2.5.1.34: 4-dimethylallyltryptophan synthase
This is an abbreviated version!
For detailed information about 4-dimethylallyltryptophan synthase, go to the full flat file.
Word Map on EC 2.5.1.34
-
2.5.1.34
-
prenyltransferases
-
indole
-
ergot
-
dmapp
-
tryptophan-containing
-
disaster
-
claviceps
-
o-prenyltransferase
-
o-prenylated
-
neosartorya
-
hydroxynaphthalenes
-
earthquake
-
friedel-crafts
-
anapt
-
c-prenylation
-
clavine
-
ftmpt1
-
synthesis
-
biotechnology
- 2.5.1.34
- prenyltransferases
- indole
-
ergot
-
dmapp
-
tryptophan-containing
-
disaster
- claviceps
-
o-prenyltransferase
-
o-prenylated
- neosartorya
-
hydroxynaphthalenes
-
earthquake
-
friedel-crafts
- anapt
-
c-prenylation
-
clavine
- ftmpt1
- synthesis
- biotechnology
Reaction
Synonyms
4-(gamma,gamma-dimethylallyl)tryptophan synthase, 4-dimethylallyltryptophan synthase, 4-DMATS, 7-dimethylallyltryptophan synthase, 7-DMATS, C4-prenyltransferase, dimethylallyl-tryptophan synthase, dimethylallylpyrophosphate:L-tryptophan dimethylallyltransferase, dimethylallylpyrophosphate:tryptophan dimethylallyl transferase, dimethylallylpyrophosphate:tryptophan dimethylallyltransferase, dimethylallyltransferase, tryptophan, dimethylallyltryptophan synthase, dimethylallyltryptophan synthetase, DMAT synthase, DMAT synthetase, DMATS, DmaW, DmaW2, FgaPT2, IfgA, MaPT, Proq05g069320, tryptophan C4-prenyltransferase, tryptophan C4-prenyltransferase FgaPT2, tryptophan C4-PT
ECTree
2.5.1.34 4-dimethylallyltryptophan synthaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 2.5.1.34 - 4-dimethylallyltryptophan synthase
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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
-
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
C-5 prenylation
-
-
?
4-dimethylallyl-indole-3-lactic acid
?
10.5% of the activity with L-Trp
-
-
?
4-dimethylallyl-indole-3-pyruvic acid
?
29.4% of the activity with L-Trp
-
-
?
benzyl diphosphate + L-tryptophan
diphosphate + 5-benzyl-L-tryptophan
C-5 prenylation
-
-
?
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
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-DL-4-(gamma,gamma-dimethylallyl)tryptophan
-
1.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 4-amino-L-Phe
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-Phe
C-3 prenylation
-
-
?
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
-
-
?
dimethylallyl diphosphate + 4-amino-L-tryptophan
diphosphate + 4-amino-5-(3-methylbut-2-en-1-yl)-L-tryptophan
-
-
-
?
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
-
?
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
-
-
-
?
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
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-DL-tryptophan + ?
-
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
-
-
-
?
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
-
?
dimethylallyl diphosphate + 5-bromo-DL-tryptophan
diphosphate + 5-bromo-4-(3-methylbut-2-enyl)-DL-tryptophan
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-fluoro-L-tryptophan
diphosphate + 5-fluoro-4-(3-methylbut-2-enyl)-L-tryptophan
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-hydroxy-L-tryptophan
-
-
-
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
?
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 10.3% (FgaPT2 followed by 7-DMATS), 3.5% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 5-methoxy-4-(3-methylbut-2-enyl)-DL-tryptophan
-
0.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-D-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-5-methyl-D-tryptophan
-
0.5% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
?
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 24.3% (FgaPT2 followed by 7-DMATS), 0.9% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 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
-
-
-
?
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
-
0.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
?
-
tandem incubation of dimethylallyltryptophan synthases FgaPT2 and 7-DMATS (EC 2.5.1.34 and EC 2.5.1.80) leads to the production of diprenylated indole derivatives. Yield of diprenylated product: 2.6% (FgaPT2 followed by 7-DMATS), 1.5% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 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 + ?
-
16.3% of the yield with L-tryptophan
-
?
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
-
-
-
-
?
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
-
-
-
?
dimethylallyl diphosphate + beta-homo-L-tryptophan
?
51.5% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + bishomotryptophan
diphosphate + bis[4-(3-methylbut-2-enyl)]-L-homotryptophan
-
2% of the activity with tryptophan
-
-
?
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
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-D-Pro
diphosphate + 4-(3-methylbut-2-enyl)-cyclo-L-Trp-D-Pro
-
-
-
?
