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Information on EC 2.5.1.90 - all-trans-octaprenyl-diphosphate synthase
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EC Tree
2.5.1.90 all-trans-octaprenyl-diphosphate synthaseIUBMB Comments
This enzyme catalyses the condensation reactions resulting in the formation of all-trans-octaprenyl diphosphate, the isoprenoid side chain of ubiquinone-8 and menaquinone-8. The enzyme adds five isopentenyl diphosphate molecules sequentially to farnesyl diphosphate with trans stereochemistry
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Word Map
- 2.5.1.90
- ubiquinone
-
isoprenoids
-
polyprenyl
-
decaprenylation
- menaquinone
-
prenylates
- undecaprenyl
-
geranyl
- isoprene
-
hexaprenyl
-
farnesyl-pp
-
solanesyl
-
chain-length
-
ddxxd
- 4-hydroxybenzoate
- dolichols
- coq
-
polyisoprenoids
-
dimethylallyl
-
carbocation
- cis-prenyltransferase
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Reaction Schemes
Synonyms
trans-prenyltransferase, octaprenyl diphosphate synthase, octaprenyl pyrophosphate synthase, octaprenyl pyrophosphate, opp synthetase, gbs1789, octaprenyl-diphosphate synthase, long-chain trans-prenyltransferase, long-chain c40 octaprenyl diphosphate synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
gbs1789
IspB
octaprenyl diphosphate synthase
octaprenyl pyrophosphate synthase
OPPs
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate
sequential mechanism
-
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate
isopentenyl diphosphate condensation rather than product release is rate limiting
-
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 5 isopentenyl units)
This enzyme catalyses the condensation reactions resulting in the formation of all-trans-octaprenyl diphosphate, the isoprenoid side chain of ubiquinone-8 and menaquinone-8. The enzyme adds five isopentenyl diphosphate molecules sequentially to farnesyl diphosphate with trans stereochemistry
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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)-8-O-(N-methyl-2-aminobenzoyl)-3,7-dimethyl-2,6-octandien-1-diphosphate + 5 isopentenyl diphosphate
?
-
-
-
?
(2E,6E)-farnesyl diphosphate + 3-bromo-3-butenyl diphosphate
diphosphate + ?
-
isopentenyl diphosphate analogue, showing a significantly reduced activity. Only two 3-bromo-3-butenyl diphosphate condensation reactions occurr in 24 h and the reaction products do not reach C40 and C55. Use results in trapping of farnesol in the reaction from radioloabeled farnesyl diphosphate under basic conditions, consistent with a sequential mechanism
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + all-trans-nonaprenyl diphosphate
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + octaprenyl diphosphate + nonaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
80% all-trans-octaprenyl diphosphate, 20% nonaprenyl diphosphate in presence of 0.01 mM enzyme, 0.0001 mM farnesyl diphosphate, 0.001 mM isopentenyl diphosphate. Variation of concentrations and conditions allows for synthesis of products with chain length C20 to C60
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the enzyme catalyzes the successive condensation of farnesyl diphosphate with five isopentenyl pyrophosphate molecules to form trans-C40-octaprenyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
(2E,6E)-farnesyl diphosphate is the most effective substrate
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
(2E,6E)-farnesyl diphosphate is the most effective substrate
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
the product of chain elongation is C40 and the rate of its conversion to C45 is negligible. Under single-turnover condition with 0.01 mM enzyme-farnesyl diphosphate complex and 0.001 mM isopentenyl diphosphate, only the C20 is formed
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the polymer all-trans C40-octaprenyl pyrophosphate forms the side chain of ubiquinone that is involved in electron transport system to produce ATP
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the product of chain elongation catalyzed by the Thermotoga maritima enzyme is C40 and the rate of its conversion to C45 is negligible. Under single-turnover condition with 0.01 mM octaprenyl pyrophosphate synthase/farnesyl pyrophosphate complex and 0.001 mM isopentenyl pyrophosphate, only the C20 is formed
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the polymer all-trans C40-octaprenyl pyrophosphate forms the side chain of ubiquinone that is involved in electron transport system to produce ATP
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the product of chain elongation catalyzed by the Thermotoga maritima enzyme is C40 and the rate of its conversion to C45 is negligible. Under single-turnover condition with 0.01 mM octaprenyl pyrophosphate synthase/farnesyl pyrophosphate complex and 0.001 mM isopentenyl pyrophosphate, only the C20 is formed
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + octaprenyl diphosphate + nonaprenyl diphosphate
0.7% activity compared to (2E,6E)-farnesyl diphosphate
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + octaprenyl diphosphate + nonaprenyl diphosphate
0.7% activity compared to (2E,6E)-farnesyl diphosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
?
