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1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
1,2,3,5-tetrahydroxybenzene + 1,2,3-trihydroxybenzene
1,3,5-trihydroxybenzene + 1,2,3,5-tetrahydroxybenzene
-
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
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
1,2,3,5-tetrahydroxybenzene + resorcinol
phloroglucinol + hydroxyhydroquinone
1,2,4,5-tetrahydroxybenzene + pyrogallol
hydroxyhydroquinone + 1,2,3,5-tetrahydroxybenzene
-
-
-
?
hydroxyhydroquinone + hydroxyhydroquinone
resorcinol + 1,2,4,5-tetrahydroxybenzene
hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
additional information
?
-
1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
-
-
tentatively identified
?
1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
-
-
tentatively identified
?
1,2,3,5-tetrahydroxybenzene + 1,2,3,5-tetrahydroxybenzene
phloroglucinol + pentahydroxybenzene
-
-
-
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
-
-
-
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
-
-
tentatively identified
?
1,2,3,5-tetrahydroxybenzene + hydroxyhydroquinone
phloroglucinol + 1,2,4,5-tetrahydroxybenzene
-
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
-
-
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
-
i.e. 1,2,3-trihydroxybenzene, reaction in fermentative degradation of trihydroxy-derivatives, pathway
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
-
i.e. 1,2,3-trihydroxybenzene, reaction in fermentative degradation of trihydroxy-derivatives, pathway
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
?
-
key step in the anaerobic degradation of gallic acid and releated polyphenolic compounds
-
-
?
1,2,3,5-tetrahydroxybenzene + pyrogallol
phloroglucinol + 1,2,3,5-tetrahydroxybenzene
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
pyrogallol i.e. 1,2,3-tri-hydroxybenzene
phloroglucinol i.e. 1,3,5-tri-hydroxybenzene
?
1,2,3,5-tetrahydroxybenzene + resorcinol
phloroglucinol + hydroxyhydroquinone
-
-
-
?
1,2,3,5-tetrahydroxybenzene + resorcinol
phloroglucinol + hydroxyhydroquinone
-
-
-
-
?
hydroxyhydroquinone + hydroxyhydroquinone
resorcinol + 1,2,4,5-tetrahydroxybenzene
-
-
tentatively identified
?
hydroxyhydroquinone + hydroxyhydroquinone
resorcinol + 1,2,4,5-tetrahydroxybenzene
-
-
-
r
hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
-
hydroxyhydroquinone i.e. 1,2,4-trihydroxybenzene
resorcinol i.e. 1,3-benzenediol
?
hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
-
hydroxyhydroquinone i.e. 1,2,4-trihydroxybenzene
resorcinol i.e. 1,3-benzenediol
?
hydroxyhydroquinone + pyrogallol
resorcinol + 1,2,3,5-tetrahydroxybenzene
-
hydroxyhydroquinone i.e. 1,2,4-trihydroxybenzene
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
intermolecular transhydroxylation
-
-
?
additional information
?
-
-
pyrogallol converts to phloroglucinol in the absence of added tetrahydroxybenzene if very little pyrogallol and high amounts of enzyme are present
-
-
?
additional information
?
-
-
1,2,3,5-tetrahydroxybenzene, 1,2,4-trihydroxybenzene, effective OH-donors
-
-
?
additional information
?
-
-
water is not the source of the added hydroxyl groups
-
-
?
additional information
?
-
-
water is not the source of the added hydroxyl groups
-
-
?
additional information
?
-
-
water is not the source of the added hydroxyl groups
-
-
?
additional information
?
-
-
water is not the source of the added hydroxyl groups
-
-
?
additional information
?
-
-
intermolecular transhydroxylation
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
1,2,3,5-tetrahydroxybenzene, 1,2,4-trihydroxybenzene, effective OH-donors
-
-
?
additional information
?
-
-
water is not the source of the added hydroxyl groups
-
-
?
additional information
?
-
-
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
-
-
?
additional information
?
-
-
1,2,4,5-tetrahydroxybenzene: OH-donor, pyrogallol, hydroxyhydroquinone and resorcinol: OH-acceptors
-
-
?
additional information
?
-
-
1,2,3,5-tetrahydroxybenzene, 1,2,4-trihydroxybenzene, effective OH-donors
-
-
?
additional information
?
-
-
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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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
-
brenda
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
brenda
Brune, A.; Schnell, S.; Schink, B.
Sequential transhydroxylations converting hydroxyhydroquinone to phloroglucinol in the strictly anaerobic, fermentative bacterium Pelobacter massiliensis
Appl. Environ. Microbiol.
58
1861-1868
1992
Pelobacter massiliensis
brenda
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
brenda
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
brenda
Reichenbecher, W.; Schink, B.
Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici
Biochim. Biophys. Acta
1430
245-253
1999
Pelobacter acidigallici
brenda
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
brenda
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
brenda
Paizs, C.; Bartlewski-Hof, U.; Retey, J.
Investigation of the mechanism of action of pyrogallol-phloroglucinol transhydroxylase by using putative intermediates
Chemistry
13
2805-2811
2007
Pelobacter acidigallici
brenda