Information on EC 2.5.1.39 - 4-hydroxybenzoate polyprenyltransferase

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

EC NUMBER
COMMENTARY hide
2.5.1.39
-
RECOMMENDED NAME
GeneOntology No.
4-hydroxybenzoate polyprenyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a polyprenyl diphosphate + 4-hydroxybenzoate = diphosphate + a 4-hydroxy-3-polyprenylbenzoate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alkenyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Metabolic pathways
-
-
plastoquinol-9 biosynthesis II
-
-
superpathway of ubiquinol-6 biosynthesis (eukaryotic)
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-
ubiquinol-10 biosynthesis (eukaryotic)
-
-
ubiquinol-10 biosynthesis (prokaryotic)
-
-
ubiquinol-6 biosynthesis from 4-hydroxybenzoate (eukaryotic)
-
-
ubiquinol-7 biosynthesis (eukaryotic)
-
-
ubiquinol-7 biosynthesis (prokaryotic)
-
-
ubiquinol-8 biosynthesis (eukaryotic)
-
-
ubiquinol-8 biosynthesis (prokaryotic)
-
-
ubiquinol-9 biosynthesis (eukaryotic)
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-
ubiquinol-9 biosynthesis (prokaryotic)
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-
Ubiquinone and other terpenoid-quinone biosynthesis
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-
ubiquinone biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
polyprenyl-diphosphate:4-hydroxybenzoate polyprenyltransferase
This enzyme, involved in the biosynthesis of ubiquinone, attaches a polyprenyl side chain to a 4-hydroxybenzoate ring, producing the first ubiquinone intermediate that is membrane bound. The number of isoprenoid subunits in the side chain varies in different species. The enzyme does not have any specificity concerning the length of the polyprenyl tail, and accepts tails of various lengths with similar efficiency [2,4,5].
CAS REGISTRY NUMBER
COMMENTARY hide
9030-77-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
guinea pig
-
-
Manually annotated by BRENDA team
gene COQ2
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
IAM 1219
-
-
Manually annotated by BRENDA team
strain SPQ-01
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
-
the enzyme catalyzes one of the first steps in ubiquinone or coenzyme Q, CoQ, biosynthesis
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
4-hydroxybenzoate + solanesyl-diphosphate
4-hydroxy-3-nonaprenylbenzoate + diphosphate
show the reaction diagram
-
i.e.all-trans nonaprenyl diphosphate
-
-
?
a polyprenyl diphosphate + 4-hydroxybenzoate
diphosphate + a 4-hydroxy-3-polyprenylbenzoate
show the reaction diagram
decaprenyl diphosphate + 4-hydroxybenzoate
diphosphate + decaprenyl-4-hydroxybenzoate
show the reaction diagram
farnesyl diphosphate + 4-hydroxybenzoate
3-farnesyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
-
-
-
-
?
farnesyl diphosphate + 4-hydroxybenzoate
farnesyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
geranyl diphosphate + 4-hydroxybenzoate
3-geranyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
geranyl diphosphate + 4-hydroxybenzoate
diphosphate + 3-geranyl-4-hydroxybenzoate
show the reaction diagram
geranylgeranyl diphosphate + 4-hydroxybenzoate
3-geranylgeranyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
-
-
-
-
?
geranylgeranyl diphosphate + 4-hydroxybenzoate
geranylgeranyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
hexaprenyl diphosphate + 4-hydroxybenzoate
hexaprenyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
-
at 68% of the activity with nonaprenyl diphosphate
-
-
?
octaprenyl diphosphate + 4-hydroxybenzoate
4-hydroxy-3-octaprenylbenzoate + diphosphate
show the reaction diagram
-
-
-
-
?
pentaprenyl diphosphate + 4-hydroxybenzoate
pentaprenyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
-
86% of the activity with nonaprenyl diphosphate
-
-
?
phytyl diphosphate + 4-hydroxybenzoate
phytyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
-
at 1% of the activity with nonaprenyl diphosphate
-
-
?