5.3% activity compared to (2E,6E)-farnesyl diphosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
?
5.3% activity compared to (2E,6E)-farnesyl diphosphate
-
-
?
geranylgeranyl diphosphate + isopentenyl diphosphate
?
53.4% activity compared to (2E,6E)-farnesyl diphosphate
-
-
?
geranylgeranyl diphosphate + isopentenyl diphosphate
?
53.4% activity compared to (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
at the bottom of the active-site tunnel, residues M123 and M135 act in concert to form a wall which determines the final chain length, substrate binding and enzyme-ligand structure analysis, overview
-
-
?
additional information
?
-
-
at the bottom of the active-site tunnel, residues M123 and M135 act in concert to form a wall which determines the final chain length, substrate binding and enzyme-ligand structure analysis, overview
-
-
?
additional information
?
-
no substrate: dimethylallyl diphosphate, geranyl diphosphate
-
-
?
additional information
?
-
residues Tyr-38, Lys-235, and Arg-321 are involved in chain length determination
-
-
?
additional information
?
-
no substrate: geranyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
no substrate: geranyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
the isopentenyl diphosphate condensation represents the rate-limiting step of the reaction
-
-
?
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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
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the enzyme catalyzes the successive condensation of farnesyl diphosphate with five isopentenyl pyrophosphate molecules to form trans-C40-octaprenyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the polymer all-trans C40-octaprenyl pyrophosphate forms the side chain of ubiquinone that is involved in electron transport system to produce ATP
-
-
?
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate
5 diphosphate + all-trans-octaprenyl diphosphate
the polymer all-trans C40-octaprenyl pyrophosphate forms the side chain of ubiquinone that is involved in electron transport system to produce ATP
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Triton X-100
addition of 0.1% and 0.5% Triton X-100 activates the enzyme by 3.9- and 4.7fold, respectively
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
African Swine Fever
The African swine fever virus prenyltransferase is an integral membrane trans-geranylgeranyl-diphosphate synthase.
Melanoma
Gene Expression Profiles of Adult Peripheral and Cord Blood Mononuclear Cells Altered by Lipopolysaccharide.
Neoplasms
Gene Expression Profiles of Adult Peripheral and Cord Blood Mononuclear Cells Altered by Lipopolysaccharide.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0008
(2E,6E)-8-O-(N-methyl-2-aminobenzoyl)-3,7-dimethyl-2,6-octandien-1-diphosphate
at pH 7.5, temperature not specified in the publication
0.0015
(2E,6E)-farnesyl diphosphate
at pH 7.5, temperature not specified in the publication
0.004
isopentenyl diphosphate
with (2R,6E)-farnesyl diphosphate as cosubstrate, at pH 7.5, temperature not specified in the publication
0.0069
isopentenyl diphosphate
with (2E,6E)-8-O-(N-methyl-2-aminobenzoyl)-3,7-dimethyl-2,6-octandien-1-diphosphate as cosubstrate, at pH 7.5, temperature not specified in the publication
0.34
isopentenyl diphosphate
with dimethylallyl diphosphate as cosubstrate, at pH 7.5 and 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.055
(2E,6E)-8-O-(N-methyl-2-aminobenzoyl)-3,7-dimethyl-2,6-octandien-1-diphosphate
at pH 7.5, temperature not specified in the publication
0.00000023
(2E,6E)-farnesyl diphosphate
mutant A76Y/S77F, pH 7.5, 25°C
0.06
(2E,6E)-farnesyl diphosphate
at pH 7.5, temperature not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
31000
with geranylgeranyl diphosphate as substrate, at pH 7.5 and 30°C
58000
with (2E,6E)-farnesyl diphosphate as substrate, at pH 7.5 and 30°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25 - 85
the enzyme activity at temperatures ranging from 25°C to 85°C exponentially increases with elevated temperature
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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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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
-