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
-
-
-
?
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
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-glycine
diphosphate + cyclo-L-4-dimethylallyltryptophan-glycine
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-leucine
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-leucine
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-proline
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-proline
-
-
-
-
?
dimethylallyl diphosphate + cyclo-L-tryptophan-L-tryptophan
diphosphate + cyclo-L-4-dimethylallyltryptophan-L-tryptophan
-
-
-
-
?
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
-
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
-
cleavage of the C-O bond in DMAPP is reversible
-
-
r
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
dimethylallyl diphosphate is the preferred substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
-
L-tryptophan is the preferred substrate
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
C-4 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
preferred enzyme of the wild-type enzyme
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
the enzyme prenylates the non-nucleophilic C-4 position of the indole ring in free tryptophan
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
the enzyme is involved in the biosynthesis of the ergot alkaloids fumigaclavines
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
the enzyme is involved in the biosynthesis of the ergot alkaloids fumigaclavines
-
-
?
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
dimethylallyltryptophan synthase catalyzes both normal and reverse prenylation at C3 of the indole ring and normal prenylation of N1
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan
L-tryptophan is the preferred substrate
-
-
?
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
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
first pathway-specific enzyme of ergot alkaloid biosynthesis
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
first pathway-specific enzyme of ergot alkaloid biosynthesis
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
first pathway-specific enzyme of ergot alkaloid biosynthesis
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-4-(gamma,gamma-dimethylallyl)tryptophan
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
-
-
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
-
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
-
7.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 4-(3-methylbut-2-enyl)-L-tryptophan methyl ester
7.2% of the activity with L-Trp
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
C-3 prenylation
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
low activity with the wild-type enzyme, higher activity with the enzyme mutant K174F
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 3-(3-methylbut-2-enyl)-L-tyrosine
low activity with the wild-type enzyme, higher activity with the enzyme mutantsM328L and Y398F
-
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-4-(gamma,gamma-dimethylallyl)tryptophan
i.e. L-abrine
58.0% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-4-(gamma,gamma-dimethylallyl)tryptophan
i.e. L-abrine
24.9% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + tryptamine
diphosphate + 4-(3-methylbut-2-enyl)-tryptamine
-
4.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + tryptamine
diphosphate + 4-(3-methylbut-2-enyl)-tryptamine
4.6% of the activity with L-Trp
-
-
?
additional information
?
-
no activity with 4-hydroxyphenylpyruvate, umbelliferone, or 4-hydroxybenzoate the enzyme contains no prenyl diphosphate binding site (N/D)DXXD
-
-
?
additional information
?
-
-
no activity with 4-hydroxyphenylpyruvate, umbelliferone, or 4-hydroxybenzoate the enzyme contains no prenyl diphosphate binding site (N/D)DXXD
-
-
?
additional information
?
-
-
halogenated derivatives of tryptophan are not accepted as substrates
-
-
?
additional information
?
-
-
FgaPT2 catalyzes prenylation of L-tryptophan at C-4 of the indole ring and function as 4-DMATS
-
-
?
additional information
?
-
-
the dimethylallyltryptophan synthase catalyzes the normal prenylation of Trp at C-4. The Lys174Ala mutant produces a hexahydropyrroloindole alkaloid that is reverse-prenylated at C-3 as its major product, by a mechanism that involves an initial reverse-prenylation at C-3, followed by a Cope rearrangement and rearomatization
-
-
?
additional information
?
-
-
the enzyme catalyzes a Friedel-Crafts alkylation with high flexibility for aromatic substrates, but shows high specificity for dimethylallyl diphosphate. At least one methyl group in DMAPP can be deleted or shifted to the delta-position. For acceptance by some DMATS enzymes, however, a double bond must be situated at the beta-position. The alkylation position of an analogue can differ from that of dimethylallyl diphosphate. No activity with 3-methylbutanyl-diphosphate and 4-methyl-3-pentenyl-diphosphate. Product identification with NMR spectroscopy
-
-
?
additional information
?
-
HR-ESI-MS and NMR product analysis
-
-
?
additional information
?
-
no or poor activity with 1-methyl-L-tryptophan, 4-methyl-DL-tryptophan, 6-fluoro-DL-tryptophan, 5-methoxy-L-tryptophan, idole-3-acetic acid, N-acetyl-DL-tryptophan, and cyclo-L-Trp-Gly, substrate specificity, docking study and molecular modelling, overview
-
-
?
additional information
?
