Information on EC 2.5.1.1 - dimethylallyltranstransferase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Mark a special word or phrase in this record:
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)


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

EC NUMBER
COMMENTARY
2.5.1.1
-
RECOMMENDED NAME
GeneOntology No.
dimethylallyltranstransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + geranyl diphosphate
show the reaction diagram
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
all-trans-farnesol biosynthesis
-
Biosynthesis of secondary metabolites
-
bisabolene biosynthesis
-
geranyl diphosphate biosynthesis
-
ipsdienol biosynthesis
-
linalool biosynthesis I
-
linalool biosynthesis II
-
Metabolic pathways
-
mono-trans, poly-cis decaprenyl phosphate biosynthesis
-
superpathway of linalool biosynthesis
-
Terpenoid backbone biosynthesis
-
trans, trans-farnesyl diphosphate biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:isopentenyl-diphosphate dimethylallyltranstransferase
This enzyme will not accept larger prenyl diphosphates as efficient donors.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
(E)-geranyl diphosphate synthase
L0T701
-
(E)-geranyl diphosphate synthase
L0T701
-
-
GPP synthase
-
-
GPP synthase
Q6QLU5
-
GPP synthase
Q95BR4
-
GPP synthase
-
-
GPPS
Q6QLU5
-
GPPS
Q95BR4
-
GPPS
-
-
IDS1
-
isoform
IDS2
-
isoform
isoprenyl diphosphate synthase
-
-
isoprenyl diphosphate synthase
D2IT07
-
Rv0989c
L0T701
gene name
Rv0989c
L0T701
gene name
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
dual geranyl/farnesyl diphosphate synthase
UniProt
Manually annotated by BRENDA team
small subunit of GPP synthase
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
small subunit of GPP synthase
UniProt
Manually annotated by BRENDA team
dual geranyl/farnesyl diphosphate synthase
UniProt
Manually annotated by BRENDA team
bifunctional geranyl diphosphate synthase and geranylgeranyl diphosphate synthase
UniProt
Manually annotated by BRENDA team
Norway spruce
-
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
metabolism
L0T701, -
the enzyme is able to provide the geranyl diphosphate precursor required for efficient production of both double bond isomers of farnesyl diphosphate in Mycobacterium tuberculosis
metabolism
-
the enzyme is able to provide the geranyl diphosphate precursor required for efficient production of both double bond isomers of farnesyl diphosphate in Mycobacterium tuberculosis
-
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 ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
-
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
-
-
double condensation product, relative yield 23.1%
-
?
cyclohexylideneethyl diphosphate + isopentenyl diphosphate
10-cyclohexyliden-3,7-dimethyldeca-2,6-dien-1-ol + ?
show the reaction diagram
-
-
double condensation product, relative yield 3.0%
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
D2IT07
-
geranylgeranyl diphosphate activity of enzyme leads to additional production of geranylgeranyl diphosphate. The ratio of geranyl diphosphate to geranylgeranyl diphosphate produced averages approximately 9:1. No synthesis of farnesyl diphosphate
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
-
-
relative yield 100%
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
-, Q58GE8
bifunctional enzyme: geranyldiphosphate synthase (EC 2.5.1.1)/myrcene synthase (EC 4.2.3.15). When the recombinant enzyme is incubated with dimethylallyl diphosphate and isopentenyl diphosphate as cosubstrates, the level of geranyl diphosphate formed is approximately tenfold higher than the level of myrcene formed. The data suggest that geranyl diphosphate is a free intermediate in myrcene production
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial. Geranyl diphosphate is needed for the de novo synthesis of the cyclopentanoid monoterpene iridoids, defensive compounds that are produced during the entire larval stage of Phaedon cochleariae, the enzyme is bifunctional and produces (2E,6E)-farnesyl diphosphate or geranyl diphosphate from dimethylallyl diphosphate and isopentenyl diphosphate depending on the divalent metal cofactor present. The enzyme is far more active with Co2+ as an additive than with any other tested metal ion. In the presence of Co2+ or Mn2+, with dimethylallyl diphosphate as a cosubstrate, it produces about 96% geranyl diphosphate and only 4% farnesyl diphosphate. In contrast, with Mg2+ as an additive, the enzyme produces 18% geranyl diphosphate and farnesyl diphosphate
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
show the reaction diagram
Q95BR4
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
show the reaction diagram
Q6QLU5
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
show the reaction diagram
-
-
isoform IDS1 shows 90% yield, isoform IDS2 shows 100% yield
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E,E)-farnesyl diphosphate + geranyl diphosphate + diphosphate
show the reaction diagram
Q1X876
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E,E)-farnesyl diphosphate + geranyl diphosphate + diphosphate
show the reaction diagram
Q1X877
-
ratio geranyl diphosphate/farnesyl diphosphate is about 2:1
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E)-geranyl diphosphate + diphosphate
show the reaction diagram
L0T701, -
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E)-geranyl diphosphate + diphosphate
show the reaction diagram
L0T701
-
-
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
show the reaction diagram
-
-
relative yield 13.6%
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
show the reaction diagram
-
-
relative yield 42.2%
-
?