it is impossible to obtain an ispB deletion mutant unless the ispB gene or its homolog is supplied on a plasmid. The ispB gene is essential for the normal growth of Escherichia coli
metabolism
physiological function
additional information
evolution
octaprenyl diphosphate synthase, OPP, belongs to the trans-prenyltransferase class of protein
metabolism
octaprenyl pyrophosphate synthase catalyzes the chain elongation of farnesyl pyrophosphate via consecutive condensation reactions with five molecules of isopentenyl pyrophosphate to generate all-trans C40-octaprenyl pyrophosphate. The polymer forms the side chain of ubiquinone that is involved in electron transport system to produce ATP
metabolism
-
octaprenyl pyrophosphate synthase catalyzes the chain elongation of farnesyl pyrophosphate via consecutive condensation reactions with five molecules of isopentenyl pyrophosphate to generate all-trans C40-octaprenyl pyrophosphate. The polymer forms the side chain of ubiquinone that is involved in electron transport system to produce ATP
-
physiological function
-
octaprenyl diphosphate synthase is responsible for the synthesis of the side chain of isoprenoid quinones
physiological function
the enzyme catalyzes consecutive condensation reactions of farnesyl diphosphate with isopentenyl diphosphate to generate octaprenyl diphosphate, which constitutes the side chain of bacterial ubiquinone or menaquinone
physiological function
the chromosomal ispB disrupted mutant cannot be isolated unless the ispB gene or its homolog is supplied on a plasmid. The chromosomal ispB disruptants that harbor plasmids carrying the ispB homologs from Haemophilus influenzae and Synechocystis sp. strain PCC6803 produce mainly ubiquinone 7 and ubiquinone 9, respectively
physiological function
gene product of gbs1789 is involved in the biosynthesis of long-chain demethylmenaquinones. A gbs1789 mutant cannot respire in the presence of heme and dihydroxy-2-naphthoic acid. Isoprenoid side chains from Group B Streptococcus demethylmenaquinones are produced by the protein encoded by the gbs1783 gene, since this gene can complement an Escherichia coli ispB mutant defective for isoprenoids chain synthesis
physiological function
the enzyme catalyzes consecutive condensation reactions of one allylic substrate farnesyl diphosphate and five homoallylic substrate isopentenyl diphosphate molecules to form a C40 long-chain product octaprenyl diphosphate, which serves as a side chain of ubiquinone and menaquinone
physiological function
the enzyme is essential for the biosynthesis of bacterial ubiquinone or menaquinone side chains, which play an important role in the electron-transport system
physiological function
Streptococcus agalactiae serogroup III NEM316
-
gene product of gbs1789 is involved in the biosynthesis of long-chain demethylmenaquinones. A gbs1789 mutant cannot respire in the presence of heme and dihydroxy-2-naphthoic acid. Isoprenoid side chains from Group B Streptococcus demethylmenaquinones are produced by the protein encoded by the gbs1783 gene, since this gene can complement an Escherichia coli ispB mutant defective for isoprenoids chain synthesis
-
additional information
enzyme homology modeling, overview. (2E,6E)-Farnesyl diphosphate is bound to the first DDXXD motif, and isopentenyl diphosphate is bound to several cationic residues (e.g. Arg, Lys, and His) via diphosphate, but not to the second DDXXD motif. The enzyme contains an elongated tunnel-shaped crevice as the active site to accommodate its reactants and product
additional information
-
enzyme homology modeling, overview. (2E,6E)-Farnesyl diphosphate is bound to the first DDXXD motif, and isopentenyl diphosphate is bound to several cationic residues (e.g. Arg, Lys, and His) via diphosphate, but not to the second DDXXD motif. The enzyme contains an elongated tunnel-shaped crevice as the active site to accommodate its reactants and product
additional information
enzyme structure modelling using the structure of Rhodobacter capsulatus decaprenyl diphosphate synthase, PDB ID 3mzv, as a template model
additional information
-
enzyme structure modelling using the structure of Rhodobacter capsulatus decaprenyl diphosphate synthase, PDB ID 3mzv, as a template model
Show AA Sequence and Transmembrane Helices (3381 entries)
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PDB
SCOP
CATH
UNIPROT
ORGANISM