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Information on EC 2.5.1.84 - all-trans-nonaprenyl diphosphate synthase [geranyl-diphosphate specific]
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2.5.1.84 all-trans-nonaprenyl diphosphate synthase [geranyl-diphosphate specific]IUBMB Comments
(2E,6E)-Farnesyl diphosphate and geranylgeranyl diphosphate are less effective as substrates than geranyl diphosphate. The enzyme is involved in the synthesis of the side chain of menaquinone-9 . In Oryza sativa the enzyme SPS2 is involved in providing solanesyl diphosphate for plastoquinone-9 formation .
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Word Map
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
Synonyms
all-trans-nonaprenyl-diphosphate synthase [geranyl-diphosphate specific], nonaprenyl diphosphate synthase, nonaprenylpyrophosphate synthetase, OsSPS1, OsSPS2, solanesyl diphosphate synthase, solanesyl-diphosphate synthase, SolPP synthase, SPP synthase, SPP-synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
all-trans-nonaprenyl-diphosphate synthase [geranyl-diphosphate specific]
-
-
-
-
OsSPS2
solanesyl diphosphate synthase
SPP synthase
Sps2
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + 7 isopentenyl diphosphate = 7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate:isopentenyl-diphosphate transtransferase (adding 7 isopentenyl units)
(2E,6E)-Farnesyl diphosphate and geranylgeranyl diphosphate are less effective as substrates than geranyl diphosphate. The enzyme is involved in the synthesis of the side chain of menaquinone-9 [1]. In Oryza sativa the enzyme SPS2 is involved in providing solanesyl diphosphate for plastoquinone-9 formation [3].
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CAS REGISTRY NUMBER
COMMENTARY
83745-07-7
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
44% of the rate with geranyl diphosphate
products range from C 15 to C45
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
all-trans-farnesyl methylenediphosphonate + isopentenyl diphosphate
?
-
-
-
-
?
dimethylallyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + nonaprenyl diphosphate
18.1% of the activity with geranyl diphosphate, OsSPS2
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + ?
18% of the rate with geranyl diphosphate
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + nonaprenyl diphosphate
geranyl diphosphate is the preferred substrate, OsSPS2
-
-
?
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + nonaprenyl diphosphate
34.6% of the activity with geranyl diphosphate, OsSPS2
-
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
all-trans-nonaprenyl diphosphate is the major product
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
the concentration of the complex between farnesyl diphosphate and Mg2+, the priming substrate for this synthase, does not affect the product distribution, provided that the concentration of isopentenyl diphosphate/Mg2+ is maintained at a certain level. The level of isopentenyl diphosphate/Mg2+ is decisive in affecting the chain length distribution of the products of the prenyltransferase reaction
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
with MgCl2 nonaprenyl diphosphate is the longest product, with MnCl2 or CoCl2, the longest products are C50 and C55, respectively, partially purified enzyme
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
activity with farnesyl diphosphate is lower than with geranyl diphosphate
-
-
?
all-trans-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
about 10% of the activity with geranyl diphosphate
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
variable product specificity depending on Mg2+ concentration. all-trans-Nonaprenyl diphosphate is the longest product
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
farnesyl diphosphate is the preferred acceptor substrate
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + nonaprenyl diphosphate
OsSP2 is involved in the supply of all-trans-nonaprenyl diphosphate for plastoquinone-9 biosynthesis
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + nonaprenyl diphosphate
44% of the activity with geranyl diphosphate, OsSPS2
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
the chain length of the synthesized polyprenyl diphosphate is dependent on the concentration of Mg2+ in the medium. At 0.1 mM Mg2+, C25, C30 and C35 compounds are produced with C25 predominating. At 0.5 mM Mg2+, C25, C30, C35 and C40 compounds are produced with C35 and C40 predominating. At 20 mM Mg2+, C40 and C45 are produced without accumulation od shorter compounds
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
variable product specificity depending on Mg2+ concentration. all-trans-Nonaprenyl diphosphate is the longest product
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
the enzyme is involved in the synthesis of the side chain of menaquinone-9
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
geranyl diphosphate is the preferred substrate
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
best substrate
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
geranyl diphosphate is the preferred acceptor substrate
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
-
?
