid biosynthesis providing the pharmaceutically relevant compounds lysergic acid, ergotamine, fumigaclavine A-C, festuclavine, and elymoclavine
-
-
ir
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
enzyme shows high substrate specificity for dimethylallyl diphosphate and L-tryptophan
-
-
ir
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan