Information on EC 2.5.1.29 - geranylgeranyl diphosphate synthase

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

EC NUMBER
COMMENTARY hide
2.5.1.29
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RECOMMENDED NAME
GeneOntology No.
geranylgeranyl diphosphate synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + geranylgeranyl diphosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alkenyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
brassicicene C biosynthesis
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fusicoccin A biosynthesis
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geranylgeranyl diphosphate biosynthesis
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methyl phomopsenoate biosynthesis
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ophiobolin F biosynthesis
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paspaline biosynthesis
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plaunotol biosynthesis
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stellatic acid biosynthesis
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isoprenoid biosynthesis
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Terpenoid backbone biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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Biosynthesis of antibiotics
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase
Some forms of this enzyme will also use geranyl diphosphate and dimethylallyl diphosphate as donors; it will not use larger prenyl diphosphates as efficient donors.
CAS REGISTRY NUMBER
COMMENTARY hide
9032-58-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Automatic Mining of ENzyme DAta
animal
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archaebacterium
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UniProt
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
MF730-N6
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Manually annotated by BRENDA team
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Vitis vinifera x Vitis vinifera
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Manually annotated by BRENDA team
Xanthophyllomyces dendrorhous CBS6938, ATCC96594
a basidiomycetous yeast, the sexual state of Phaffia rhodozyma, gene crtE
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
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depletion of geranylgeranyl diphosphate by inhibitor statins leads to accumulation of farnesyl diphosphate, which activates nuclear hormone receptors stimulating osteoblast differentiation and bone formation. Statins directly inhibit HMG-CoA reductase, the first step of the isoprenoid biosynthesis pathway
metabolism
physiological function
additional information
GGPPS gene can be a good model to study the regulatory mechanisms controlling phorbol esters accumulation at the transcriptional level
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E)-3,7-dimethyl-2-octenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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62% of activity with geranyl diphosphate
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?
(2E)-3-methyl-2,6-heptadienyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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24% of activity with geranyl diphosphate
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?
(2E)-3-methyl-2-butenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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21.5% of activity with geranyl diphosphate
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?
(2E)-3-methyl-2-hexenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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95% of activity with geranyl diphosphate
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?
(2E)-3-methyl-2-pentenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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63% of activity with geranyl diphosphate
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?
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
(E)-3-methyl-2-dodecenyl diphosphate + isopentenyl diphosphate
(2E,5E)-3,6-dimethylpentadeca-2,5-dien-1-yl diphosphate + diphosphate
show the reaction diagram
(E,E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
(E,E)-farnesyl diphosphate + isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
3,8-dimethyl-2-nonenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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59% of activity with dimethylallyl diphosphate
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?
3-methyl-2-alkenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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a number of 3-methyl-2-alkenyl diphosphates ranging in carbon number from 6 to 13 act as substrates
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?
6,7-dihydrogeranyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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87% of activity with dimethylallyl diphosphate
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?
8,8'-bisnorgeranyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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107% of activity with dimethylallyl diphosphate
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?
cis-3-methyl-2-hexenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
cyclopentylideneethyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
dimethylallyl diphosphate + 3 isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
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geranyl diphosphate activity of enzyme leads to additional production of geranyl diphosphate. The ratio of geranyl diphosphate to geranylgeranyl diphosphate produced averages approximately 9:1. No synthesis of farnesyl diphosphate
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?
dimethylallyl diphosphate + 3 isopentenyl diphosphate
geranylgeranyl diphosphate + 3 diphosphate
show the reaction diagram
dimethylallyl diphosphate + 3 isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate
? + diphosphate
show the reaction diagram
bifunctional enzyme EC2.5.1.29/EC2.5.1.10, the FPP/GGPP product ratio increases with the rise of the reaction temperature
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?
dimethylallyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + farnesyl diphosphate + geranylgeranyl diphosphate + diphosphate
show the reaction diagram
large subunit alone
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?