methoxymethoxydimethylallyl diphosphate + isopentenyl diphosphate
methoxymethoxygeranyl diphosphate + diphosphate
show the reaction diagram
-
-
yield is 1% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
?
propoxygeranyl diphosphate + isopentenyl diphosphate
propoxyfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
yield is 3% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate, and 63% yield for mutant Y81D, plus 6% of propoxygeranylgeranyl diphosphate
-
?
propoxygeranyl diphosphate + isopentenyl diphosphate
propoxyfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
yield is 62% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
?
vinyldimethylallyl diphosphate + isopentenyl diphosphate
vinylgeranyl diphosphate + vinylfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
14.3% vinylgeranyl diphosphate plus 23.3% vinylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
-
methoxymethoxydimethylallyl diphosphate + isopentenyl diphosphate
methoxymethoxygeranyl diphosphate + diphosphate
show the reaction diagram
-
-
yield is 5% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate. Mutant Y81D yields methoxymethoxyfarnesyl diphosphate with high efficiency
-
?
additional information
?
-
-
in vitro, but not in vivo, enzyme shows additional geranylgeranyl diphosphate synthase activity, EC 2.5.1.29
-
-
-
additional information
?
-
Q1X876
enzyme is able to produce farnesyl phosphate directly from geranyl phosphate, activity of farnesylgeranyltransferase
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial. Geranyl diphosphate is needed for the de novo synthesis of the cyclopentanoid monoterpene iridoids, defensive compounds that are produced during the entire larval stage of Phaedon cochleariae
-
-
?
additional information
?
-
-
in vitro, but not in vivo, enzyme shows additional geranylgeranyl diphosphate synthase activity, EC 2.5.1.29
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Co2+
-
with dimethylallyl diphosphate and isopentenyl diphosphate the enzyme is far more active with Co2+ as an additive than with any other tested metal ion. In the presence of Co2+ or Mn2+, with dimethylallyl diphosphate as a cosubstrate, the enzyme produces about 96% geranyl diphosphate and only 4% farnesyl diphosphate. In contrast, with Mg2+ as an additive, PcIDS1 produces 18% geranyl diphosphate and 82% farnesyl diphosphate
Mg2+
D2IT07
required, activity reaches its highest value at 10 mM MgCl2. At 5 or 15 mM MgCl2, activity is about 65% of maximum
Mg2+
-
with dimethylallyl diphosphate and isopentenyl diphosphate the enzyme is far more active with Co2+ as an additive than with any other tested metal ion. In the presence of Co2+ or Mn2+, with dimethylallyl diphosphate as a cosubstrate, the enzyme produces about 96% geranyl diphosphate and only 4% farnesyl diphosphate. In contrast, with Mg2+ as an additive, PcIDS1 produces 18% geranyl diphosphate and 82% farnesyl diphosphate
additional information
-
the enzyme is inactive without adding divalent metal cations
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
isopentenyl diphosphate
-
substrate inhibition
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0116
-
dimethylallyl diphosphate
-
fixed substrate isopentenyl diphosphate (0.015 mM), pH and temperature not specified in the publication, metal cofactor: Co2+
0.058
-
dimethylallyl diphosphate
L0T701, -
in 50 mM sodium phosphate (pH 7.0), at 37C
0.39
-
dimethylallyl diphosphate
D2IT07
-
1.103
-
dimethylallyl diphosphate
-
fixed substrate isopentenyl diphosphate (0.015 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
0.00084
-
isopentenyl diphosphate
-
fixed substrate dimethylallyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Co2+
0.0118
-
isopentenyl diphosphate
-
fixed substrate dimethylallyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
0.163
-
isopentenyl diphosphate
L0T701, -
in 50 mM sodium phosphate (pH 7.0), at 37C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.085
-
dimethylallyl diphosphate
L0T701, -
in 50 mM sodium phosphate (pH 7.0), at 37C
1.4
-
dimethylallyl diphosphate
D2IT07
-
0.012
-
isopentenyl diphosphate
