2.5.1.122: 4-O-dimethylallyl-L-tyrosine synthase
This is an abbreviated version!
For detailed information about 4-O-dimethylallyl-L-tyrosine synthase, go to the full flat file.
Word Map on EC 2.5.1.122
-
2.5.1.122
-
prenyltransferases
-
maculans
-
leptosphaeria
-
prenylation
-
indole
-
c-prenylations
-
dimethylallyltryptophan
-
dmapp
-
thereof
-
regiospecific
-
7-dmats
-
l-tryptophan
-
unnatural
-
phytotoxin
-
synthesis
-
niger
- 2.5.1.122
- prenyltransferases
- maculans
-
leptosphaeria
-
prenylation
- indole
-
c-prenylations
- dimethylallyltryptophan
-
dmapp
-
thereof
-
regiospecific
- 7-dmats
- l-tryptophan
-
unnatural
-
phytotoxin
- synthesis
- niger
Reaction
Synonyms
ANI_1_660114, CAK41583, SirD, tyrosine O-prenyltransferase, tyrosine-O-prenyltransferase, TyrPT
ECTree
2.5.1.122 4-O-dimethylallyl-L-tyrosine synthaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 2.5.1.122 - 4-O-dimethylallyl-L-tyrosine 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
(2E)-2-methylpenta-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E)-2-methylpenta-2,4-dien-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-3-(2-methoxyphenyl)prop-2-en-1-yl trihydrogen diphosphate + L-tyrosine
O-[(2E)-3-(2-methoxyphenyl)prop-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-3-methylpent-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-3-methylpent-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-3-phenylbut-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-3-phenylbut-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-3-phenylprop-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-3-phenylprop-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-5-methylhexa-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E)-5-methylhexa-2,4-dien-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-but-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-but-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E)-penta-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E)-penta-2,4-dien-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E,4E)-2-methylhexa-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E,4E)-2-methylhexa-2,4-dien-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2E,4E)-5-phenylpenta-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E,4E)-5-phenylpenta-2,4-dien-1-yl]-L-tyrosine + diphosphate
-
-
-
?
(2Z)-3-chlorobut-2-en-1-yl diphosphate + L-tyrosine
O-[(2Z)-3-chlorobut-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
2-cyclohexylideneethyl diphosphate + L-tyrosine
O-[2-cyclohexylideneethyl]-L-tyrosine + diphosphate
-
-
-
?
2-methylprop-2-en-1-yl diphosphate + L-tyrosine
O-[2-methylprop-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
2-oxopropyl diphosphate + L-tyrosine
O-[2-oxopropyl]-L-tyrosine + diphosphate
-
-
-
?
2-pentenyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine
2-pentenyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(2-pentenylamino)-L-phenylalanine
2-pentenyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine
3,3-diphenylprop-2-en-1-yl diphosphate + L-tyrosine
O-[3,3-diphenylprop-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
3-ethylpent-2-en-1-yl diphosphate + L-tyrosine
O-[3-ethylpent-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
benzyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(benzylamino)-L-phenylalanine
cyanomethyl diphosphate + L-tyrosine
O-[cyanomethyl]-L-tyrosine + diphosphate
-
-
-
?
cyclohex-1-en-1-ylmethyl diphosphate + L-tyrosine
O-[cyclohex-1-en-1-ylmethyl]-L-tyrosine + diphosphate
-
-
-
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
?
98% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + ?
-
-
-
?
dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine
diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine
dimethylallyl diphosphate + 3-amino-L-tyrosine
diphosphate + 3-amino-4-O-dimethylallyl-L-tyrosine
-
SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Amino-L-tyrosine is prenylated with 108% of the activity compared to L-tyrosine
-
-
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
?
53% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 4-O-dimethylallyl-3-fluoro-DL-tyrosine
-
SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Iodo-L-tyrosine is prenylated with 53.6% of the activity compared to L-tyrosine
-
-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 4-O-dimethylallyl-3-iodo-L-tyrosine
-
SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Iodo-L-tyrosine is prenylated with 27.3% of the activity compared to L-tyrosine
-
-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + ?
