Information on EC 2.5.1.85 - all-trans-nonaprenyl diphosphate synthase [geranylgeranyl-diphosphate specific]

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.5.1.85
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RECOMMENDED NAME
GeneOntology No.
all-trans-nonaprenyl diphosphate synthase [geranylgeranyl-diphosphate specific]
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranylgeranyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
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nonaprenyl diphosphate biosynthesis II
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Terpenoid backbone biosynthesis
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isoprenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranylgeranyl-diphosphate:isopentenyl-diphosphate transtransferase (adding 5 isopentenyl units)
Geranylgeranyl diphosphate is preferred over farnesyl diphosphate as allylic substrate [1]. The plant Arabidopsis thaliana has two different enzymes that catalyse this reaction. SPS1 contributes to the biosynthesis of the ubiquinone side-chain while SPS2 supplies the precursor of the plastoquinone side-chains [2].
CAS REGISTRY NUMBER
COMMENTARY hide
83745-07-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
gene SlSPS
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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co-expression network of the Arabidopsis thaliana solanesyl-diphosphate synthase family; co-expression network of the Arabidopsis thaliana solanesyl-diphosphate synthase family
malfunction
metabolism
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
(2E,6E)-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
(2E,6E)-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + nonaprenyl diphosphate
show the reaction diagram
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17% of the activity with geranylgeranyl diphosphate
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-
?
dimethylallyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
low activity
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-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
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
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
optimal level of activity obtained at 0.5-1 mM. No activation by Mn2+
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-[(n-oct-1-ylamino)ethyl] 1,1-bisphosphonic acid
strong enzyme inhibitor
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
fibrillin 5B
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FBN5-B, fibrillin 5B specifically interacts with solanesyl diphosphate synthase 1, which biosynthesize the solanesyl moiety of plastoquinone-9. Plants containing defective FBN5-B accumulate less plastoquinone-9 and its cyclized product, plastochromanol-8, but the levels of tocopherols are not affected. Homozygous mutations in FBN5 are seedling-lethal. FBN5-B is required for PQ-9 biosynthesis through its interaction with enzyme SPS. FBN5 binding to the hydrophobic solanesyl moiety, which is generated by SPS1, in FBN5 B/SPS homodimeric complexes stimulates the enzyme activity of SPS1; FBN5-B, fibrillin 5B specifically interacts with solanesyl diphosphate synthase 2, which biosynthesize the solanesyl moiety of plastoquinone-9. Plants containing defective FBN5-B accumulate less plastoquinone-9 and its cyclized product, plastochromanol-8, but the levels of tocopherols are not affected. Homozygous mutations in FBN5 are seedling-lethal. FBN5-B is required for PQ-9 biosynthesis through its interaction with enzyme SPS. FBN5 binding to the hydrophobic solanesyl moiety, which is generated by SPS2, in FBN5 B/SPS homodimeric complexes stimulates the enzyme activity of SPS2
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00689 - 5.73
(2E,6E)-farnesyl diphosphate
0.00459 - 0.00512
farnesyl diphosphate
0.0548
geranyl diphosphate
pH 7.4, 37C
0.000565 - 1.61
geranylgeranyl diphosphate
0.0192 - 151
isopentenyl diphosphate
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.032 - 3.77
(2E,6E)-farnesyl diphosphate
29.7
farnesyl diphosphate
Arabidopsis thaliana
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pH 8.0, 30C
0.065
geranyl diphosphate
Trypanosoma cruzi
Q964Q8
pH 7.4, 37C
0.087 - 21
geranylgeranyl diphosphate
0.043 - 15
isopentenyl diphosphate
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00701 - 547
(2E,6E)-farnesyl diphosphate
81
0.00119
geranyl diphosphate
Trypanosoma cruzi
Q964Q8
pH 7.4, 37C
175
0.012 - 2770
geranylgeranyl diphosphate
231
0.0014 - 595
isopentenyl diphosphate
113
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.01
calculated from sequence
6.12
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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high activity
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
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solanesyl diphosphate synthase is targeted to the plastid and both solanesol and plastoquinone are associated with thylakoid membranes
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
39000
x * 39000, calculated from sequence
39200
x * 39200, calculated
46044
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x * 46044, calculated from sequence
46600
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2 * 46600, His6-tagged protein, calculated from sequence
60000
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x * 60000, His-tagged fusion protein, SDS-PAGE
108000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 46600, His6-tagged protein, calculated from sequence
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40
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pH 8.0, 10 minm, stable below
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His6-tagged At-SPS2 fusion protein partially purified to about 10% purity, truncated from of At-SPS2 (At-SPS2DELTA, in which the 30 N-terminal residues of the putative signal-peptide are removed and, instead the His6 tag is attached to the N-terminus) is purified to about 90% purity
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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expression in Escherichia coli, His6-tagged At-SPS2 fusion protein and the truncated from of At-SPS2 (At-SPS2DELTA, in which the 30 N-terminal residues of the putative signal-peptide are removed and, instead the His6 tag is attached to the N-terminus)
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expression of TcSPPS is able to complement an Escherichia coli ispB mutant
gene AtSPS1, overexpressing of the plastoquinone-9 biosynthesis gene SPS1 in Arabidopsis thaliana generating plants that specifically accumulate plastoquinone-9 and its derivative plastochromanol-8
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gene AtSPS1, phylogenetic analysis, recombinant expression of N-terminally GST-tagged enzyme in Nicotiana benthamiana epidermis cell endoplasmic reticulum using Agrobacterium tumefaciens strain C58C1 for transfection; gene AtSPS2, phylogenetic analysis, recombinant expression of N-terminally GST-tagged enzyme in Nicotiana benthamiana leaf chloroplasts using Agrobacterium tumefaciens strain C58C1 for transfection
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gene SlSPS, constitutive overexpression of SlSPS in immature tobacco leaves elevates the plastoquinone content in the leaves
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gene SlSPS, recombinant expression in Escherichia coli. In planta, constitutive overexpression of SlSPS elevates the plastoquinone content of immature tobacco leaves
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heterologous expression of either SPS1 allows the generation of UQ-9 in a decaprenyl diphosphate synthase-defective strain of fission yeast and also in wild-type Escherichia coli; heterologous expression of SPS1 allows the generation of UQ-9 in a decaprenyl diphosphate synthase-defective strain of fission yeast and also in wild-type Escherichia coli
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heterologously expressed in Escherichia coli as as His6-tagged fusion protein
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information