Information on EC 2.5.1.10 - (2E,6E)-farnesyl diphosphate synthase

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

EC NUMBER
COMMENTARY hide
2.5.1.10
-
RECOMMENDED NAME
GeneOntology No.
(2E,6E)-farnesyl diphosphate synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alkenyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
all-trans-farnesol biosynthesis
-
-
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
bisabolene biosynthesis (engineered)
-
-
isoprenoid biosynthesis
-
-
Metabolic pathways
-
-
methyl phomopsenoate biosynthesis
-
-
stellatic acid biosynthesis
-
-
Terpenoid backbone biosynthesis
-
-
trans, trans-farnesyl diphosphate biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate:isopentenyl-diphosphate geranyltranstransferase
Some forms of this enzyme will also use dimethylallyl diphosphate as a substrate. The enzyme will not accept larger prenyl diphosphates as efficient donors.
CAS REGISTRY NUMBER
COMMENTARY hide
37277-79-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
grand fir
-
-
Manually annotated by BRENDA team
dual geranyl/farnesyl diphosphate synthase
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Madagascar periwinkle
SwissProt
Manually annotated by BRENDA team
wintersweet
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Pumpkin
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
isoenzyme I and II
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(E)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(E)-ethynylfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
double condensation product. Yield is 0.8% E-ethynylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
?
(Z)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(Z)-ethynylfarnesyl diphosphate + diphosphate
show the reaction diagram
8-acetoxygeranyl diphosphate + isopentenyl diphosphate
diphosphate + 12-acetoxyfarnesyl diphosphate
show the reaction diagram
8-hydroxygeranyl diphosphate + isopentenyl diphosphate
hydroxyfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
mutants Y81S and Y81D, produce additionally hydroxygeranylgeranyl diphosphate plus a small amount of hydroxygeranylfarnesyl diphosphate
-
?
8-methoxygeranyl diphosphate + isopentenyl diphosphate
methoxyfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
mutants Y81S and Y81D, produce methoxygeranylgeranyl diphosphate as main product plus some methoxyfarnesyl 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
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
show the reaction diagram
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + diphosphate
show the reaction diagram
-
-
-
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
show the reaction diagram
-
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 82% farnesyl diphosphate
-
-
?
dimethylallyl diphosphate + geranyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate
(2E,6E)-farnesyl 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 + (2E,6E)-farnesyl diphosphate
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
show the reaction diagram
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
show the reaction diagram
-
-
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
show the reaction diagram
Pumpkin
-
less than 5% of the activity with dimethylallyl diphosphate
-
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
show the reaction diagram
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
show the reaction diagram
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (E,E)-farnesyl diphosphate
show the reaction diagram
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
show the reaction diagram
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
show the reaction diagram
isopentenyl diphosphate + geranyl diphosphate
(E,E)-farnesyl diphosphate + diphosphate
show the reaction diagram
-
-
-
?
isopentenyl diphosphate + geranyl diphosphate
diphosphate + farnesyl diphosphate
show the reaction diagram
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
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
vinylfarnesyl diphosphate + diphosphate
show the reaction diagram
-
-
sole product, yield is 29.9% vinylfarnesyl 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
-
-
additional information
?
-
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 + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
show the reaction diagram
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
dimethylallyl diphosphate + geranyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
show the reaction diagram
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial. Farnesyl diphosphate serves as precursor for various primary metabolites and juvenile required hormone
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
show the reaction diagram
-
key enzyme in isoprenoid biosynthesis
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
show the reaction diagram
-
key enzyme in isoprenoid biosynthesis
-
-
?
