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Information on EC 2.5.1.122 - 4-O-dimethylallyl-L-tyrosine synthase
for references in articles please use BRENDA:EC2.5.1.122
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EC Tree 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)
2.5.1.122 4-O-dimethylallyl-L-tyrosine synthase
IUBMB Comments
The enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL by the phytopathogenic ascomycete Leptosphaeria maculans.
The enzyme appears in viruses and cellular organisms
- 2.5.1.122
- prenyltransferases
- maculans
-
leptosphaeria
-
prenylation
- indole
-
c-prenylations
- dimethylallyltryptophan
-
dmapp
-
thereof
-
regiospecific
- 7-dmats
- l-tryptophan
-
unnatural
-
phytotoxin
- synthesis
- niger
Reaction Schemes
show+
=
+
4-O-prenyl-L-tyrosine
Synonyms
tyrpt, tyrosine o-prenyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
dimethylallyl diphosphate:L-tyrosine 4-O-dimethylallyltransferase
-
-
-
-
SirD
tyrosine O-prenyltransferase
TyrPT
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
prenyl diphosphate + L-tyrosine = diphosphate + 4-O-prenyl-L-tyrosine
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SYSTEMATIC NAME
IUBMB Comments
prenyl-diphosphate:L-tyrosine 4-O-prenyltransferase
The enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL by the phytopathogenic ascomycete Leptosphaeria maculans.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
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
Substrates: -
Products: -
Products: -
?
(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
Substrates: -
Products: -
Products: -
?
(2E)-3-methylpent-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-3-methylpent-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
(2E)-3-phenylbut-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-3-phenylbut-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
(2E)-3-phenylprop-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-3-phenylprop-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
(2E)-5-methylhexa-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E)-5-methylhexa-2,4-dien-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
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(2E)-but-2-en-1-yl diphosphate + L-tyrosine
O-[(2E)-but-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
(2E)-penta-2,4-dien-1-yl diphosphate + L-tyrosine
O-[(2E)-penta-2,4-dien-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
(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
Substrates: -
Products: -
Products: -
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(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
Substrates: -
Products: -
Products: -
?
(2Z)-3-chlorobut-2-en-1-yl diphosphate + L-tyrosine
O-[(2Z)-3-chlorobut-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
2-cyclohexylideneethyl diphosphate + L-tyrosine
O-[2-cyclohexylideneethyl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
2-methylprop-2-en-1-yl diphosphate + L-tyrosine
O-[2-methylprop-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
2-oxopropyl diphosphate + L-tyrosine
O-[2-oxopropyl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
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
Substrates: -
Products: -
Products: -
?
3-ethylpent-2-en-1-yl diphosphate + L-tyrosine
O-[3-ethylpent-2-en-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
benzyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(benzylamino)-L-phenylalanine
cyanomethyl diphosphate + L-tyrosine
O-[cyanomethyl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
cyclohex-1-en-1-ylmethyl diphosphate + L-tyrosine
O-[cyclohex-1-en-1-ylmethyl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
?
Substrates: 98% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + ?
Substrates: -
Products: -
Products: -
?
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
-
Substrates: 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
Products: -
Products: -
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
?
Substrates: 53% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
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
-
Substrates: 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
Products: -
Products: -
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
?
Substrates: 100% activity
Products: -
Products: -
?
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
-
Substrates: 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
Products: -
Products: -
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dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + ?
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
?
Substrates: 23% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(dimethylallylamino)-L-phenylalanine
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-dimethylallylamino-L-phenylalanine
Substrates: prenylation at 4-O- or N-atom
Products: -
Products: -
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
?
Substrates: 13% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + 4-methyl-DL-tryptophan
diphosphate + 7-dimethylallyl-4-methyl-L-tryptophan
Substrates: 41% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + 5-methyl-DL-tryptophan
diphosphate + 7-dimethylally-5-methyl-L-tryptophan
Substrates: 10% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
?
Substrates: 98% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine
dimethylallyl diphosphate + D-tyrosine
?
Substrates: 33% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + L-3,4-dihydroxyphenylalanine
?
Substrates: 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
Products: -
Products: -
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dimethylallyl diphosphate + L-o-tyrosine
diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine
-
Substrates: C-5 prenylation
Products: -
Products: -
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 1-(2-methylbut-3-en-2-yl)-L-tryptophan
Substrates: reverse prenylation
Products: -
Products: -
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
Substrates: C-7 prenylation
Products: -
Products: -
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyltryptophan
Substrates: catalytic efficiency for L-tryptophan is 6% compared to catalytic efficiency for L-tyrosine
Products: -
Products: -
?
