Information on EC 1.11.1.20 - prostamide/prostaglandin F2alpha synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.11.1.20
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RECOMMENDED NAME
GeneOntology No.
prostamide/prostaglandin F2alpha synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
thioredoxin + (5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate = thioredoxin disulfide + (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Arachidonic acid metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
thioredoxin:(5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate oxidoreductase
The enzyme contains a thioredoxin-type disulfide as a catalytic group. Prostamide H2 and prostaglandin H2 are the best substrates; the latter is converted to prostaglandin F2alpha. The enzyme also reduces tert-butyl hydroperoxide, cumene hydroperoxide and H2O2, but not prostaglandin D2 or prostaglandin E2.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
thioredoxin + (5Z)-N-(2-hydroxyethyl)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl]hept-5-enamide
thioredoxin disulfide + (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxy-N-(2-hydroxyethyl)prosta-5,13-dien-1-amide
show the reaction diagram
thioredoxin + (5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate
thioredoxin disulfide + (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoate
show the reaction diagram
thioredoxin + cumene hydroperoxide
thioredoxin disulfide + ?
show the reaction diagram
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?
thioredoxin + cumene hydroperoxide
thioredoxin disulfide + H2O + 2-phenylpropan-2-ol
show the reaction diagram
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?
thioredoxin + H2O2
thioredoxin disulfide + 2 H2O
show the reaction diagram
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?
thioredoxin + H2O2
thioredoxin disulfide + ?
show the reaction diagram
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?
thioredoxin + prostaglandin H2
thioredoxin disulfide + prostaglandin F2alpha
show the reaction diagram
thioredoxin + prostamide H2
thioredoxin disulfide + prostamide F2alpha
show the reaction diagram
thioredoxin + t-butyl hydroperoxide
thioredoxin disulfide + ?
show the reaction diagram
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?
thioredoxin + tert-butyl hydroperoxide
thioredoxin disulfide + H2O + tert-butanol
show the reaction diagram
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?
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
thioredoxin + (5Z)-N-(2-hydroxyethyl)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl]hept-5-enamide
thioredoxin disulfide + (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxy-N-(2-hydroxyethyl)prosta-5,13-dien-1-amide
show the reaction diagram
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(5Z)-N-(2-hydroxyethyl)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl]hept-5-enamide i.e. prostamide H2. The product of the reaction prostamide F2alpha is a COX-2-catalyzed metabolite of arachidonoyl ethanolamide that induces important pharmacological actions via interaction with a putative prostamide receptor
(5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxy-N-(2-hydroxyethyl)prosta-5,13-dien-1-amide i.e. prostamide F2alpha
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?
thioredoxin + (5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate
thioredoxin disulfide + (5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoate
show the reaction diagram
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(5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate i.e. prostaglandin H2. The product of the reaction prostaglandin F2alpha induces luteolysis in the estrous cycle and plays essential roles in parturition with its strong uterine contractile actions and has vasoconstriction and bronchoconstriction activities. PGF2alpha exerts these biological functions by binding to the FP receptor, a G-protein-coupled receptor that signals through Gq-mediated increases in intracellular calcium
(5Z,9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprosta-5,13-dienoate i.e. prostaglandin F2alpha
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?
thioredoxin + prostaglandin H2
thioredoxin disulfide + prostaglandin F2alpha
show the reaction diagram
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?
thioredoxin + prostamide H2
thioredoxin disulfide + prostamide F2alpha
show the reaction diagram
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
thioredoxin
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
(NH4)2SO4
1.5 M, stimulates about 4fold
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cumene hydroperoxide
competitive inhibition of prostamide F synthase activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(NH4)2SO4
stimulates
ammonium sulfate
the activity of the purified recombinant enzyme is stimulated about 4fold by 1.5 M ammonium sulfate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0076 - 0.014
(5Z)-N-(2-hydroxyethyl)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl]hept-5-enamide
0.0069 - 0.007
(5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate
0.026
cumene hydroperoxide
in 0.1 M KPB (pH 7.0), at 24C; pH 7.0, 24C
0.0069 - 1.6
H2O2
0.0076
prostamide H2
in 0.1 M KPB (pH 7.0), at 24C
0.4
t-butyl hydroperoxide
0.001
thioredoxin
pH 7.0, 24C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.09
(5Z)-N-(2-hydroxyethyl)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl]hept-5-enamide
Mus musculus
Q9DB60
pH 7.0, 24C, i.e. prostamide H2
0.25
(5Z,9alpha,11alpha,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate
Mus musculus
Q9DB60
pH 7.0, 24C, i.e. prostaglandin H2
0.1
cumene hydroperoxide
0.25
prostaglandin H2
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
0.09
prostamide H2
0.001
thioredoxin
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.9
cumene hydroperoxide
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
814
0.003
H2O2
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
22
35.85
prostaglandin H2
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
612
11.88
prostamide H2
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
7746
0.22
t-butyl hydroperoxide
Mus musculus
Q9DB60
in 0.1 M KPB (pH 7.0), at 24C
5218
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.053
prostamine F synthase activity, pH 7.0, 24C
0.062
prostaglandin F synthase activity, pH 7.0, 24C
0.25
prostamine F synthase activity, pH 7.0, 24C; substrate: tert-butyl hydroperoxide, pH 7.0, 24C
0.28
substrate: cumene hydroperoxide, pH 7.0, 24C; substrate: H2O2, pH 7.0, 24C
0.69
prostaglandin F synthase activity, pH 7.0, 24C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 8
pH 6.5: about 50% of maximal activity, pH 8.0: about 70% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
lowest activity in the cecum
Manually annotated by BRENDA team
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prostamide/PGF synthase is expressed preferentially in the white matter bundles of the entire central nervous system of adult mice with less marked expression in neuronal cell bodies
Manually annotated by BRENDA team
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
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the enzyme is colocalized with myelin basic protein in myelin sheaths but not in axons
Manually annotated by BRENDA team
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; cultured oligodendrocytes at 7 days in vitro express the enzyme in cytoplasmic processes where the enzyme is colocalized with myelin basic protein
Manually annotated by BRENDA team
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
; activity is the highest in spinal cord and brain followed by thymus, adrenal gland, heart, and genital organs
Manually annotated by BRENDA team
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there is a tendency for the white matter bundles in the spinal cord, medulla oblongata, pons, and cerebellar medulla to express prostamide/PGF synthase more strongly than those in other central nervous system regions
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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cultured oligodendrocytes at 7 days in vitro express the enzyme in cytoplasmic processes where the enzyme is colocalized with myelin basic protein
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20000
SDS-PAGE
21670
calculated from amino acid sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; Ni2+-agarose column chromatography and Q Sepharose column chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
construction of an expression plasmid using polyhistidine-tagged peptide-fused vector and mouse cDNA encoding a 201-amino acid polypeptide with molecular weight of 21669 Da and expression the protein in Escherichia coli; expressed in Escherichia coli BL21(DE3) cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the expression of prostamide/PGF synthase in myelin sheaths is age-dependent during the postnatal development, between postnatal days 9 and 14 the expression of the enzyme increases dramatically and preferentially in white matter bundles
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C44S
below 1% of wild-type activity; the mutant is almost inactive with less than 1% of wild type activity
C44S/C47S
below 1% of wild-type activity; the mutant is almost inactive with less than 1% of wild type activity
C47S
mutant shows reduced activity compared to the wild type enzyme; retains 63% of wild-type activity