isopentenyl diphosphate + geranyl diphosphate
diphosphate + farnesyl diphosphate
show the reaction diagram
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
18% of Mg2+ activation at 0.5 mM, inhibition above
Fe2+
-
absolutely dependent on presence of divalent cation. Supports activity to a lower level than Mg2+
K+
-
stimulates with geranyl diphosphate as substrate
Ni2+
-
10% of Mg2+ activation at 0.5 mM, inhibition above
Zn2+
-
91% of Mg2+ activation at 0.5 mM, almost complete inhibition at 5 mM
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1-hydroxyheptane-1,1-diyl)bis(phosphonic acid)
-
-
(2-[[(2E)-2,6-dimethylhepta-2,5-dien-1-yl]amino]ethane-1,1-diyl)bis(phosphonic acid)
-
-
([Cu(II)(pamidronate)]H2O)n
-
-
-
([[6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]amino]methanediyl)bis(phosphonic acid)
-
-
([[6-(3-methoxyphenyl)pyridin-3-yl]amino]methanediyl)bis(phosphonic acid)
-
-
([[6-(thiophen-3-yl)pyridin-3-yl]amino]methanediyl)bis(phosphonic acid)
-
-
1-[(benzylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-dec-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-dodec-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-hept-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-hex-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-non-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-oct-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-pent-1-ylamino)ethyl] 1,1-bisphosphonic acid
-
-
1-[(n-tetradec-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(n-undec-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(prop-1-ylamino)ethyl] 1,1-bisphosphonic acid
1-[(prop-2-ylamino)ethyl] 1,1-bisphosphonic acid
3-(2-hydroxy-2,2-diphosphonoethyl)-2H-imidazo[1,2-a]pyridin-4-ium
-
-
alendronate
bacitracin
-
-
Ca2+
-
5 mM, 80% inhibition
diphosphate
-
0.66 mM, 50% inhibition
farnesyl diphosphate
-
0.06 mM, 50% inhibition
geranyl diphosphate
-
-
ibandronate
iodoacetamide
isopentenyl diphosphate
K+
-
500 mM, 63% inhibition in the presence of MgCl2
N-ethylmaleimide
-
8 mM, 54% inhibition
p-chloromercuribenzoic acid
-
0.15 mM, 882% inhibition of wild-type farnesyl diphosphate synthase, 11% inhibition of C73S/C289S mutant enzyme
p-hydroxymercuribenzoate
-
1 mM, 25% inhibition
pamidronate
Phenylglyoxal
-
-
risedronate
Triton X-100
-
above 0.2%
[(octylamino)methanediyl]bis(phosphonic acid)
-
-
[([6-[3-(trifluoromethyl)phenyl]pyridin-3-yl]amino)methanediyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[2-(1H-indazol-4-yl)pyridin-4-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-4-yl)pyridin-2-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-4-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-5-yl)pyridin-2-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-5-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-6-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-pyrazol-4-yl)pyridin-2-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-pyrazol-4-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[6-(1H-pyrazol-4-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-3-[(3-phenylpropyl)amino]propane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-3-[methyl(2-phenylethyl)amino]propane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-3-[methyl(4-phenylbutyl)amino]propane-1,1-diyl]bis(phosphonic acid)
-
-
[2-(3-chlorophenyl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-(3-fluorophenyl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-(cyclohexylamino)ethane-1,1-diyl]bisphosphonic acid
-
-
[2-(heptylamino)ethane-1,1-diyl]bis(phosphonic acid)
[2-(hexylamino)ethane-1,1-diyl]bis(phosphonic acid)
[2-(n-heptylamino)ethane-1,1-diyl]bisphosphonic acid
-
-
[2-(n-hexylamino)ethane-1,1-diyl]bisphosphonic acid
-
-
[2-(n-pentylamino)ethane-1,1-diyl]bisphosphonic acid
-
-
[2-(npropylamino)ethane-1,1-diyl]bisphosphonic acid
-
-
[2-[(2-methylprop-2-en-1-yl)amino]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-[2-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-4-yl]-1-fluoroethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-[5-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-3-yl]-1-fluoroethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-[6-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-2-yl]-1-fluoroethane-1,1-diyl]bis(phosphonic acid)
-
-
[6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid)
-
