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2.5.1.80: 7-dimethylallyltryptophan synthase

This is an abbreviated version!
For detailed information about 7-dimethylallyltryptophan synthase, go to the full flat file.

Word Map on EC 2.5.1.80

Reaction

dimethylallyl diphosphate
+
L-tryptophan
=
diphosphate
 +
7-(3-methylbut-2-enyl)-L-tryptophan

Synonyms

7-dimethylallyl tryptophan synthase, 7-dimethylallyltryptophan synthase, 7-DMATS, 7-DMATSNeo, ANI_1_660114, CAK41583, dimethylallyltryptophan synthase, tryptophan C7-prenyltransferase

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.80 7-dimethylallyltryptophan synthase

Substrates Products

Substrates Products on EC 2.5.1.80 - 7-dimethylallyltryptophan synthase

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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-(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 + 1,6-dihydroxynaphthalene
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,6-diol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 1,7-dihydroxynaphthalene
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalene-1,7-diol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 1-methyl-DL-tryptophan
diphosphate + 1-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 1-methyl-L-tryptophan
diphosphate + 1-methyl-7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
35.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 1-naphthol
diphosphate + 4-(3-methylbut-2-en-1-yl)naphthalen-1-ol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 11-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: 33.5% (FgaPT2 followed by 7-DMATS), 4.8% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 11-methyl-DL-tryptophan
diphosphate + 11-methyl-DL-7-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
-
19.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 2,6-dihydroxynaphthalene
diphosphate + 1-(3-methylbut-2-en-1-yl)naphthalene-2,6-diol
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 2,7-dihydroxynaphthalene
diphosphate + 1-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol + 3-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol + 7-[(3-methylbut-2-en-1-yl)oxy]naphthalen-2-ol + 1,6-bis(3-methylbut-2-en-1-yl)naphthalene-2,7-diol
show the reaction diagram
-
-
1-(3-methylbut-2-en-1-yl)naphthalene-2,7-diol is the major product
-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-(3-methylbut-2-enyl)-L-tyrosine
show the reaction diagram
C-4 prenylation
-
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-amino-3-(3-methylbut-2-enyl)-L-phenylalanine
show the reaction diagram
C-4 prenylation
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 4-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-4-methyl-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 5-bromo-DL-tryptophan
diphosphate + 5-bromo-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
7.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-bromo-L-tryptophan
diphosphate + 5-bromo-4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
low activity
-
-
?
dimethylallyl diphosphate + 5-fluoro-L-tryptophan
diphosphate + 5-fluoro-7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
10.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-4-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 5-hydroxy-L-tryptophan
diphosphate + 5-hydroxy-7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
-
26.7% of the yield with L-tryptophan
-
?
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-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
13.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methoxy-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methoxy-DL-tryptophan
show the reaction diagram
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 + 5-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 5-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
74.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-5-methyl-DL-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
-
-
-
?
dimethylallyl diphosphate + 6-fluoro-DL-tryptophan
diphosphate + 6-fluoro-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
33.7% 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 + 6-methyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
low activity
-
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 6-methyl-7-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
19.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + 6-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-6-methyl-DL-tryptophan
show the reaction diagram
dimethylallyl diphosphate + 7-methyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-DL-tryptophan + ?
show the reaction diagram
-
0.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + apigenin
diphosphate + ?
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + ardeemin fumiquinazoline
diphosphate + (1S,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4R)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
dimethylallyl diphosphate + beta-homo-L-tryptophan
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + biochanin A
diphosphate + gancaonin A