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
-
?
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
-
activity with geranylgeranyl diphosphate is lower than with geranyl diphosphate
-
-
?
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
35% of the rate with farnesyl diphosphate
products range from C 15 to C45
-
?
geranylgeranyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-nonaprenyl diphosphate
-
about 25% of the activity with geranyl diphosphate
-
-
?
additional information
?
-
-
no activity with geranyl phosphate or dimethylallyl phosphate
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-
?
additional information
?
-
-
no activity with geranylneryl diphosphate or dimethylallyl diphosphate
-
-
?
additional information
?
-
-
no activity with geranylneryl diphosphate or dimethylallyl diphosphate
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + nonaprenyl diphosphate
OsSP2 is involved in the supply of all-trans-nonaprenyl diphosphate for plastoquinone-9 biosynthesis
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
the enzyme is involved in the synthesis of the side chain of menaquinone-9
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
geranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
-
with MgCl2 nonaprenyl diphosphate is the longest product, with MnCl2 or CoCl2, the longest products are C50 and C55, respectively, partially purified enzyme
Mg2+
Mn2+
Mg2+
-
enzyme requires Mg2+, variable product specificity depending on Mg2+ concentration
Mg2+
-
Mg2+ is absolutely required for activity, Mn2+ is less effective. The chain length of the synthesized polyprenyl diphosphate is dependent on the concentration of Mg2+ in the medium. At 0.1 mM Mg2+, C25, C30 and C35 compounds are produced with C25 predominating. At 0.5 mM Mg2+, C25, C30, C35 and C40 compounds are produced with C35 and c40 predominating. At 20 mM Mg2+, C40 and C45 are produced without accumulation od shorter compounds
Mg2+
-
the concentration of the complex between farnesyl diphosphate and Mg2+, the priming substrate for this synthase, does not affect the product distribution, provided that the concentration of isopentenyl diphosphate/Mg2+ is maintained at a certain level. The level of isopentenyl diphosphate/Mg2+ is decisive in affecting the chain length distribution of the products of the prenyltransferase reaction
Mg2+
-
with MgCl2 nonaprenyl diphosphate is the longest product, with MnCl2 or CoCl2, the longest products are C50 and C55, respectively, partially purified enzyme
Mg2+
-
no activity in absence of divalent metal ion, activation with 2 mM Mg2+ is 50% of that obtained with Mn2+
Mn2+
-
with MgCl2 nonaprenyl diphosphate is the longest product, with MnCl2 or CoCl2, the longest products are C50 and C55, respectively, partially purified enzyme
Mn2+
-
no activity in absence of divalent metal ion, 0.1 mM Mn2+ is required for optimal activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00076
all-trans-farnesyl diphosphate
-
pH 7.7, 37°C, in absence of high molecular mass fraction
0.00075
all-trans-farnesyl diphosphate
-
pH 7.7, 37°C, in presence of high molecular mass faction
0.023
isopentenyl diphosphate
-
pH 7.7, 37°C, in absence of high molecular mass fraction
0.017
isopentenyl diphosphate
-
pH 7.7, 37°C, in presence of high molecular mass faction
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7 - 9.5
-
pH 7.0: about 60% of maximal activity, pH 9.5: about 60% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
isoform SPS2 shows a putative transit peptide of 57 amino acids for plastidal localization at the N-terminus
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
isoform SPS2 weakly complements the yeast coq1 disruptant, which does not form ubiquinone. Transformants produce ubiquinone 9 instead of the native yeast product ubiquinone 6. SPS2 is involved in providing solanesyl diphosphate for plastochinone-9 formation
metabolism
metabolism
solanesyl diphosphate is a precursor for solanesol biosynthesis. In the solanesol biosynthetic pathway, isopentenyl diphosphate is first isomerised to form dimethylallyl diphosphate by isopentenyl diphosphate isomerase, Ipi, which then binds to isopentenyl diphosphates one by one in the head-tail mode
metabolism
solanesyl diphosphate is a precursor for solanesol biosynthesis. In the solanesol biosynthetic pathway, isopentenyl diphosphate is first isomerised to form dimethylallyl diphosphate diphsphate by isopentenyl diphosphate isomerase, Ipi, which then binds to isopentenyl diphosphates one by one in the head-tail mode
metabolism
the enzyme interacts with the plastid lipid binding protein fibrillin5 for synthesis of the solanesyl diphosphate tail in plastoquinone-9
Show AA Sequence and Transmembrane Helices (320 entries)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
proteolytic modification
isoform SPS2 shows a putative transit peptide of 57 amino acids for plastidal localization at the N-terminus
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Fujii, H.; Sagami, H.; Koyama, T.; Ogura, K.; Seto, S.