i.e. NE-10501, chiral analog of risedronate. Crystallization of human enzyme from a solution of racemic NE-10501 results in a complex containing the R enantiomer in the enzyme active site
[Co(II)(pamidronate)2(H2O)2]
-
-
-
[Co(II)(risedronate)2]
-
-
-
[Co(II)2(alendronate)4(H2O)2]
-
-
-
[Cu(II)(risedronate)2]
-
-
-
[Cu(II)2(alendronate)4(H2O)2]
-
-
-
[Mn(II)(pamidronate)2(H2O)2]
-
-
-
[Mn(II)(risedronate)2]
-
-
-
[Mn(II)2(alendronate)4(H2O)2]
-
-
-
[Ni(II)(pamidronate)2(H2O)2]
-
-
-
[Ni(II)(risedronate)2]
-
-
-
[Ni(II)2(alendronate)4(H2O)2]
-
-
-
additional information
-
neither iodoacetamide nor N-ethylmaleimide inhibits at concentration less than 5 mM
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,4-dithiothreitol
-
2 mM, 1.6fold stimulation
2-mercaptoethanol
-
10 mM, 1.2fold stimulation
dithioerythritol
-
-
dithiothreitol
-
2.5 mM, increases activity 2fold
NH4+
-
3fold stimulation with geranyl diphosphate as substrate; 5fold stimulation with dimethylallyl diphosphate as substrate
Triton X-100
Tween 80
-
0.5%, 2.3fold activation
additional information
-
not activated by Tween 20, Triton X-100, Chaps or Nonidet P-40
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0045 - 0.0666
dimethylallyl diphosphate
0.0705
farnesyl diphosphate
-
mutant enzyme L58A
0.0012 - 8.4
geranyl diphosphate
0.0015 - 130
isopentenyl diphosphate
0.0712
Mg2+
-
-
0.0445
Mn2+
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.2
geranyl diphosphate
Mycobacterium tuberculosis
-
pH 7.9, 37C
0.49
isopentenyl diphosphate
Mycobacterium tuberculosis
-
pH 7.9, 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.322
geranyl diphosphate
-
fixed substrate isopentenyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
0.0007 - 1.05
isopentenyl diphosphate
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00063
(1-hydroxyheptane-1,1-diyl)bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22C
0.000095
([Cu(II)(pamidronate)]H2O)n
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.001
1-[(benzylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
IC50 above 0.001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
0.000068 - 0.001
1-[(n-dec-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000093 - 0.000811
1-[(n-dodec-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000058 - 0.000095
1-[(n-hept-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000137 - 0.00049
1-[(n-hex-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.00043 - 0.00044
1-[(n-non-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000087 - 0.00101
1-[(n-oct-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.00008
1-[(n-pent-1-ylamino)ethyl] 1,1-bisphosphonic acid
Toxoplasma gondii
-
pH 7.4, 37C
0.000292 - 0.001
1-[(n-tetradec-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000856 - 0.000868
1-[(n-undec-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000038 - 0.000298
1-[(prop-1-ylamino)ethyl] 1,1-bisphosphonic acid
0.000013 - 0.000337
1-[(prop-2-ylamino)ethyl] 1,1-bisphosphonic acid
0.00064
3-(2-hydroxy-2,2-diphosphonoethyl)-2H-imidazo[1,2-a]pyridin-4-ium
Plasmodium vivax
-
pH 7.4, 22C
0.0044
alendronate
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
0.00134
pamidronate
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
0.000027 - 0.000074
risedronate
0.00049
[(octylamino)methanediyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22C
0.00045
[1-hydroxy-3-[(3-phenylpropyl)amino]propane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22C
0.0004
[1-hydroxy-3-[methyl(2-phenylethyl)amino]propane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22C
0.00061
[1-hydroxy-3-[methyl(4-phenylbutyl)amino]propane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22C
0.00063
[2-(3-chlorophenyl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
0.000058
[2-(heptylamino)ethane-1,1-diyl]bis(phosphonic acid)
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.00014 - 0.00135
[2-(hexylamino)ethane-1,1-diyl]bis(phosphonic acid)
0.000058
[2-(n-heptylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.00049
[2-(n-hexylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.00184
[2-(n-pentylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.000038
[2-(npropylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.0006295
[6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid)
Homo sapiens
-
racemat
0.000215
[Co(II)(pamidronate)2(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.0001
[Co(II)(risedronate)2]
Trypanosoma cruzi
-