E-3-methyl-2-undecenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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53% of the activity with farnesyl diphosphate
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?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
farnesyl diphosphate + isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
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?
geranyl diphosphate + 2 isopentenyl diphosphate
geranylgeranyl diphosphate + 2 diphosphate
show the reaction diagram
geranyl diphosphate + 2 isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
geranyl diphosphate + dimethylallyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
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?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
show the reaction diagram
trans,trans-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
trans-3-methyl-2-octenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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similar activity as with dimethylallyl diphosphate
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?
trans-3-methyl-2-pentenyl diphosphate + isopentenyl diphosphate
?
show the reaction diagram
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33% of activity with dimethylallyl 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
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
Q9V305
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?
(E,E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
(E,E)-farnesyl diphosphate + isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
dimethylallyl diphosphate + 3 isopentenyl diphosphate
geranylgeranyl diphosphate + 3 diphosphate
show the reaction diagram
dimethylallyl diphosphate + 3 isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
Q9V305
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?
geranyl diphosphate + 2 isopentenyl diphosphate
geranylgeranyl diphosphate + 2 diphosphate
show the reaction diagram
geranyl diphosphate + 2 isopentenyl diphosphate
geranylgeranyl diphosphate + diphosphate
show the reaction diagram
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
show the reaction diagram
Q76CZ2
bifunctional enzyme EC2.5.1.29/EC2.5.1.10, the FPP/GGPP product ratio increases with the rise of the reaction temperature. The enzyme contributes to adjust the membrane composition to the cell growth temperature modulating its substrate and product specificities
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?
trans,trans-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + geranylgeranyl diphosphate
show the reaction diagram
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
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activates, less effective than Mg2+
MgCl2
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Km value 0.51 mM for isoform GGPPS1, 0.19 mM for isoform GGPPS2
additional information
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monovalent cations at low concentrations, i.e. 50 mM, enhance activity, at high concentrations, i.e. 400 mM, they are inhibitory, except for K+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2E,6E)-farnesyl-bis(phosphonic acid)
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both inhibition of in vitro reaction as well as of cellular geranylgeranylation
(2E,6E)-farnesyl-geranyl-bis(phosphonic acid)
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both inhibition of in vitro reaction as well as of cellular geranylgeranylation
(2E,6Z)-farnesyl-bis(phosphonic acid)
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both inhibition of in vitro reaction as well as of cellular geranylgeranylation
(3E,7Z)-4,8,12-trimethyl-1-phosphonitotrideca-3,7,11-trienylphosphonate
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(3Z,7E)-4,8,12-trimethyl-1-phosphonitotrideca-3,7,11-trienylphosphonate
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(3Z,7Z)-4,8,12-trimethyl-1-phosphonitotrideca-3,7,11-trienylphosphonate
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(6Z,11E)-2,6,12,16-tetramethylheptadeca-2,6,11,15-tetraene-9,9-diyldiphosphonate
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(6Z,11Z)-2,6,12,16-tetramethylheptadeca-2,6,11,15-tetraene-9,9-diyldiphosphonate
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(E,E,E)-geranylgeranyl diphosphate
(Z)-2,8,12-trimethyltrideca-2,7,11-triene-5,5-diyldiphosphonate
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(Z,E,E)-Geranylgeranyl diphosphate
1-hydroxydecane-1,1-bisphosphonate
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IC50: 720 nM
3-azafarnesyl diphosphate
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0.00074 mM, 50% inhibition
3-azageranyl diphosphate
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0.24 mM, 50% inhibition
3-azageranylgeranyl diphosphate
