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Information on EC 1.97.1.2 - pyrogallol hydroxytransferase and Organism(s) Pelobacter acidigallici and UniProt Accession P80563
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1.97.1.2 pyrogallol hydroxytransferaseIUBMB Comments
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.
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Word Map
- 1.97.1.2
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pelobacter
- molybdenum
- heterodimer
- epr
- beta-subunits
- p-chloromercuribenzoate
- sulfide
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cosubstrate
- dithionite
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acid-labile
- acetylene
- desulfovibrio
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trihydroxybenzenes
- tungsten
- molybdopterin
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dehydroxylation
- 1,2,4-trihydroxybenzene
- phenol
- dimethylsulfoxide
- hydroxyhydroquinone
- guanine
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hydratase
- alpha-subunit
The taxonomic range for the selected organisms is: Pelobacter acidigallici
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
Synonyms
transhydroxylase, pyrogallol:phloroglucinol hydroxyltransferase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
1,2,3,5-tetrahydroxybenzene-pyrogallol hydroxyltransferase
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1,2,3,5-tetrahydroxybenzene:pyrogallol transhydroxylase
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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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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
a mechanism is proposed which combines an oxidative hydroxylation with a reductive dehydroxylation via molybdenum cofactor
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1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene = 1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
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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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
redox reaction
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oxidation
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reduction
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transhydroxylation
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PATHWAY SOURCE
PATHWAYS
BRENDA
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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.
CAS REGISTRY NUMBER
COMMENTARY
125978-84-9
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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
1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
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tentatively identified
?
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene
1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
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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
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?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
1,2,3,5-tetrahydroxybenzene + resorcinol
phloroglucinol + hydroxyhydroquinone
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?
hydroxyhydroquinone + hydroxyhydroquinone
resorcinol + 1,2,4,5-tetrahydroxybenzene
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tentatively identified
?
hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
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hydroxyhydroquinone i.e. 1,2,4-trihydroxybenzene
resorcinol i.e. 1,3-benzenediol
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
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?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
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tentatively identified
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1,2,3,5-tetrahydroxybenzene + pyrogallol
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key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
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?
1,2,3,5-tetrahydroxybenzene + pyrogallol
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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
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
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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
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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
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pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
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1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
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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
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pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
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1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
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pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
r
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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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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?
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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water is not the source of the added hydroxyl groups
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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
?
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water is not the source of the added hydroxyl groups
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?
additional information
?
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water is not the source of the added hydroxyl groups
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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
1,2,3,5-tetrahydroxybenzene + pyrogallol
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key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
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?
1,2,3,5-tetrahydroxybenzene + pyrogallol
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i.e. 1,2,3-trihydroxybenzene, reaction in fermentative degradation of trihydroxy-derivatives, pathway
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
molybdenum cofactor
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two molecules of molybdenum cofactor for each heterodimer, molybdenum is bound by a molybdopterin guanine dinucleotide
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mo
active Mo-molybdopterin guanidine dinucleotide (MGD)2 site in the alpha-subunit
Fe
Mo
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
resorcinol
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complete inhibition of the reaction of hydroxyhydroquinone with itself
additional information
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oxygen does not inactivate, but the assay requires strict anaerobiosis due to the instability of the substrates and products
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
31221
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alpha,beta, 1 * 99260 + 1 * 31221, calculation from amino acid sequence
99260
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alpha,beta, 1 * 99260 + 1 * 31221, calculation from amino acid sequence
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
heterodimer
heterodimer
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alpha,beta, 1 * 99260 + 1 * 31221, calculation from amino acid sequence
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
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
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
oxides replace the physiological cosubstrate, p.e. pyridine N-oxide, 2-hydroxypyridine N-oxide, DMSO and tetramethylene sulfoxide
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437679
oxygen does not inactivate, but the assay requires strict anaerobiosis because of the instability of the substrates and products
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437674
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Brune, A.; Schink, B.
Phloroglucinol pathway in the strictly anaerobic Pelobacter acidigallici: fermentation of trihydroxybenzenes to acetate via triacetic acid
Arch. Microbiol.
157
417-424
1992
Pelobacter acidigallici, Pelobacter acidigallici MaGal 2
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Brune, A.; Schink, B.
Pyrogallol-to-phloroglucinol conversion and other hydroxyl-transfer reactions catalyzed by cell extracts of Pelobacter acidigallici
J. Bacteriol.
172
1070-1076
1990
Pelobacter acidigallici, Pelobacter acidigallici MaGal 2
Baas, D.; Retey, J.
Cloning, sequencing and heterologous expression of pyrogallol-phloroglucinol transhydroxylase from Pelobacter acidigallici
Eur. J. Biochem.
265
896-901
1999
Pelobacter acidigallici
Reichenbecher, W.; Ruediger, A.; Kroneck, P.M.H.; Schink, B.
One molecule of molybdopterin guanine dinucleotide is associated with each subunit of the heterodimeric Mo-Fe-S protein transhydroxylase of Pelobacter acidigallici as determined by SDS/PAGE and mass spectrometry
Eur. J. Biochem.
237
406-413
1996
Pelobacter acidigallici
Reichenbecher, W.; Schink, B.
Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici
Biochim. Biophys. Acta
1430
245-253
1999
Pelobacter acidigallici
Abt, D.J.; Einsle, O.; Niessen, H.; Krieger, R.; Messerschmidt, A.; Schink, B.; Kroneck, P.M.H.
Crystallization and preliminary x-ray analysis of the molybdenum-dependent pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici
Acta Crystallogr. Sect. D
58
343-345
2002
Pelobacter acidigallici, Pelobacter acidigallici MaGal 2
Messerschmidt, A.; Niessen, H.; Abt, D.; Einsle, O.; Schink, B.; Kroneck, P.M.
Crystal structure of pyrogallol-phloroglucinol transhydroxylase, an Mo enzyme capable of intermolecular hydroxyl transfer between phenols
Proc. Natl. Acad. Sci. USA
101
11571-11576
2004
Pelobacter acidigallici (P80563), Pelobacter acidigallici (P80564), Pelobacter acidigallici
EXTERNAL LINKS (specific for EC-Number 1.97.1.2)
Transporter Classification Database (TCDB): 5.A.3.7.1
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