Variable product specificity of solanesyl pyrophosphate synthetase
Biochem. Biophys. Res. Commun.
96
1648-1653
1980
Micrococcus luteus
brenda
Sagami, H.; Ogura, K.; Seto, S.
Solanesyl pyrophosphate synthetase from Micrococcus lysodeikticus
Biochemistry
16
4616-4622
1977
Micrococcus luteus
brenda
Sagami, H.; Ogura, K.
Nonaprenylpyrophosphate synthetase from Micrococcus luteus
Methods Enzymol.
110
206-209
1985
Micrococcus luteus
brenda
Ohnuma, S.i.; Koyama, T.; Ogura, K.
Alteration of the product specificities of prenyltransferases by metal ions
Biochem. Biophys. Res. Commun.
192
407-412
1993
Micrococcus luteus
brenda
Ohnuma, S.i.; Koyama, T.; Ogura, K.
Chain length distribution of the products formed in solanesyl diphosphate synthase reaction
J. Biochem.
112
743-749
1992
Micrococcus luteus
brenda
Ohnuma, S.i.; Koyama, T.; Ogura, K.
Purification of solanesyl-diphosphate synthase from Micrococcus luteus. A new class of prenyltransferase
J. Biol. Chem.
266
23706-23713
1991
Micrococcus luteus
brenda
Gotoh, T.; Koyama, T.; Ogura, K.
Farnesyl diphosphate synthase and solanesyl diphosphate synthase reactions of diphosphate-modified allylic analogs: the significance of the diphosphate linkage involved in the allylic substrates for prenyltransferase
J. Biochem.
112
20-27
1992
Micrococcus luteus
brenda
Teclebrhan, H.; Olsson, J.; Swiezewska, E.; Dallner, G.
Biosynthesis of the side chain of ubiquinone:trans-prenyltransferase in rat liver microsomes
J. Biol. Chem.
268
23081-23086
1993
Rattus norvegicus
brenda
Ohara, K.; Sasaki, K.; Yazaki, K.
Two solanesyl diphosphate synthases with different subcellular localizations and their respective physiological roles in Oryza sativa
J. Exp. Bot.
61
2683-2692
2010
Oryza sativa, Oryza sativa (Q75HZ9)
brenda
Yan, N.; Liu, Y.; Gong, D.; Du, Y.; Zhang, H.; Zhang, Z.
Solanesol: a review of its resources, derivatives, bioactivities, medicinal applications, and biosynthesis
Phytochem. Rev.
14
403-417
2015
Oryza sativa (Q653T6), Oryza sativa (Q75HZ9)
-
brenda
Kim, E.H.; Lee, D.W.; Lee, K.R.; Jung, S.J.; Jeon, J.S.; Kim, H.U.
Conserved function of fibrillin5 in the plastoquinone-9 biosynthetic pathway in Arabidopsis and rice
Front. Plant Sci.
8
1197
2017
Oryza sativa (Q75HZ9), Oryza sativa
brenda
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