IC50 above 0.0001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.05
[Co(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
IC50 above 0.05 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.000026
[Cu(II)(risedronate)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.000717
[Cu(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.000161
[Mn(II)(pamidronate)2(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.0000027
[Mn(II)(risedronate)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.000128
[Mn(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.000328
[Ni(II)(pamidronate)2(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.0000029
[Ni(II)(risedronate)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
0.000167
[Ni(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37C
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.04
-
isoenzyme II
0.06
-
isoenzyme I
0.35
-
C289F mutant enzyme at 55C
0.922
-
-
1.3
-
C73F mutant enzyme at 45C
2.61
-
wild-type enzyme at 45C
3.94
-
C289S mutant enzyme at 55C
3.97
-
C73S/C289S mutant enzyme at 55C
4.3
-
C73F mutant enzyme at 55C
4.69
-
wild-type enzyme at 55C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3 - 8.8
-
-
7.5 - 8
-
-
7.5
Pumpkin
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 8.5
-
approx. 45% of maximal activity at pH 5.5, approx. 60% of activity maximum at pH 8.5, emzyme I
7 - 10
-
active over the range pH 7-10
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.6
isoform FPPS2, calculated from amino acid sequence
7.5
isoform FPPS1, calculated from amino acid sequence
8.63
-
calculated from sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Pumpkin
-
-
Manually annotated by BRENDA team
and seed, high expression
Manually annotated by BRENDA team
hairy root and seed, high expression
Manually annotated by BRENDA team
and hairy root, high expression; and root, high expression
Manually annotated by BRENDA team
and leaf, low expression
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Agrobacterium fabrum (strain C58 / ATCC 33970)
Campylobacter jejuni (strain RM1221)
Erythrobacter sp. (strain OCh 114)
Erythrobacter sp. (strain OCh 114)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
Lactobacillus brevis (strain ATCC 367 / JCM 1170)
Lactobacillus brevis (strain ATCC 367 / JCM 1170)
Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513)
Methylococcus capsulatus (strain ATCC 33009 / NCIMB 11132 / Bath)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Roseobacter denitrificans (strain ATCC 33942 / OCh 114)
Roseobacter denitrificans (strain ATCC 33942 / OCh 114)
Streptococcus uberis (strain ATCC BAA-854 / 0140J)
Streptococcus uberis (strain ATCC BAA-854 / 0140J)
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
-
gel filtration, enzyme I, protein concentration 0.02 mg/ml
60000
-
gel filtration, enzyme II, protein concentration 0.02 mg/ml
67000
-
gel filtration
72500
-
gel filtration, protein concentration 25 mg/ml
74000
-
gel filtration
87600
-
enzyme-Co2+ complex, gel filtration
93800
-
enzyme-Mg2+ complex, gel filtration
103000
-
SDS-PAGE after cross-linking with dimethyl suberimidate
110000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
2 * 45500, isoform FPPS1, calculated from amino acid sequence; 2 * 45900, isoform FPPS2, calculated from amino acid sequence
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular dynamics simulations for wild-type and mutants Q107E, L110W, Q107F, Q107F/L110A, L110A
molecular modeling of structure based on PDB file 1FPS
-
crystallization of human enzyme from a solution of racemic [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid) results in a complex containing the R enantiomer in the enzyme active site. Contrary to known complexes of enzyme with risedronate, zoledronate, and minodronate, the complex with [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid) displays only one Mg2+ ion; in complex with chiral risedronate analog, [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid), i.e. NE-10501. The complex contains the R enantiomer in the enzymic active site, which is confirmed by docking studies. Presence of one Mg2+
-
in complex with Mg2+ and inhibitors, vapor diffusion method, using 100 mM sodium acetate, pH 4.6-5.2, 200 mM ammonium sulfate, and 2-10% (w/v) PEG 4K
-
