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Literature summary for 1.3.1.57 extracted from

  • Conradt, D.; Hermann, B.; Gerhardt, S.; Einsle, O.; Müller, M.
    Biocatalytic properties and structural analysis of phloroglucinol reductases (2016), Angew. Chem. Int. Ed. Engl., 55, 15531-15534 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Eubacterium oxidoreducens
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Clostridium sp.
sequence comparisons, recombinant overexpression of His-tagged enzyme in Escherichia coli train BL21(DE3) Desulfosporosinus orientis

Crystallization (Commentary)

Crystallization (Comment) Organism
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 Clostridium sp.

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information Michaelis-Menten kinetics Desulfosporosinus orientis
additional information
-
additional information Michaelis-Menten kinetics Eubacterium oxidoreducens
additional information
-
additional information Michaelis-Menten kinetics Clostridium sp.

Molecular Weight [Da]

Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
78000
-
-
Eubacterium oxidoreducens
125000
-
-
Clostridium sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
phloroglucinol + NADPH + H+ Desulfosporosinus orientis
-
dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ Eubacterium oxidoreducens
-
dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ Clostridium sp.
-
dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ Eubacterium oxidoreducens AB3007
-
dihydrophloroglucinol + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Clostridium sp. U2C7W9
-
-
Desulfosporosinus orientis
-
-
-
Eubacterium oxidoreducens P57793
-
-
Eubacterium oxidoreducens AB3007 P57793
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography Desulfosporosinus orientis
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography Eubacterium oxidoreducens
recombinant His-tagged enzyme from Escherichia coli train BL21(DE3) by nickel affinity chromatography Clostridium sp.

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,4,6-trihydroxyacetophenone + NADPH + H+
-
Desulfosporosinus orientis 2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
-
Eubacterium oxidoreducens 2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
-
Clostridium sp. 2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
?
2,4,6-trihydroxyacetophenone + NADPH + H+
-
Eubacterium oxidoreducens AB3007 2-acetyl-3,5-dihydroxycyclohex-2-en-1-one + NADP+
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
-
Desulfosporosinus orientis 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
-
Eubacterium oxidoreducens 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
-
Clostridium sp. 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
?
2,4,6-trihydroxybenzaldehyde + NADPH + H+
-
Eubacterium oxidoreducens AB3007 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carbaldehyde + NADP+
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
-
Desulfosporosinus orientis methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
-
Eubacterium oxidoreducens methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
-
?
methyl 2,4,6-trihydroxybenzoate + NADPH + H+
-
Clostridium sp. methyl 2,4-dihydroxy-6-oxocyclohex-1-ene-1-carboxylate + NADP+
-
?
additional information 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 Clostridium sp. ?
-
?
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 Desulfosporosinus orientis ?
-
?
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 Eubacterium oxidoreducens ?
-
?
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 Eubacterium oxidoreducens AB3007 ?
-
?
phloroglucinol + NADPH + H+
-
Desulfosporosinus orientis dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+
-
Eubacterium oxidoreducens dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+
-
Clostridium sp. dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ conversion rate of 30%, 1HNMR analysis of the product Desulfosporosinus orientis dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ conversion rate of 36%, 1HNMR analysis of the product Eubacterium oxidoreducens dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ conversion rate of 37%, 1HNMR analysis of the product Clostridium sp. dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+
-
Eubacterium oxidoreducens AB3007 dihydrophloroglucinol + NADP+
-
?
phloroglucinol + NADPH + H+ conversion rate of 36%, 1HNMR analysis of the product Eubacterium oxidoreducens AB3007 dihydrophloroglucinol + NADP+
-
?

Subunits

Subunits Comment Organism
homodimer 2 * 39000, about Eubacterium oxidoreducens
homotetramer 4 * 30000, about Clostridium sp.

Synonyms

Synonyms Comment Organism
PGR
-
Desulfosporosinus orientis
PGR
-
Eubacterium oxidoreducens
PGR
-
Clostridium sp.
PGRcl
-
Clostridium sp.
PGRde
-
Desulfosporosinus orientis
PGReu
-
Eubacterium oxidoreducens

Cofactor

Cofactor Comment Organism Structure
NADPH Rossmann fold for cofactor binding Desulfosporosinus orientis
NADPH Rossmann fold for cofactor binding Eubacterium oxidoreducens
NADPH the NADPH binding motif is G24-X-X-G27-X-X-G30, Rossmann fold for cofactor binding Clostridium sp.

General Information

General Information Comment Organism
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 Desulfosporosinus orientis
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 Eubacterium oxidoreducens
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 Clostridium sp.
metabolism phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units Desulfosporosinus orientis
metabolism phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units Eubacterium oxidoreducens
metabolism phloroglucinol is a central intermediate in the degradation of flavonoids and tannins, overview. It is further degraded to acetate and butyrate units Clostridium sp.