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
Substrates: -
Products: -
Products: -
?
prop-2-yn-1-yl diphosphate + L-tyrosine
O-[prop-2-yn-1-yl]-L-tyrosine + diphosphate
Substrates: -
Products: -
Products: -
?
2-pentenyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine
-
Substrates: -
Products: 43.9% conversion
Products: 43.9% conversion
?
2-pentenyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine
Substrates: -
Products: 20.5% conversion
Products: 20.5% conversion
?
2-pentenyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(2-pentenylamino)-L-phenylalanine
-
Substrates: -
Products: 46.4% conversion
Products: 46.4% conversion
?
2-pentenyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(2-pentenylamino)-L-phenylalanine
Substrates: -
Products: 42.6% conversion
Products: 42.6% conversion
?
2-pentenyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine
-
Substrates: -
Products: 10.3% conversion
Products: 10.3% conversion
?
2-pentenyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine
Substrates: -
Products: 33.5% conversion
Products: 33.5% conversion
?
2-pentenyl diphosphate + L-tyrosine
diphosphate + 4-O-(2-pentenyl)-L-tyrosine
-
Substrates: -
Products: 56.6% conversion
Products: 56.6% conversion
?
2-pentenyl diphosphate + L-tyrosine
diphosphate + 4-O-(2-pentenyl)-L-tyrosine
Substrates: -
Products: 44.3% conversion
Products: 44.3% conversion
?
benzyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(benzylamino)-L-phenylalanine
-
Substrates: -
Products: 67.2% conversion
Products: 67.2% conversion
?
benzyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(benzylamino)-L-phenylalanine
Substrates: -
Products: 54.6% conversion
Products: 54.6% conversion
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine
-
Substrates: -
Products: 100% conversion
Products: 100% conversion
?
dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine
diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine
Substrates: -
Products: 88.2% conversion
Products: 88.2% conversion
?
dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine
diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine
-
Substrates: -
Products: 20.6% conversion
Products: 20.6% conversion
?
dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine
diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine
Substrates: -
Products: 53.3% conversion
Products: 53.3% conversion
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine
-
Substrates: -
Products: 50.1% conversion
Products: 50.1% conversion
?
dimethylallyl diphosphate + 3-fluoro-DL-tyrosine
diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine
Substrates: -
Products: 66.5% conversion
Products: 66.5% conversion
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: 100% conversion
Products: 100% conversion
?
dimethylallyl diphosphate + 3-iodo-L-tyrosine
diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: 100% conversion
Products: 100% conversion
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(dimethylallylamino)-L-phenylalanine
-
Substrates: -
Products: 78.1% conversion
Products: 78.1% conversion
?
dimethylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(dimethylallylamino)-L-phenylalanine
Substrates: -
Products: 66.1% conversion
Products: 66.1% conversion
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: 98.3% conversion
Products: 98.3% conversion
?
dimethylallyl diphosphate + alpha-methyl-L-tyrosine
diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: 89.4% conversion
Products: 89.4% conversion
?
dimethylallyl diphosphate + D-tyrosine
diphosphate + 4-O-dimethylallyl-D-tyrosine
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + D-tyrosine
diphosphate + 4-O-dimethylallyl-D-tyrosine
-
Substrates: -
Products: 59.5% conversion
Products: 59.5% conversion
?
dimethylallyl diphosphate + D-tyrosine
diphosphate + 4-O-dimethylallyl-D-tyrosine
Substrates: -
Products: 57.6% conversion
Products: 57.6% conversion
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyl-L-tryptophan
Substrates: 33% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + L-tryptophan
diphosphate + 7-dimethylallyl-L-tryptophan
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: 98% activity compared to 3-iodo-L-tyrosine
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: O-4 prenylation
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: 89.1% conversion
Products: 89.1% conversion
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: the enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL
Products: -
Products: -
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dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: the enzyme is involved in biosynthesis of sirodesmin PL
Products: -
Products: -
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dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: first committed step in the biosynthesis of the phytotoxin sirodesmin PL
Products: -
Products: -
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dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: no activity with cyclo-L-Tyr-L-Ser, L-Phe, 4-hydroxybenzoate or 4-coumarate
Products: -
Products: -
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dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: 99.3% conversion
Products: 99.3% conversion
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: -
Products: -
?
methylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(methylallylamino)-L-phenylalanine
-
Substrates: -
Products: 57.7% conversion
Products: 57.7% conversion
?
methylallyl diphosphate + 4-amino-L-phenylalanine
diphosphate + 4-(methylallylamino)-L-phenylalanine
Substrates: -
Products: 34.8% conversion
Products: 34.8% conversion
?
methylallyl diphosphate + L-tyrosine
diphosphate + 4-O-methylallyl-L-tyrosine
-
Substrates: -
Products: 21.2% conversion
Products: 21.2% conversion
?
methylallyl diphosphate + L-tyrosine
diphosphate + 4-O-methylallyl-L-tyrosine
Substrates: -
Products: 28% conversion
Products: 28% conversion
?
additional information
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Substrates: 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
Products: -
Products: -
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additional information
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Substrates: 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
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Products: -
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additional information
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Substrates: 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
Products: -
Products: -
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additional information
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Substrates: 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
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additional information
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Substrates: HR-ESI-MS and NMR product analysis. No activity with L-m-tyrosine
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Products: -
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additional information
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Substrates: 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
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Products: -
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additional information
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Substrates: SirD also catalyses the C-prenylation of L-Trp derivatives, in addition to the O-prenylation
Products: -
Products: -
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additional information
?
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Substrates: 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
Products: -
Products: -
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additional information
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Substrates: 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
Products: -
Products: -
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additional information
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Substrates: 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
Products: -
Products: -
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: O-4 prenylation
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: the enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: the enzyme is involved in biosynthesis of sirodesmin PL
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: first committed step in the biosynthesis of the phytotoxin sirodesmin PL
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
-
Substrates: -
Products: -
Products: -
?
dimethylallyl diphosphate + L-tyrosine
diphosphate + 4-O-dimethylallyl-L-tyrosine
Substrates: -
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
Mg2+
additional information
Ca2+
5 mM, 1.4fold activation compared to activity without additives
additional information
-
addition of K+, Na+, Mg2+, Mn2+, Co2+, or EDTA to the reaction mixture does not change the enzyme activity significantly
additional information
addition of K+, Na+, Mg2+, Mn2+, Co2+, or EDTA to the reaction mixture does not change the enzyme activity significantly
additional information
-
no significant effects on enzyme activity by K+, Na+, Mg2+, Mn2+, Co2+, or EDTA
additional information
no significant effects on enzyme activity by K+, Na+, Mg2+, Mn2+, Co2+, or EDTA
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.17
(2E)-2-methylpenta-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.12
(2E,4Z)-2-methylhexa-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.22
2-pentenyl diphosphate
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.23
2-pentenyl diphosphate
-
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.75
benzyl diphosphate
cosubstrate 4-aminophenylalanine, pH 7.5, 37°C
0.23
dimethylallyl diphosphate
with L-tyrosine as cosubstrate, at pH 7.5 and 35°C
0.71
dimethylallyl diphosphate
with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37°C
0.029
methylallyl diphosphate
-
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.13
methylallyl diphosphate
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00367
(2E)-2-methylpenta-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.00167
(2E)-5-methylhexa-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.0123
(2E,4Z)-2-methylhexa-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.002
2-pentenyl diphosphate
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.003
