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Information on EC 1.3.1.57 - phloroglucinol reductase
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1.3.1.57 phloroglucinol reductaseIUBMB Comments
Involved in the gallate anaerobic degradation pathway in bacteria.
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Word Map
- 1.3.1.57
- eubacterium
- copper
- rumen
-
dearomatization
- butyrate
- phenol
- p-chloromercuribenzoate
- air
The enzyme appears in viruses and cellular organisms
Synonyms
phloroglucinol reductase, pgrcl, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
PGR
PGReu
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dihydrophloroglucinol + NADP+ = phloroglucinol + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
dihydrophloroglucinol:NADP+ oxidoreductase
Involved in the gallate anaerobic degradation pathway in bacteria.
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CAS REGISTRY NUMBER
COMMENTARY
80804-59-7
-
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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
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
U2C7W9
-
-
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
-
-
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
-
-
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
-
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
Eubacterium oxidoreducens AB3007
-
-
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
-
-
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
U2C7W9
-
-
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
-
-
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
-
-
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
-
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
Eubacterium oxidoreducens AB3007
-
-
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
-
-
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
U2C7W9
-
-
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
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-
-
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
-
-
-
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
-
-
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
-
-
-
-
?
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
reverse reaction about 36fold slower then that of the forward reaction
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
reverse reaction about 36fold slower then that of the forward reaction
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
pathway of anaerobic degradation of trihydroxybenzenes and metabolism of gallic acid
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
-
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
pathway of anaerobic degradation of trihydroxybenzenes and metabolism of gallic acid
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP+
-
-
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP+
-
-
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP+
-
-
-
r
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
U2C7W9
conversion rate of 37%, 1HNMR analysis of the product
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
-
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
-
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
conversion rate of 30%, 1HNMR analysis of the product
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
conversion rate of 36%, 1HNMR analysis of the product
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
Eubacterium oxidoreducens AB3007
conversion rate of 36%, 1HNMR analysis of the product
-
-
?
additional information
?
-
U2C7W9
analysis of substrate speccificity, enzymatic dearomatization of monoaromatic phenol derivatives, narrow substrate range, overview. No activity with 26 different compounds, including bicyclic compounds such as flaviolin and 2-tetralone, and several aromatic and nonaromatic monocyclic compounds
-
-
?
additional information
?
-
-
analysis of substrate specificity, enzymatic dearomatization of monoaromatic phenol derivatives, narrow substrate range, overview. No activity with 26 different compounds, including bicyclic compounds such as flaviolin and 2-tetralone, and several aromatic and nonaromatic monocyclic compounds
-
-
?
additional information
?
-
analysis of substrate specificity, enzymatic dearomatization of monoaromatic phenol derivatives, narrow substrate range, overview. No activity with methyl 2,4,6-trihydroxybenzoate and with 26 different compounds, including bicyclic compounds such as flaviolin and 2-tetralone, and several aromatic and nonaromatic monocyclic compounds
-
-
?
additional information
?
-
Eubacterium oxidoreducens AB3007
analysis of substrate specificity, enzymatic dearomatization of monoaromatic phenol derivatives, narrow substrate range, overview. No activity with methyl 2,4,6-trihydroxybenzoate and with 26 different compounds, including bicyclic compounds such as flaviolin and 2-tetralone, and several aromatic and nonaromatic monocyclic compounds
-
-
?
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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
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
reverse reaction about 36fold slower then that of the forward reaction
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
reverse reaction about 36fold slower then that of the forward reaction
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
pathway of anaerobic degradation of trihydroxybenzenes and metabolism of gallic acid
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
-
-
r
phloroglucinol + NADPH
dihydrophloroglucinol + NADP
-
pathway of anaerobic degradation of trihydroxybenzenes and metabolism of gallic acid
-
r
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
-
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
-
-
-
?
