Information on EC 2.5.1.1 - dimethylallyltranstransferase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.5.1.1
-
RECOMMENDED NAME
GeneOntology No.
dimethylallyltranstransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + geranyl diphosphate
show the reaction diagram
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(3R)-linalool biosynthesis
-
-
(3S)-linalool biosynthesis
-
-
all-trans-farnesol biosynthesis
-
-
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
bisabolene biosynthesis (engineered)
-
-
geranyl diphosphate biosynthesis
-
-
ipsdienol biosynthesis
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linalool biosynthesis I
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Metabolic pathways
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mono-trans, poly-cis decaprenyl phosphate biosynthesis
-
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stellatic acid biosynthesis
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Terpenoid backbone biosynthesis
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trans, trans-farnesyl diphosphate biosynthesis
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viridicatumtoxin biosynthesis
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isoprenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:isopentenyl-diphosphate dimethylallyltranstransferase
This enzyme will not accept larger prenyl diphosphates as efficient donors.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
dual geranyl/farnesyl diphosphate synthase
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
cultivar Dhawal
UniProt
Manually annotated by BRENDA team
small subunit of GPP synthase
UniProt
Manually annotated by BRENDA team
mountain pine beetle
UniProt
Manually annotated by BRENDA team
bifunctional geranyl diphosphate synthase EC 2.5.1.1 and farnesyl diphosphate synthase EC 2.5.1.10
-
-
Manually annotated by BRENDA team
bifunctional enzyme: geranyldiphosphate synthase/myrcene synthase
SwissProt
Manually annotated by BRENDA team
bifunctional geranyl diphosphate synthase EC 2.5.1.1 and farnesyl diphosphate synthase EC 2.5.1.10
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
physiological function
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(Z)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(Z)-ethynylfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
sole product with wild-type, yield is 21.9% Z-ethynylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
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-
cyclohexylideneethyl diphosphate + 2-cyclohexenylethyl diphosphate
(cyclohexylideneethyl)-cyclohexylideneethyl diphosphate
show the reaction diagram
-
-
relative yield 0.8%
-
?
cyclohexylideneethyl diphosphate + isopentenyl diphosphate
10-cyclohexyliden-3,7-dimethyldeca-2,6-dien-1-ol + ?
show the reaction diagram
dimethylallyl diphosphate + (R)-benzodiazepinedione
aszonalenin + diphosphate
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E)-geranyl diphosphate + diphosphate
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate
(E,E)-farnesyl diphosphate + geranyl diphosphate + diphosphate
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
show the reaction diagram
-
in the presence of Mg2+
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
show the reaction diagram
diphosphate + farnesyl diphosphate
?
show the reaction diagram
diphosphate + geranyl diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate
show the reaction diagram
geranyl diphosphate + (3S)-3-(1H-indol-3-ylmethyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione
(3S)-3-([6-[(2Z)-2-ethylidene-6-methylhept-5-en-1-yl]-1H-indol-3-yl]methyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione + (3S)-3-([7-[(2Z)-7-methylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione + diphosphate
show the reaction diagram
-
-
31% + 60% yield
-
?
geranyl diphosphate + (3S,6R)-3-(4-hydroxybenzyl)-6-(1H-indol-3-ylmethyl)piperazine-2,5-dione
(3R,6S)-3-([6-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione + (3R,6S)-3-([7-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione + diphosphate
show the reaction diagram
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-
32% + 13% yield
-
?
geranyl diphosphate + (3S,6S)-3,6-bis(1H-indol-3-ylmethyl)piperazine-2,5-dione
(3S,6S)-3-([6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-[(1H-indol-3-yl)methyl]piperazine-2,5-dione + (3S,6S)-3-([7-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-[(1H-indol-3-yl)methyl]piperazine-2,5-dione + diphosphate
show the reaction diagram
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-
15% + 35% yield
-
?
geranyl diphosphate + (3S,6S)-3-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)piperazine-2,5-dione
(3S,6S)-3-([6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-(2-methylpropyl)piperazine-2,5-dione + (3S,6S)-3-([7-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-(2-methylpropyl)piperazine-2,5-dione + diphosphate
show the reaction diagram
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-
15% + 57% yield
-
?
geranyl diphosphate + (3S,6S)-3-(4-hydroxybenzyl)-6-(1H-indol-3-ylmethyl)piperazine-2,5-dione
(3R,6R)-3-([6-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione + (3S,6S)-3-([7-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-1H-indol-3-yl]methyl)-6-[(4-hydroxyphenyl)methyl]piperazine-2,5-dione + diphosphate
show the reaction diagram
-
-
9% + 24% yield
-
?
geranyl diphosphate + (R)-benzodiazepinedione
(3R)-3-([6-[(2Z)-2-ethylidene-6-methylhept-5-en-1-yl]-1H-indol-3-yl]methyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione + diphosphate
show the reaction diagram
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-
88% yield
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
show the reaction diagram
methoxymethoxydimethylallyl diphosphate + isopentenyl diphosphate
methoxymethoxygeranyl diphosphate + diphosphate
show the reaction diagram
propoxygeranyl diphosphate + isopentenyl diphosphate
propoxyfarnesyl diphosphate + diphosphate
show the reaction diagram
vinyldimethylallyl diphosphate + isopentenyl diphosphate
vinylgeranyl diphosphate + vinylfarnesyl diphosphate + diphosphate
show the reaction diagram
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14.3% vinylgeranyl diphosphate plus 23.3% vinylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
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additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
show the reaction diagram
Q17F78
-
in the presence of Mg2+
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
diphosphate + geranyl diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate
show the reaction diagram
additional information
?