-
-
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
?
23% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(dimethylallylamino)-L-phenylalanine
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-dimethylallylamino-L-phenylalanine
prenylation at 4-O- or N-atom
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
?
13% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-dimethylallyl-4-methyl-L-tryptophan
41% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-dimethylally-5-methyl-L-tryptophan
10% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
?
98% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine
dimethylallyl diphosphate + D-tyrosine
?
33% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + L-3,4-dihydroxyphenylalanine
?
16.6% of the activity, compared to L-tyrosine. It is expected that the prenylation takes place at the 4-hydroxyl group. The structure of the product is not determined
-
-
?
dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine
-
C-5 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 1-(2-methylbut-3-en-2-yl)-L-tryptophan
reverse prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
C-7 prenylation
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyltryptophan
catalytic efficiency for L-tryptophan is 6% compared to catalytic efficiency for L-tyrosine
-
-
?
methylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(methylallylamino)-L-phenylalanine
prop-2-en-1-yl diphosphate + L-tyrosine
O-[prop-2-en-1-yl]-L-tyrosine + diphosphate
-
-
-
?
prop-2-yn-1-yl diphosphate + L-tyrosine
O-[prop-2-yn-1-yl]-L-tyrosine + diphosphate
-
-
-
?
2-pentenyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine
-
-
43.9% conversion
-
?
2-pentenyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine
-
20.5% conversion
-
?
2-pentenyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(2-pentenylamino)-L-phenylalanine
-
-
46.4% conversion
-
?
2-pentenyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(2-pentenylamino)-L-phenylalanine
-
42.6% conversion
-
?
2-pentenyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine
-
-
10.3% conversion
-
?
2-pentenyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine
-
33.5% conversion
-
?
2-pentenyl diphosphate + L-tyrosine
diphosphate + 4-O-(2-pentenyl)-L-tyrosine
-
-
56.6% conversion
-
?
2-pentenyl diphosphate + L-tyrosine
diphosphate + 4-O-(2-pentenyl)-L-tyrosine
-
44.3% conversion
-
?
benzyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(benzylamino)-L-phenylalanine
-
-
67.2% conversion
-
?
benzyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(benzylamino)-L-phenylalanine
-
54.6% conversion
-
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine
-
-
100% conversion
-
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine
-
88.2% conversion
-
?
dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine
diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine
-
-
20.6% conversion
-
?
dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine
diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine
-
53.3% conversion
-
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine
-
-
50.1% conversion
-
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine
-
66.5% conversion
-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine
-
-
100% conversion
-
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine
-
100% conversion
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(dimethylallylamino)-L-phenylalanine
-
-
78.1% conversion
-
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(dimethylallylamino)-L-phenylalanine
-
66.1% conversion
-
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine
-
-
98.3% conversion
-
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine
-
89.4% conversion
-
?
dimethylallyl diphosphate + D-tyrosine
diphosphate + 4-O-dimethylallyl-D-tyrosine
-
-
-
?
dimethylallyl diphosphate + D-tyrosine
diphosphate + 4-O-dimethylallyl-D-tyrosine
-
-
59.5% conversion
-
?
dimethylallyl diphosphate + D-tyrosine
diphosphate + 4-O-dimethylallyl-D-tyrosine
-
57.6% conversion
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyl-L-tryptophan
33% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyl-L-tryptophan
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
-
89.1% conversion
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
98% activity compared to 3-iodo-L-tyrosine
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
O-4 prenylation
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
-
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
99.3% conversion
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
first committed step in the biosynthesis of the phytotoxin sirodesmin PL
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
the enzyme is involved in biosynthesis of sirodesmin PL
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
the enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
no activity with cyclo-L-Tyr-L-Ser, L-Phe, 4-hydroxybenzoate or 4-coumarate
-
-
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives
-
-
?
methylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(methylallylamino)-L-phenylalanine
-
-
57.7% conversion
-
?
methylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(methylallylamino)-L-phenylalanine
-
34.8% conversion
-
?
methylallyl diphosphate + L-tyrosine
diphosphate + 4-O-methylallyl-L-tyrosine
-
-
21.2% conversion
-
?
methylallyl diphosphate + L-tyrosine
diphosphate + 4-O-methylallyl-L-tyrosine
-
28% conversion
-
?
additional information
?