phloroglucinol + NADPH + H+
dihydrophloroglucinol + NADP+
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
U2C7W9
the NADPH binding motif is G24-X-X-G27-X-X-G30, Rossmann fold for cofactor binding
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,4,6-Trihydroxybenzoate
-
tested at 1.0 mM and under N2, 49% inhibition
8-hydroxyquinoline
-
enzyme preincubated with the inhibitor, 0.00166 mM, for 60 min at room temperature before the addition of the substrate, 83% inhibition
EDTA
-
enzyme preincubated with the inhibitor, 0.00333 mM, for 60 min at room temperature before the addition of the substrate, 11% inhibition
hydroxylamine
-
enzyme preincubated with the inhibitor, 0.00166 mM, for 60 min at room temperature before the addition of the substrate, 9% inhibition
iodacetate
-
enzyme preincubated with the inhibitor, 0.00166 mM, for 60 min at room temperature before the addition of the substrate, 21% inhibition
o-phenanthroline
-
enzyme preincubated with the inhibitor, 0.00166 mM, for 60 min at room temperature before the addition of the substrate, 71% inhibition
p-chloromercuribenzoate
-
enzyme preincubated with the inhibitor, 0.00166 mM, for 60 min at room temperature before the addition of the substrate, 48% inhibition
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
Michaelis-Menten kinetics
-
additional information
additional information
Michaelis-Menten kinetics
-
additional information
additional information
U2C7W9
Michaelis-Menten kinetics
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
evolution
-
phloroglucinol reductases, PGRs, are members of the family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDRs), PGR subfamily. Several amino acid positions are identified as being conserved within the PGR subfamily and might be involved in substrate differentiation
evolution
phloroglucinol reductases, PGRs, are members of the family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDRs), PGR subfamily. Several amino acid positions were identified as being conserved within the PGR subfamily and might be involved in substrate differentiation
evolution
U2C7W9
phloroglucinol reductases, PGRs, are members of the family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDRs), PGR subfamily. Several amino acid positions were identified as being conserved within the PGR subfamily and might be involved in substrate differentiation
evolution
Eubacterium oxidoreducens AB3007
-
phloroglucinol reductases, PGRs, are members of the family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDRs), PGR subfamily. Several amino acid positions were identified as being conserved within the PGR subfamily and might be involved in substrate differentiation
-
metabolism
-
phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units
metabolism
phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units
metabolism
U2C7W9
phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units
metabolism
Eubacterium oxidoreducens AB3007
-
phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units
-
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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). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
78000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
homodimer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
three dimensional structures of PGRcl in the apo form and with bound NADPH are determined to 1.7 A and 1.8 A resolution, respectively. The enzyme crystallizes as a homotetramer (125 kDa), with two monomers in the asymmetric unit
U2C7W9
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4
-
crude enzyme shows a loss activity over a 5-day period, in presence of 1 mM of either 2-mercaptoethanol, dithiothreitol, or glutathione, or combinations of these reagents, is protected from the loss of enzyme activity
additional information
-
a rapid decay of the enzyme activity in water bath at 53°C, less then 10% of the initial activity remains after 2.5 min
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
stable for several hours when kept on ice and retained full activity being frozen with 15% glycerol in liquid N2. Incubation at 30°C and pH 7.0, 82% of initial activity retained after 3.3 h
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
prepared of a cell extract by French press, DEAE-cellulose column, phenyl-Sepharose column, ultrafiltration, red agarose column, anion exchange column, purified 90.4fold with a yield of 29%
-
protamine sulfate precipitation, ammonium sulfate precipitation, centrifugation steps, dialysis, gel filtration
-
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography
-
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography
U2C7W9
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli train BL21(DE3)
-
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
U2C7W9
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Krumholz, L.R.; Crawford, R.L.; Hemling, M.E.; Bryant, M.P.
Metabolism of gallate and phloroglucinol in Eubacterium oxidoreducens via 3-hydroxy-5-oxohexanoate
J. Bacteriol.
169
1886-1890
1987
Eubacterium oxidoreducens, Eubacterium oxidoreducens G-41
brenda
Haddock, J.D.; Ferry, J.G.
Purification and properties of phloroglucinol reductase from Eubacterium oxidoreducens G-41
J. Biol. Chem.
264
4423 - 4427
1989
Eubacterium oxidoreducens, Eubacterium oxidoreducens G-41
brenda
Patel, T.R.; Jure, K.G.; Jones, G.A.
Catabolism of phloroglucinol by the rumen anaerobe Coprococcus
Appl. Environ. Microbiol.
42
1010 - 1017
1981
Coprococcus sp., Coprococcus sp. Pe5
brenda
Conradt, D.; Hermann, B.; Gerhardt, S.; Einsle, O.; Mller, M.
Biocatalytic properties and structural analysis of phloroglucinol reductases
Angew. Chem. Int. Ed. Engl.
55
15531-15534
2016
Desulfosporosinus orientis, Eubacterium oxidoreducens (P57793), Clostridium sp. (U2C7W9), Eubacterium oxidoreducens AB3007 (P57793)
brenda
Husain, S.; Mueller, M.
Fungal dihydroxynaphthalene-melanin diversity-oriented biosynthesis through enzymatic and non-enzymatic transformations
Synlett
28
2360-2372
2017
Desulfosporosinus orientis, Clostridium sp. ATCC BAA-442, Eubacterium sp. AB3007
-
brenda
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