show the reaction diagram
-
15.9% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + cyclo-L-Trp-Gly
diphosphate + cyclo-L-7-(3-methylbut-2-enyl)-Trp-Gly
show the reaction diagram
-
1.8% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + D-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: 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
show the reaction diagram
low activity
-
-
?
dimethylallyl diphosphate + D-tryptophan
diphosphate + D-7-(3-methylbut-2-enyl)-tryptophan
show the reaction diagram
dimethylallyl diphosphate + dia,ent-ardeemin fumiquinazoline
diphosphate + (1R,4R)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1R,4R)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
dimethylallyl diphosphate + dia-ardeemin fumiquinazoline
diphosphate + (1S,4S)-4-methyl-1-[[6-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione + (1S,4S)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + DL-indole-3-lactic acid
?
show the reaction diagram
dimethylallyl diphosphate + DL-indole-3-lactic acid
diphosphate + 7-(3-methylbut-2-enyl)-DL-indole-3-lactic acid
show the reaction diagram
-
4.3% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + ent-ardeemin fumiquinazoline
diphosphate + (1R,4S)-4-methyl-1-[[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl]-2H-pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + eriodictyol
diphosphate + 6-(3-methylbut-2-enyl)eriodictyol
show the reaction diagram
-
19.0% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + genistein
diphosphate + wighteone
show the reaction diagram
-
10.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + hesperetin
diphosphate + sigmoidin B
show the reaction diagram
-
1.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + indole-3-acetic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-acetic acid
show the reaction diagram
-
10.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-butyric acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-butyric acid
show the reaction diagram
-
9.1% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-propionic acid
?
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + indole-3-propionic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-propionic acid
show the reaction diagram
-
8.5% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + indole-3-pyruvic acid
diphosphate + 7-(3-methylbut-2-enyl)-indole-3-pyruvic acid
show the reaction diagram
-
4.8% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-abrine
?
show the reaction diagram
dimethylallyl diphosphate + L-abrine
diphosphate + ?
show the reaction diagram
dimethylallyl diphosphate + L-beta-homotryptophan
?
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: 31.5% (FgaPT2 followed by 7-DMATS), 6.6% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + L-beta-homotryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-beta-homotryptophan
show the reaction diagram
dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 4-(3-methylbut-2-enyl)-L-o-tyrosine
show the reaction diagram
C-4 prenylation
4-dimethylallyl-L-o-tyrosine
-
?
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-Trp-Gly
diphosphate + L-7-(3-methylbut-2-enyl)-Trp-Gly
show the reaction diagram
-
10.9% of the activity with L-tryptophan
-
?
dimethylallyl diphosphate + L-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: 89.7% (FgaPT2 followed by 7-DMATS), 20% (7-DMATS followed by FgaPT2)
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan
diphosphate + L-7-(3-methylbut-2-enyl)-tryptophan
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan hydroxamate
diphosphate + L-7-(gamma,gamma-dimethylallyl)tryptophan hydroxamate
show the reaction diagram
-
4.6% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + L-tryptophan methyl ester
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan methyl ester
show the reaction diagram
dimethylallyl diphosphate + L-tyrosine
diphosphate + 5-[(2E)-pent-2-en-1-yl]-L-tryptophan
show the reaction diagram
O-4 prenylation
-
-
?
dimethylallyl diphosphate + luteolin
diphosphate + ?
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-N-acetyl-DL-tryptophan
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-4-(3-methylbut-2-enyl)-DL-tryptophan
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + N-acetyl-DL-tryptophan
diphosphate + N-acetyl-DL-7-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
-
7.7% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + Nalpha-methyl-L-tryptophan
diphosphate + Nalpha-methyl-L-7-(gamma,gamma-dimethylallyl)tryptophan
show the reaction diagram
i.e. L-abrine
82.2% of the yield with L-tryptophan
-
?
dimethylallyl diphosphate + naringenin
diphosphate + 6-(3-methylbut-2-enyl)naringenin
show the reaction diagram
-
1.4% activity compared to substrate L-tryptophan
-
-
?
dimethylallyl diphosphate + phloretin
diphosphate + 6-dimethylallyl-5,7,9,1'-tetrahydroxydihydrochalcone
show the reaction diagram
-
17.4% activity compared to substrate L-tryptophan
-
-
?
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 + 7-(3-methylbut-2-enyl)-tryptamine
show the reaction diagram
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
?
-