in complex with substrate isopentenyl diphosphate and five nitrogen-containing bisphosphonate inhibitors. The C1-hydroxyl and the nitrogen-containing groups of the inhibitors alter the binding of isopentenyl diphosphate and the conformation of residues Y94 and Q167. binding of the inhibitors changes the binding properties of the second site of the dimer
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
-
wild-type: stable for 30 min, C73F mutant: complete loss of activity after 20 min
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
thiol reducing agents are detrimental for stability
-
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme seems to be susceptible to oxidation when treated with Cu2+, forming an intrasubunit disulfide bond rather than intersubunit bonds
-
638699
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, at least 1 week, no loss of activity
-
-80C, 3 months, no loss of activity
-
4C, 5 days, 36% loss of activity
-
4C, precipitate in neutral (NH4)2SO4 solution at 60% saturation, 1 year, 50-70% loss of activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, affinity chromatography
ammonium sulfate, Sephadex G 200, hydroxylapatite
Pumpkin
-
ammonium sulfate, Sephadex G-100, hydroxylapatite, DEAE-Sephadex A-50
-
anti-FLAG M2 affinity resin chromatography and nickel affinity column chromatography
-
DEAE-Sepharose, Mono Q, phenyl-Sepharose
-
HisTrap Ni2+ chelate affinity chromatography
-
Ni-NTA column chromatography
partial purification
-
recombinant protein
TALON resin Co2+ metal affinity column chromatography; TALON resin Co2+ metal affinity column chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
-
expressed in Escherichia coli ArcticExpress (DE3) RP cells
expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli DH5alpha cells
expressed in Saccharomyces cerevisiae
expression in Escherichia coli
expression in Escherichia coli after truncation of the signal sequence at the 5'-end of the coding region
-
expression in Mycobacterium smegmatis using a new mycobacterial expression vector that encodes an in-frame N-terminal affinity tag fusion with the protein of interest
-
expression of wild-type, S82F, S82Y, S82W, L83F, L83Y, I84F and I84Y mutant enzymes in Escherichia coli
-
overexpression of C73F, C289F, C73S, C289S and C73/C289S mutant enzyme in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
after treatment of hairy root with methyl jasmonate, mRNA is detected within 12 h and achieves a maximum after 24 h
enzyme expression in stage 2 of flower development is 22fold higher than in the stage 2, and these levels rise dramatically in the flower of stage 3 and 4, reaching a 113fold increase at stage 4
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
C289F
-
approx. 1/13 of wild-type activity at 55C
C289S
-
similar activity like wild-type
C73F
-
heat sensitive mutant
C73S
-
similar activity like wild-type
C73S/C289S
-
similar activity like wild-type
F220A
-
100000fold decrease in catalytic activity
I84F
-
7.2% of wild-type activity with dimethylallyl diphosphate
I84Y
-
similiar activity as wild-type
L83F
-
similiar activity as wild-type
L83Y
-
similiar activity as wild-type
Q221E
-
1000fold decrease in catalytic activity
R295V
-
no marked change in catalytic activity
S82F
-
produces exclusively geranyl diphosphate, i.e. the mutant enzyme has changed from a farnesyl diphosphate synthase to a geranyl diphosphate synthase
S82W
-
no prenyl transferase activity
S82Y
-
similiar activity as wild-type
K266I
the mutation abolishes the activities of isoform FPPS1; the mutation abolishes the activities of isoform FPPS2
R120G
the mutation abolishes the activities of isoform FPPS1; the mutation abolishes the activities of isoform FPPS2
R121G
the mutation abolishes the activities of isoform FPPS1; the mutation abolishes the activities of isoform FPPS2
K254A/K197G
the mutations result in a loss of enzyme activity and a lethal phenotype
K254E/K197G
the mutations result in a loss of enzyme activity and a lethal phenotype
S50L
-
mutant enzyme produces prenyl diphosphates with the same chain lengths as the wild-type enzyme does. 1.3-1.4fold decrease in ratio of Vmax to Km-value for dimethylallyl diphosphate and isopentenyl diphosphate
Y81D
-
contrary to wild-type, reaction of (Z)-ethynyldimethylallyl diphosphate plus isopentenyl diphosphate yields a mixture of products ethynylgeranyl, ethynylfarnesyl, and ethynylgeranylgeranyl diphosphates
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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