Information on EC 1.97.1.2 - pyrogallol hydroxytransferase

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The expected taxonomic range for this enzyme is: Pelobacter

EC NUMBER
COMMENTARY
1.97.1.2
-
RECOMMENDED NAME
GeneOntology No.
pyrogallol hydroxytransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
a mechanism is proposed which combines an oxidative hydroxylation with a reductive dehydroxylation via molybdenum cofactor
-
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
transfer of the hydroxy group occurs via 2,4,3’,4’,5’-hexahydroxydiphenyl ether as an intermediate. The 1-OH group of pyrogallol coordinates to the MoVI atom of Moco and is oxidized to the orthoquinone form, while H144 accepts the phenolic proton. the 2-OH group of 1,2,3,5-tetrahydroxybenzene adds to the quinone in a Michael-type reaction, which is assisted by proton transfer from D174. The substrate-cocatalyst adduct is tautomerized with the assistance of Y404 as a proton donor. In the last stage, the paraquinone form of the tetrahydroxybenzene is reduced by Mo(IV)
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1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
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-
-
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REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
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reduction
-
-
-
-
transhydroxylation
-
-
-
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PATHWAY
KEGG Link
MetaCyc Link
Aminobenzoate degradation
-
gallate degradation III (anaerobic)
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
1,2,3,5-tetrahydroxybenzene:1,2,3-trihydroxybenzene hydroxytransferase
1,2,3,5-Tetrahydroxybenzene acts as a co-substrate for the conversion of pyrogallol into phloroglucinol, and for a number of similar isomerizations. The enzyme is provisionally listed here, but might be considered as the basis for a new class in the transferases, analogous to the aminotransferases.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
1,2,3,5-tetrahydroxybenzene-pyrogallol hydroxyltransferase
-
-
-
-
1,2,3,5-tetrahydroxybenzene:pyrogallol transhydroxylase
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-
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hydroxyltransferase, 1,2,3,5-tetrahydroxybenzene
-
-
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pyrogallol hydroxyltransferase
-
-
-
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pyrogallol phloroglucinol transhydroxylase
-
-
-
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pyrogallol:phloroglucinol hydroxyltransferase
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transhydroxylase
-
-
-
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CAS REGISTRY NUMBER
COMMENTARY
125978-84-9
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
alpha-subunit
SwissProt
Manually annotated by BRENDA team
beta-subunit
SwissProt
Manually annotated by BRENDA team
large and small subunit
-
-
Manually annotated by BRENDA team
Pelobacter acidigallici MaGal
strain MaGal 2
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
show the reaction diagram
-
-
-
?
1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
show the reaction diagram
Pelobacter acidigallici, Pelobacter acidigallici MaGal
-
-
tentatively identified
?
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene
1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
2,4,6,3’,4’,5’-hexahydroxydiphenyl ether and 3,4,5,3’,4’,5’-hexahydroxydiphenyl ether can substitute for the cocatalyst 1,2,3,5-tetrahydroxybenzene in vitro. This indicates that the diphenyl ethers can intrude into the active site and initiate the catalytic cycle
-
-
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
show the reaction diagram
-
-
-
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
show the reaction diagram
-
-
-
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
show the reaction diagram
-
-
tentatively identified
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
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pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
r
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
Pelobacter acidigallici MaGal
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
Pelobacter acidigallici MaGal
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
r
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
Pelobacter acidigallici MaGal
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
-
-
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
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-
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1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
Pelobacter acidigallici, Pelobacter acidigallici MaGal
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i.e. 1,2,3-trihydroxybenzene, reaction in fermentative degradation of trihydroxy-derivatives, pathway
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-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
Pelobacter acidigallici MaGal
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
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-
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1,2,3,5-tetrahydroxybenzene + resorcinol
phloroglucinol + hydroxyhydroquinone
show the reaction diagram
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-
-
?
1,2,3,5-tetrahydroxybenzene + resorcinol
phloroglucinol + hydroxyhydroquinone
show the reaction diagram
-
-
-
-
?
1,2,4,5-tetrahydroxybenzene + pyrogallol
hydroxyhydroquinone + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
-
-
-
?
hydroxyhydroquinone + hydroxyhydroquinone
resorcinol + 1,2,4,5-tetrahydroxybenzene
show the reaction diagram
-
-
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r
hydroxyhydroquinone + hydroxyhydroquinone
resorcinol + 1,2,4,5-tetrahydroxybenzene
show the reaction diagram
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-
tentatively identified
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hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
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hydroxyhydroquinone i.e. 1,2,4-trihydroxybenzene
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?
hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
show the reaction diagram
Pelobacter acidigallici, Pelobacter acidigallici MaGal
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hydroxyhydroquinone i.e. 1,2,4-trihydroxybenzene
resorcinol i.e. 1,3-benzenediol
?
additional information
?