3-azahomofarnesyl diphosphate
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0.00031 mM, 50% inhibition
3-azahomogeranylgeranyl diphosphate
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0.00037 mM, 50% inhibition
4-[(5-[[4-(3-chlorophenyl)-3-oxopiperazin-1-yl]methyl]-1H-imidazol-1-yl)methyl]benzonitrile
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a dual prenyl transferase inhibitor that has advanced to clinical trials
Aminophenylethyl diphosphate
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bis[(6E)-2,6-dimethylnona-2,6-diene-9,9-diyl]bis(phosphonic acid)
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both inhibition of in vitro reaction as well as of cellular geranylgeranylation
digeranyl bisphosphonate
diphosphate
farnesyl diphosphate
geranylgeranyl diphosphate
homorisedronate
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i.e. NE58051, 0.41 mM, 50% inhibition
ibandronate
Li+
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400 mM, 72% inhibition, slight activation at 50 mM
N-([5-[(1H-imidazol-4-ylmethyl)amino]-2'-methylbiphenyl-2-yl]carbonyl)-L-leucine
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N-[methyl(4-phenylbutyl)]-3-aminopropyl-1-hydroxy-1,1-bisphosphonate
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the bisphosphonate binds only to the GGPP product inhibitory site
NH4+
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20 mM, 20% inhibition
nitrogen-containing bisphosphonates
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nitrogeneous biphosphonates
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-
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p-chloromercuribenzoate
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1 mM, 90% inhibition, 30% inhibition in the presence of 800 mM KCl
pamidronate
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0.18 mM, 50% inhibition
risedronate
Triton X-100
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stimulates farnesyl-transferring activity, inhibits dimethylallyl-transferring activity
zoledronate
[(6E,11E)-2,6,12,16-tetramethylheptadeca-2,6,11,15-tetraene-9,9-diyl]bis(phosphonic acid)
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[1-hydroxy-2-(1,1':4',1''-terphenyl-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
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[1-hydroxy-2-(3-pyridinyl)ethylidene]bisphosphonic acid
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a nitrogen-containing bisphosphonate
[1-hydroxy-2-(pyridin-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
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additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NH4+
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50 mM, enhances activity approx. 13fold
octyl glucoside
Triton X-100
Tween 20
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at 0.2%
Tween 80
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0018 - 0.0073
(2E,6E)-farnesyl diphosphate
0.0014 - 0.0044
(E,E)-farnesyl diphosphate
0.00095 - 0.39
dimethylallyl diphosphate
0.0005 - 0.121
farnesyl diphosphate
0.00072 - 0.022
geranyl diphosphate
0.0003 - 0.267
isopentenyl diphosphate
0.0034 - 0.035
Mg2+
0.0004 - 0.055
trans,trans-farnesyl diphosphate
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.8
(2E,6E)-farnesyl diphosphate
Plasmodium vivax
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pH 7.7, 37C, recombinant PvGGPPS
0.000042 - 0.025
(E,E)-farnesyl diphosphate
0.5 - 1.4
dimethylallyl diphosphate
3.3
farnesyl diphosphate
Taxus canadensis
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-
0.5 - 2.1
geranyl diphosphate
0.8
isopentenyl diphosphate
Plasmodium vivax
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pH 7.7, 37C, recombinant PvGGPPS
0.204 - 8.4
trans,trans-farnesyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
100
(2E,6E)-farnesyl diphosphate
Plasmodium vivax
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pH 7.7, 37C, recombinant PvGGPPS
81
200
dimethylallyl diphosphate
Plasmodium vivax
-
pH 7.7, 37C, recombinant PvGGPPS
157
300
geranyl diphosphate
Plasmodium vivax
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pH 7.7, 37C, recombinant PvGGPPS
175
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0012
(E,E,E)-geranylgeranyl diphosphate
0.025
geranylgeranyl diphosphate
-
pH 7.7, 37C, recombinant enzyme, versus trans,trans-farnesyl diphosphate
0.000016
ibandronate
-
pH 7.7, 37C, recombinant PvGGPPS
0.0000107
zoledronate
-
pH 7.7, 37C, recombinant PvGGPPS
0.0000124
[1-hydroxy-2-(3-pyridinyl)ethylidene]bisphosphonic acid
-
pH 7.7, 37C, recombinant PvGGPPS
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0001
(2E,6E)-farnesyl-bis(phosphonic acid)
Homo sapiens
-
pH 7.5, 37C
0.0003
(2E,6E)-farnesyl-geranyl-bis(phosphonic acid)
Homo sapiens
-
pH 7.5, 37C
0.0006
(2E,6Z)-farnesyl-bis(phosphonic acid)
0.04