2-pentenyl diphosphate
-
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.028
benzyl diphosphate
cosubstrate 4-aminophenylalanine, pH 7.5, 37°C
0.683
dimethylallyl diphosphate
with L-tyrosine as cosubstrate, at pH 7.5 and 35°C
0.69
dimethylallyl diphosphate
with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37°C
0.002
methylallyl diphosphate
-
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.003
methylallyl diphosphate
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0217
(2E)-2-methylpenta-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.0023
(2E)-5-methylhexa-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.1017
(2E,4Z)-2-methylhexa-2,4-dien-1-yl diphosphate
at pH 7.5 and 35°C
0.014
2-pentenyl diphosphate
-
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.098
2-pentenyl diphosphate
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.037
benzyl diphosphate
cosubstrate 4-aminophenylalanine, pH 7.5, 37°C
0.972
dimethylallyl diphosphate
with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37°C
2.97
dimethylallyl diphosphate
with L-tyrosine as cosubstrate, at pH 7.5 and 35°C
0.021
methylallyl diphosphate
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
0.069
methylallyl diphosphate
-
cosubstrate 4-hydroxyphenylalanine, pH 7.5, 37°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
physiological function
physiological function
the enzyme is involved in biosynthesis of the epidithiopiperazinedione toxin sirodesmin PL by the phytopathogenic ascomycete Leptosphaeria maculans
physiological function
-
the enzyme is involved in biosynthesis of sirodesmin PL
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). DMAT1_GIBF5
Gibberella fujikuroi (strain CBS 195.34 / IMI 58289 / NRRL A-6831)
419
0
47291
Swiss-Prot
Chloroplast (Reliability: 1)
A2R1N3_ASPNC
Aspergillus niger (strain ATCC MYA-4892 / CBS 513.88 / FGSC A1513)
465
0
52682
TrEMBL
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
52700
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 53500, recombinant His6-tagged enzyme, SDS-PAGE, x * 52700, about, sequence calculation
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged enzyme from Escherichia coli strain BL21 to near homogeneity by nickel affinity chromatography and desalting gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene An13g01840, DNA and amino acid sequence determination and analysis, overexpression of His6-tagged enzyme in Escherichia coli strain SoluBL21, subcloning in Escherichia coli strain XL1 BlueMRF'
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
the specific 4-O-prenylation of tyrosine derivatives by SirD could find usage for production of prenylated tyrosine derivatives by chemoenzymatic synthesis
synthesis
the broad alkyl donor specificity of SirD opens the door for the interrogation of the alkyl donor specificity of other prenyltransferases for potential utility as biocatalysts for differential alkylation applications
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yu, X.; Xie, X.; Li, S.M.
Substrate promiscuity of secondary metabolite enzymes: prenylation of hydroxynaphthalenes by fungal indole prenyltransferases
Appl. Microbiol. Biotechnol.
92
737-748
2011
Plenodomus lingam
brenda
Rudolf, J.D.; Poulter, C.D.
Tyrosine O-prenyltransferase SirD catalyzes S-, C-, and N-prenylations on tyrosine and tryptophan derivatives
ACS Chem. Biol.
8
2707-2714
2013
Plenodomus lingam (Q6Q874)
brenda
Zou, H.X.; Xie, X.; Zheng, X.D.; Li, S.M.
The tyrosine O-prenyltransferase SirD catalyzes O-, N-, and C-prenylations
Appl. Microbiol. Biotechnol.
89
1443-1451
2011
Plenodomus lingam
brenda
Kremer, A.; Li, S.M.
A tyrosine O-prenyltransferase catalyses the first pathway-specific step in the biosynthesis of sirodesmin PL
Microbiology
156
278-286
2010
Plenodomus lingam (Q6Q874)
brenda
Fan, A.; Chen, H.; Wu, R.; Xu, H.; Li, S.M.
A new member of the DMATS superfamily from Aspergillus niger catalyzes prenylations of both tyrosine and tryptophan derivatives
Appl. Microbiol. Biotechnol.
98
10119-10129
2014
Aspergillus niger, Aspergillus niger (A2R1N3)
brenda
Yu, H.; Liebhold, M.; Xie, X.; Li, S.M.
Tyrosine O-prenyltransferases TyrPT and SirD displaying similar behavior toward unnatural alkyl or benzyl diphosphate as their natural prenyl donor dimethylallyl diphosphate
Appl. Microbiol. Biotechnol.
99
7115-7124
2015
Aspergillus niger, Plenodomus lingam (Q6Q874)
brenda
Fan, A.; Zocher, G.; Stec, E.; Stehle, T.; Li, S.M.
Site-directed mutagenesis switching a dimethylallyl tryptophan synthase to a specific tyrosine C3-prenylating enzyme
J. Biol. Chem.
290
1364-1373
2015
Aspergillus fumigatus
brenda
Fan, A.; Xie, X.; Li, S.M.
Tryptophan prenyltransferases showing higher catalytic activities for Friedel-Crafts alkylation of o- and m-tyrosines than tyrosine prenyltransferases
Org. Biomol. Chem.
13
7551-7557
2015
Aspergillus niger
brenda
Bandari, C.; Scull, E.M.; Masterson, J.M.; Tran, R.H.Q.; Foster, S.B.; Nicholas, K.M.; Singh, S.
Determination of alkyl-donor promiscuity of tyrosine-O-prenyltransferase SirD from Leptosphaeria maculans
ChemBioChem
18
2323-2327
2017
Plenodomus lingam (Q6Q874)
brenda
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