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dimethyl sulfoxide at unphysiological high concentrations can replace 1,2,3,5-tetrahydroxybenzene with 0.04% efficiency, no transhydroxylation takes place with catechol or phenol + 1,2,3,5-tetrahydroxybenzene, pyrogallol + catechol, resorcinol, hydroquinone or phenol
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additional information
?
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dimethyl sulfoxide at unphysiological high concentrations can replace 1,2,3,5-tetrahydroxybenzene with 0.04% efficiency, no transhydroxylation takes place with catechol or phenol + 1,2,3,5-tetrahydroxybenzene, pyrogallol + catechol, resorcinol, hydroquinone or phenol
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additional information
?
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intermolecular transhydroxylation
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additional information
?
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1,2,4,5-tetrahydroxybenzene: OH-donor, pyrogallol, hydroxyhydroquinone and resorcinol: OH-acceptors
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additional information
?
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pyrogallol converts to phloroglucinol in the absence of added tetrahydroxybenzene if very little pyrogallol and high amounts of enzyme are present
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-
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additional information
?
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1,2,3,5-tetrahydroxybenzene, 1,2,4-trihydroxybenzene, effective OH-donors
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additional information
?
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1,2,3,5-tetrahydroxybenzene, 1,2,4-trihydroxybenzene, effective OH-donors, in the absence of OH-acceptor or at very high donor/acceptor ratio the donors react with themselves and disproportionate to hydroxylated and dehydroxylated products
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-
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additional information
?
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water is not the source of the added hydroxyl groups
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-
-
additional information
?
-
Pelobacter acidigallici MaGal
-
intermolecular transhydroxylation
-
-
-
additional information
?
-
Pelobacter acidigallici MaGal
-
dimethyl sulfoxide at unphysiological high concentrations can replace 1,2,3,5-tetrahydroxybenzene with 0.04% efficiency, no transhydroxylation takes place with catechol or phenol + 1,2,3,5-tetrahydroxybenzene, pyrogallol + catechol, resorcinol, hydroquinone or phenol, 1,2,3,5-tetrahydroxybenzene, 1,2,4-trihydroxybenzene, effective OH-donors
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-
-
additional information
?
-
Pelobacter acidigallici MaGal
-
water is not the source of the added hydroxyl groups
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-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
-
-
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
-
-
-
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
Pelobacter acidigallici, Pelobacter acidigallici MaGal
-
i.e. 1,2,3-trihydroxybenzene, reaction in fermentative degradation of trihydroxy-derivatives, pathway
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
show the reaction diagram
Pelobacter acidigallici MaGal
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
molybdenum cofactor
-
two molecules of molybdenum cofactor for each heterodimer, molybdenum is bound by a molybdopterin guanine dinucleotide
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Fe
-
iron-sulfur cluster
Fe
-
144 Fe atoms in 36 clusters per enzyme
Fe
P80563, P80564
three [4Fe-4S] centers in the beta subunit
Mo
-
enzyme contains Mo, 0.92 mol moybdenum per mol enzyme
Mo
-
12 molybdenum atoms per enzyme
Mo
P80563, P80564
active Mo-molybdopterin guanidine dinucleotide (MGD)2 site in the alpha-subunit
Molybdenum
-
molybdopterin-containing enzyme
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
resorcinol
-
complete inhibition of the reaction of hydroxyhydroquinone with itself
additional information
-
oxygen does not inactivate, but the assay requires strict anaerobiosis due to the instability of the substrates and products
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
-
no activation by reducing agents
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.71
-
1,2,3,5-Tetrahydroxybenzene
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.23
-
-
dimethyl sulfoxide
0.23
-
-
1,2,3,5-tetrahydroxybenzene + resorcinol
0.34
-
-
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
0.4
-
-
1,2,4,5-tetrahydroxybenzene
additional information
-
-
oxides tested as cosubstrates
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
130500
-
-
excluding cofactors, calculation from amino acid sequence
133000
-
-
mass spectrometry
160000
-
-
polar plot of self-rotation function
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
P80563, P80564
-
heterodimer
-
alpha,beta, 1 * 99260 + 1 * 31221, calculation from amino acid sequence
heterodimer
-
alpha,beta, 1 * 100400 + 1 * 31300, mass spectrometry
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
pyrogallol-phloroglucinol transhydroxylase complex and 1,2,4-trihydroxybenzene pyrogallol-phloroglucinol transhydroxylase complex. Crystal structure of the enzyme in the reduced Mo(IV) state, which is solved by single anomalous diffraction technique
P80563, P80564
OXIDATION STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
oxides replace the physiological cosubstrate, p.e. pyridine N-oxide, 2-hydroxypyridine N-oxide, DMSO and tetramethylene sulfoxide
-
437679
oxygen does not inactivate, but the assay requires strict anaerobiosis because of the instability of the substrates and products
-
437674
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli strain BL21 and M15
-