solanesyl diphosphate + 4-hydroxybenzoate
4-hydroxy-3-nonaprenylbenzoate
show the reaction diagram
solanesyl diphosphate + 4-hydroxybenzoate
diphosphate + 3-solanesyl-4-hydroxybenzoate
show the reaction diagram
solanesyl diphosphate + 4-hydroxybenzoate
diphosphate + nonaprenyl-4-hydroxybenzoate
show the reaction diagram
tetraprenyl diphosphate + 4-hydroxybenzoate
tetraprenyl-4-hydroxybenzoate + diphosphate
show the reaction diagram
-
6% of the activity with nonaprenyl 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
a polyprenyl diphosphate + 4-hydroxybenzoate
diphosphate + a 4-hydroxy-3-polyprenylbenzoate
show the reaction diagram
-
-
-
-
?
decaprenyl diphosphate + 4-hydroxybenzoate
diphosphate + decaprenyl-4-hydroxybenzoate
show the reaction diagram
solanesyl diphosphate + 4-hydroxybenzoate
diphosphate + 3-solanesyl-4-hydroxybenzoate
show the reaction diagram
solanesyl diphosphate + 4-hydroxybenzoate
diphosphate + nonaprenyl-4-hydroxybenzoate
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
strong inhibiting effect
Ni2+
-
partly effective for activity
Zn2+
-
strong inhibiting effect
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4-dinitrophenol
-
16% inhibition at 1 mM
4-Aminobenzoic acid
-
-
4-Chlorobenzoic acid
-
-
4-nitrobenzoate
acetyl-CoA
-
weak
Ag+
-
complete inhibition at 0.1 mM
bacitracin
-
strong inhibitor
beta-octyl glucoside
-
-
Brij W1
-
inhibition at 0.5% or more, activation at 0.05%
cis-vaccenic acid
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synonym: cis-11-octadecenoic acid
deoxycholate
-
complete inhibition at 0.5%
Diphenylamine
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-
Hg2+
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complete inhibition at 0.1 mM
iodoacetamide
-
-
isopentenyl diphosphate
-
-
N-ethylmaleimide
-
67% inhibition at 1 mM
NaCl
-
increasing concentrations in the presence of 5 mM Mg2+ result in inhibition
Ni2+
-
3.15% of activity remaining at 10 mM
Nonidet P-40
-
inhibition at 0.5% or more, activation at 0.05%
p-chloromercuribenzoate
palmitoyl-CoA
-
-
Sodium deoxycholate
Triton X-100
Tween 80
additional information
-
no inhibitor: taurodeoxycholate
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3-[(cholamidopropyl)dimethylammonio]-1-propanesulfonate
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0.05% final concentration, significant stimulation of activity
Brij W1
cardiolipin
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-
CHAPS
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46% increase at 0.01%
dipalmitoylphosphatidylcholine
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-
Nonidet P-40
phosphatidylethanolamine
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-
phosphatidylglycerol
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Phospholipid
sodium cholate
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0.05% final concentration, significant stimulation of activity
Sodium deoxycholate
Triton X-100
Tween 80
additional information
-
not stimulated by sodium deoxycholate, lysophosphatidyl choline, or octylglucoside
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00114 - 0.054
4-hydroxybenzoate
0.022
farnesyl diphosphate
-
pH 7.8, 37°C
0.0597
geranyl diphosphate
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-
0.254
geranylgeranyl diphosphate
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pH 7.8, 37°C
0.000833 - 0.14
nonaprenyl diphosphate
0.031
solanesyl diphosphate
-
pH 7.8, 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0006
-
in the presence of 5 mM Co2+
0.0013
-
in the presence of 5 mM Mn2+
0.014
-
in the presence of 5 mM Mg2+
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
8 - 9
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mitochondria
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7 - 9.4
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50% activity at pH 6.7 and pH 9.4
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high enzyme expression
Manually annotated by BRENDA team
with developing embryo
Manually annotated by BRENDA team
low expression level
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
low expression level
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
low activity
Manually annotated by BRENDA team
-
low activity
Manually annotated by BRENDA team
-
Golgi III vesicles, high specific activity, associated with inner luminal surface of microsomal vesicles
-
Manually annotated by BRENDA team
additional information
-
at low levels: rough and smooth I microsomes, mitochondria, not: peroxisomes, cytosol