-
-
the enzyme catalyzes C7-prenylation of the indole ring, EC 2.5.1.80, but also accepts L-tyrosine as substrate and converts it to an O-prenylated derivative, EC 2.5.1.122. 7-DMATS is able to take L-tyrosine and two derivatives thereof as substrates and catalyzed the same O- or N-prenylation
-
-
?
additional information
?
-
-
HR-ESI-MS and NMR product analysis. No activity with L-m-tyrosine
-
-
?
additional information
?
-
-
in presence of unnatural dimethylallyl diphosphate analogs such as methylallyl, 2-pentenyl and benzyl diphosphate for alkylation, or benzylation of the indole ring enzyme catalyzes the regiospecific O- or N-alkylation or benzylation at position C4 of the aromatic ring
-
-
?
additional information
?
-
-
the enzyme shows a wider substrate spectrum compared to tyrosine prenyltransferase SirD. It catalyzes O-prenylation of L-tyrosine, EC 2.5.1.122, and also accepts 4-amino-L-phenylalanine for an N-prenylation and L-tryptophan for a C7-prenylation, EC 2.5.1.80. It is also active with 4-amino-L-phenylalanine as well as 4- and 5-methyl-DL-tryptophan. HRMS analysis of the enzyme products, overview. 3,5-dibromo-L-tyrosine is a poor substrate
-
-
?
additional information
?
-
the enzyme shows a wider substrate spectrum compared to tyrosine prenyltransferase SirD. It catalyzes O-prenylation of L-tyrosine, EC 2.5.1.122, and also accepts 4-amino-L-phenylalanine for an N-prenylation and L-tryptophan for a C7-prenylation, EC 2.5.1.80. It is also active with 4-amino-L-phenylalanine as well as 4- and 5-methyl-DL-tryptophan. HRMS analysis of the enzyme products, overview. 3,5-dibromo-L-tyrosine is a poor substrate
-
-
?
additional information
?
-
-
SirD also catalyses the C-prenylation of L-Trp derivatives, in addition to the O-prenylation
-
-
?
additional information
?
-
SirD also prenylates L-Trp, resulting in the formation of 7-dimethylallyltryptophan. SirD catalyses the C-prenylation of L-Trp, in addition to the O-prenylation of L-Tyr, cf. EC 2.5.1.34
-
-
?
additional information
?
-
-
SirD also prenylates L-Trp, resulting in the formation of 7-dimethylallyltryptophan. SirD catalyses the C-prenylation of L-Trp, in addition to the O-prenylation of L-Tyr, cf. EC 2.5.1.34
-
-
?
additional information
?
-
the catalytic erfficiency with 4-mercapto-L-phenylalanine, 4-methoxy-L-tryptophan and 7-methyl-L-tryptophan is less than 1% of the reaction with L-tyrosine
-
-
?
additional information
?
-
-
the catalytic erfficiency with 4-mercapto-L-phenylalanine, 4-methoxy-L-tryptophan and 7-methyl-L-tryptophan is less than 1% of the reaction with L-tyrosine
-
-
?
additional information
?
-
-
no activity with 1-naphthol, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 3,5-dihydroxy-2-naphthoic acid, and 3,7-dihydroxy-2-naphthoic acid
-
-
?
additional information
?
-
in presence of unnatural dimethylallyl diphosphate analogs such as methylallyl, 2-pentenyl and benzyl diphosphate for alkylation, or benzylation of the indole ring enzyme catalyzes the regiospecific O- or N-alkylation or benzylation at position C4 of the aromatic ring
-
-
?
additional information
?
-
-
in presence of unnatural dimethylallyl diphosphate analogs such as methylallyl, 2-pentenyl and benzyl diphosphate for alkylation, or benzylation of the indole ring enzyme catalyzes the regiospecific O- or N-alkylation or benzylation at position C4 of the aromatic ring
-
-
?