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-
in vitro, but not in vivo, enzyme shows additional geranylgeranyl diphosphate synthase activity, EC 2.5.1.29
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
the enzyme is inactive without adding divalent metal cations
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
isopentenyl diphosphate
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substrate inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.008 - 1.103
dimethylallyl diphosphate
0.02
farnesyl diphosphate
-
at pH 7.5 and 30°C
0.008
geranyl diphosphate
-
at pH 7.5 and 30°C
0.00084 - 0.163
isopentenyl diphosphate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.085 - 1.4
dimethylallyl diphosphate
0.4
farnesyl diphosphate
Corynebacterium glutamicum
-
at pH 7.5 and 30°C
0.1
geranyl diphosphate
Corynebacterium glutamicum
-
at pH 7.5 and 30°C
0.012 - 1.1
isopentenyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
140
dimethylallyl diphosphate
Corynebacterium glutamicum
-
at pH 7.5 and 30°C
157
34
farnesyl diphosphate
Corynebacterium glutamicum
-
at pH 7.5 and 30°C
171
9
geranyl diphosphate
Corynebacterium glutamicum
-
at pH 7.5 and 30°C
175
140
isopentenyl diphosphate
Corynebacterium glutamicum
-
at pH 7.5 and 30°C
113
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.573
isopentenyl diphosphate
-
fixed substrate dimethylallyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.63
-
calculated from sequence
9
calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
protein is localized to epithelial cells surrounding the traumatic resin ducts
Manually annotated by BRENDA team
expression is restricted to wood and bark
Manually annotated by BRENDA team
of sapling
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
x * 40000, SDS-PAGE of recombinant protein
45800
-
2 * 45800, the enzyme is always present as a dimer regardless of the added cofactor, in the case of Mg2+, the dimeric protein possesses the largest volume (93800 Da), most likely due to a more relaxed conformation. With Co2+, the enzyme seems to have a more compact conformation (87600 Da), which may be responsible for the change in product spectrum calculated from sequence
87600
-
enzyme-Co2+ complex, gel filtration
93800
-
enzyme-Mg2+ complex, gel filtration
158000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 45800, the enzyme is always present as a dimer regardless of the added cofactor, in the case of Mg2+, the dimeric protein possesses the largest volume (93800 Da), most likely due to a more relaxed conformation. With Co2+, the enzyme seems to have a more compact conformation (87600 Da), which may be responsible for the change in product spectrum calculated from sequence
heterodimer
heterotetramer
Q9SBR3 and Q9SBR4
-
homodimer
-
-
homotetramer
tetramer
-
enzyme forms a heterotetramer of two catalytic large plus two regulatory small subunits, crystallization data.
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular dynamics simulations for wild-type and mutants Q107E, L110W, Q107F, Q107F/L110A, L110A
enzyme forms a heterotetramer of two catalytic large plus two regulatory small subunits. No activity is detected for individually expressed large or small subunits
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
-
the enzyme is stable at temperature below 50°C, while after 1 h at 40°C, the enzyme activity is reduced by about 80%
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cobalt column chromatography, and gel filtration
Ni-NTA column chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expresion in Escherichia coli after truncation of the signal sequence at the 5'-end of the coding region
-
expressed in Camelina sativa
-
expressed in Escherichia coli
Q9SBR3 and Q9SBR4
expressed in Escherichia coli strain C41
expression in Escherichia coli
expression in Escherichia coli and in Picea abies embryogenic tissue
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
in bark tissues after methyl jasmonate spraying, isoform IDS1 shows increased transcript level at the site of treatment
-
treatment with methyl jasmonate dramatically increases expression level in sapling
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L110A
complete loss of activity
L110W
about 50% decrease in reaction rate, increase in production of geranyl diphosphate
Q107E
increase in production of geranyl diphosphate
Q107F
increase in production of farnesyl diphosphate
Y81D
-
mutant yields higher condensation products than wild-type
DelP173/DelP174
decrease in reaction rate
G257D/P174C
little effect on reactionrate, no effect on product composition
I161M
little effect on reactionrate, no effect on product composition
I235T
decrease in reactionrate, single product is geranyldiphosphate
L180F
little effect on reactionrate, product composition is about 98% geranyldiphosphate, 12% geranygeranyl diphosphate
L180F/P174C
little effect on reactionrate, product composition is about 98% geranyldiphosphate, 12% geranygeranyl diphosphate
L273F
decrease in reactionrate, single product is geranyl diphosphate
M159I
little effect on reactionrate, no effect on product composition
M165C
little effect on reactionrate, no effect on product composition
M165Y
little effect on reactionrate, product composition is about 90% geranyldiphosphate, 10% farnesyl diphosphate
M175I
little effect on reactionrate, product composition is about 95% geranyldiphosphate, 3% farnesyl diphosphate, 25% geranygeranyl diphosphate
M175I/P174C
little effect on reactionrate, single product is geranyldiphosphate
M175I/P174S
little effect on reactionrate, no effect on product composition
P174C
little effect on reactionrate, no effect on product composition
P174S
little effect on reactionrate, no effect on product composition
V227M
decrease in reactionrate
V240L
decrease in reactionrate, no effect on product composition
Y81D
-
contrary to wild-type, reaction of (Z)-ethynyldimethylallyl diphosphate plus isopentenyl diphosphate yields a mixture of products ethynylgeranyl, ethynylfarnesyl, and ethynylgeranylgeranyl diphosphates
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