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000
-
SDS-PAGE
32510
-
precited from cDNA
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 32000, SDS-PAGE
additional information
-
the enzyme contains 6 transmembrane sequences and an UbiA domain
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structures of the enzyme in its apo and substrate-bound states at 3.3 and 3.6 A resolution, respectively
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
isolated mitochondria can be stored frozen for 2-3 weeks prior to preparation of membrane fragments without any loss of activity, preparation of mitochondrial fragments loses activity after 2 cycles of freezing and thawing
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, activity is maintained for several months
-25°C, stable for several months, loss of 20% activity after one year
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cloned under control of different promoters, expressed in Nicotiana tabacum
-
expressed in Escherichia coli
-
expressed in Saccharomyces cerevisiae
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gene cluster consisting of ubiC gene and a portion of ubiA is cloned and expressed in Escherichia coli
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gene COQ2, complementation of yeast Coq2 null mutant cells
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gene COQ2, DNA and amino acid sequence determination and analysis, functional expression in and complementation of yeast Coq2 null mutant cells, CoQ biosynthesis rate is lower in the yeast cells when rescued with the human enzyme compared to cells rescued with the yeast enzyme
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gene COQ2, DNA and amino acid sequence determination and analysis, genotyping
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gene PPT1, DNA and amino acid sequence determination and analysis, functional expression in and complementation of Saccharomyces cerevisiae and Schizosaccharomyces pombe enzyme null mutant cells, expression as GFP-fusion protein in Arabidopsis plants
overexpressed in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
study of the expression of ubiA using an ubiA-lacZ fusion system shows that the ubiA expression is catabolite-repressed by glucose
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D191A
-
mutant shows no 3-geranylgeranyl-4-hydroxybenzoate formation, mutant shows some residual hydrolysis activity
D195A
-
mutant shows no 3-geranylgeranyl-4-hydroxybenzoate formation, mutant shows some residual hydrolysis activity
D71A
-
mutant shows no 3-geranylgeranyl-4-hydroxybenzoate formation, mutant shows some residual hydrolysis activity
D75A
-
mutant shows no 3-geranylgeranyl-4-hydroxybenzoate formation, mutant shows some residual hydrolysis activity
R137A
-
mutant shows a strongly reduced formation of 3-geranylgeranyl-4-hydroxybenzoate, mutant shows some residual hydrolysis activity
R197H/N228S
-
naturally occurring lethal enzyme mutation, renal phenotype including collapsing glomerulonepritis and steroid-resistant nephrotic syndome
S109N
-
naturally occurring lethal mutation causing a severe phenotype, CoQ10 synthesis is significantly decreased in cultured skin fibroblasts, a kidney sample reveals focal segmental glomerulosclerosis lesions, The affected glomeruli demonstrate mesangial hypercellularity, segmental sclerosis of glomerular capillaries, enlarged podocytes with intracytoplasmic hyaline vacuoles and adhesions to the Bowman's capsule, podocytes are enlarged and show extensive foot process effacement, overview
S146N
-
naturally occurring lethal enzyme mutation, the mutation causes oliguria, oligohydramnios, hypertension, and seizures
Y297C
-
naturally occurring lethal enzyme mutation causing a severe phenotype, with end-stage renal failure, focal segmental glomeruloslerosis, steroid-resistant nephrotic syndome, developmental delay and developmental regression, optic atrophy, seizures, myoclonic seizures, refractory seizures, status epilepticus, and nystagmoid movements, overview
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
-
in patients with encephalomyopathy, nephropathy and severe CoQ10 deficiency, a homozygous mutation was identified in the CoQ10 biosynthesis gene COQ2. mRNA levels of this gene are significantly increased in patients fibroblast, and its activity is significantly lower in fibroblasts of patients with mutation c.890A.G relative to controls and CoQ10-deficient fibroblasts from ataxic patient
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