-
-
no or poor activity with 1-methyl-L-tryptophan, 4-methyl-DL-tryptophan, 6-fluoro-DL-tryptophan, 5-methoxy-L-tryptophan, idole-3-acetic acid, N-acetyl-DL-tryptophan, and cyclo-L-Trp-Gly, substrate specificity, docking study and molecular modelling, overview
-
-
?
additional information
?
-
no or poor activity with N-acetyl-DL-Trp, 5-bromo-DL-Trp, 4-methyl-DL-Trp, 1-methyl-DL-Trp, and 6-fluoro-DL-Trp. The tryptophan prenyltransferase FgaPT2 takes L-tyrosine and 4-amino-L-phenylalanine as substrates as well and produces the unique C3-prenylated tyrosine or 4-amino-L-phenylalanine, cf. EC 2.5.1.122, no activity with D-Tyr, 3-fluoro-DL-Tyr, 3-iodo-L-Tyr, and alpha-methyl-L-Tyr. FgaPT2 also catalyzes regiospecific prenylations of indolocarbazoles at the para-position of the indole N-atom. In the presence of methylallyl diphosphate, MAPP, a mixture of C4- and C5-alkylated tryptophan is observed for FgaPT2 reaction,t FgaPT2 even uses the more space-demanding substrate benzyl diphosphate as donor and produces regiospecifically C5-benzylated tryptophan and eight derivatives thereof, overview
-
-
?
additional information
?
-
the enzyme catalyzes the C-4 prenylation of L-tryptophan, and also the C-3 prenylation of L-tyrosine, cf. EC 2.5.1.122. Single mutation on the key amino acid switches the tryptophan C4 prenyltransferase to a tyrosine C3-prenylating enzyme, active sites and proposed reaction model of FgaPT2 with substrates L-Tyr and 4-amino-L-phenylalanine, overview
-
-
?
additional information
?
-
-
the enzyme catalyzes the C-4 prenylation of L-tryptophan, and also the C-3 prenylation of L-tyrosine, cf. EC 2.5.1.122. Single mutation on the key amino acid switches the tryptophan C4 prenyltransferase to a tyrosine C3-prenylating enzyme, active sites and proposed reaction model of FgaPT2 with substrates L-Tyr and 4-amino-L-phenylalanine, overview
-
-
?
additional information
?
-
-
DmaW catalyzes prenylation of L-tryptophan at C-4 of the indole ring and function as 4-DMATS
-
-
?
additional information
?
-
-
4-DMATS catalyzes normal or reverse prenylation of tryptophan and C4-substituted analogues at five different sites on the indole ring, N1, C3, C4, C5, and C7, depending on the substituent
-
-
?
additional information
?
-
4-DMATS catalyzes normal or reverse prenylation of tryptophan and C4-substituted analogues at five different sites on the indole ring, N1, C3, C4, C5, and C7, depending on the substituent
-
-
?
additional information
?
-
-
normal prenylation at C-4 of tryptophan is catalyzed by dimethylallyltryptophan synthase, the enzyme forms a C-C bond at the least nucleophilic position (C-4) of the indole core, instead of the highly nucleophilic positions C-2 and C-3
-
-
?
additional information
?
-
-
4-DMATS catalyzes normal prenylation at C4 of L-tryptophan. When C4 is blocked, 4-DMATS catalyzes alkylation at all of the activated positions, except weakly activated C6, depending on the electron-donating properties of the blocking substituent. In addition, both normal and reverse prenylation is seen at C3 for 4-methyltryptophan. The high regioselectivity for C4 alkylation with the normal substrates suggests that binding and catalysis of a single conformation has been optimized for synthesis of 4-dimethylallyltryptophan, but when alkylation at C4 is blocked, alkylation from other conformations becomes competitive
-
-
?
additional information
?
-
4-DMATS catalyzes normal prenylation at C4 of L-tryptophan. When C4 is blocked, 4-DMATS catalyzes alkylation at all of the activated positions, except weakly activated C6, depending on the electron-donating properties of the blocking substituent. In addition, both normal and reverse prenylation is seen at C3 for 4-methyltryptophan. The high regioselectivity for C4 alkylation with the normal substrates suggests that binding and catalysis of a single conformation has been optimized for synthesis of 4-dimethylallyltryptophan, but when alkylation at C4 is blocked, alkylation from other conformations becomes competitive
-
-
?
additional information
?
-
-
4-methyltryptophan is an alternate substrate for 4-DMATS
-
-
?
additional information
?
-
4-methyltryptophan is an alternate substrate for 4-DMATS
-
-
?
additional information
?
-
-
MaPT catalyzes prenylation of L-tryptophan at C-4 of the indole ring and function as 4-DMATS
-
-
?