L0T701, -
in 50 mM sodium phosphate (pH 7.0), at 37C
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.573
-
isopentenyl diphosphate
-
fixed substrate dimethylallyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
8.63
-
-
calculated from sequence
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
D2IT07
of sapling
Manually annotated by BRENDA team
D2IT07
protein is localized to epithelial cells surrounding the traumatic resin ducts
Manually annotated by BRENDA team
D2IT07
expression is restricted to wood and bark
Manually annotated by BRENDA team
D2IT07
of sapling
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
Corynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
Corynebacterium glutamicum (strain ATCC 13032 / DSM 20300 / JCM 1318 / LMG 3730 / NCIMB 10025)
Rhizobium loti (strain MAFF303099)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
87600
-
-
enzyme-Co2+ complex, gel filtration
93800
-
-
enzyme-Mg2+ complex, gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
D2IT07
x * 40000, SDS-PAGE of recombinant protein
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
-
-
heterodimer
Q6QLU5
-
heterodimer
Q95BR4
-
tetramer
-
enzyme forms a heterotetramer of two catalytic large plus two regulatory small subunits, crystallization data.
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
molecular dynamics simulations for wild-type and mutants Q107E, L110W, Q107F, Q107F/L110A, L110A
Q1X877
enzyme forms a heterotetramer of two catalytic large plus two regulatory small subunits. No activity is detected for individually expressed large or small subunits
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Ni-NTA column chromatography
L0T701, -
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli
-, Q58GE8
expressed in Escherichia coli strain C41
L0T701, -
expresion in Escherichia coli after truncation of the signal sequence at the 5'-end of the coding region
-
expression in Escherichia coli and in Picea abies embryogenic tissue
D2IT07
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
treatment with methyl jasmonate dramatically increases expression level in sapling
D2IT07
in bark tissues after methyl jasmonate spraying, isoform IDS1 shows increased transcript level at the site of treatment
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
L110A
Q1X877
complete loss of activity
L110W
Q1X877
about 50% decrease in reaction rate, increase in production of geranyl diphosphate
Q107E
Q1X877
increase in production of geranyl diphosphate
Q107F
Q1X877
increase in production of farnesyl diphosphate
Y81D
-
mutant yields higher condensation products than wild-type
DelP173/DelP174
D2IT07
decrease in reaction rate
G257D/P174C
D2IT07
little effect on reactionrate, no effect on product composition
I161M
D2IT07
little effect on reactionrate, no effect on product composition
I235T
D2IT07
decrease in reactionrate, single product is geranyldiphosphate
L180F
D2IT07
little effect on reactionrate, product composition is about 98% geranyldiphosphate, 12% geranygeranyl diphosphate
L180F/P174C
D2IT07
little effect on reactionrate, product composition is about 98% geranyldiphosphate, 12% geranygeranyl diphosphate
L273F
D2IT07
decrease in reactionrate, single product is geranyl diphosphate
M159I
D2IT07
little effect on reactionrate, no effect on product composition
M165C
D2IT07
little effect on reactionrate, no effect on product composition
M165Y
D2IT07
little effect on reactionrate, product composition is about 90% geranyldiphosphate, 10% farnesyl diphosphate
M175I
D2IT07
little effect on reactionrate, product composition is about 95% geranyldiphosphate, 3% farnesyl diphosphate, 25% geranygeranyl diphosphate
M175I/P174C
D2IT07
little effect on reactionrate, single product is geranyldiphosphate
M175I/P174S
D2IT07
little effect on reactionrate, no effect on product composition
P174C
D2IT07
little effect on reactionrate, no effect on product composition
P174S
D2IT07
little effect on reactionrate, no effect on product composition
V227M
D2IT07
decrease in reactionrate
V240L
D2IT07
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