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Literature summary extracted from

  • Whitman, C.; Aird, B.; Gillespie, W.; Stolowich, N.
    Chemical and enzymatic ketonization of 2-hydroxymuconate, a conjugated enol (1991), J. Am. Chem. Soc., 113, 3154-3162.
No PubMed abstract available

Cloned(Commentary)

EC Number Cloned (Comment) Organism
5.3.2.6 recombinant expression in Escherichia coli Pseudomonas putida

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
5.3.2.6 additional information
-
additional information kinetic modeling, overview Pseudomonas putida
5.3.2.6 0.145
-
2-hydroxymuconate pH 7.3, 30°C Pseudomonas putida
5.3.2.6 0.189
-
2-oxo-3-hexenedioate pH 7.3, 30°C Pseudomonas putida

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.3.2.6 2-hydroxymuconate Pseudomonas putida the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway 2-oxo-3-hexenedioate the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate r
5.3.2.6 2-hydroxymuconate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway 2-oxo-3-hexenedioate the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate r

Organism

EC Number Organism UniProt Comment Textmining
5.3.2.6 Pseudomonas putida
-
-
-
5.3.2.6 Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
5.3.2.6 recombinant enzyme from Escherichia coli by ultracentrifugation, two different steps of anion exchange chromatography, hydroxylapatite and hydrophobic interaction chromatography, and gel filtration with alternating steps of ultrafiltration Pseudomonas putida

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.3.2.6 2-hydroxy-4-trans-hexenedioate
-
Pseudomonas putida ?
-
?
5.3.2.6 2-hydroxy-4-trans-hexenedioate
-
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ?
-
?
5.3.2.6 2-hydroxymuconate ketonization Pseudomonas putida 2-oxo-3-hexenedioate
-
r
5.3.2.6 2-hydroxymuconate the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway Pseudomonas putida 2-oxo-3-hexenedioate the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate r
5.3.2.6 2-hydroxymuconate ketonization Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate
-
r
5.3.2.6 2-hydroxymuconate the conjugated enol, 2-hydroxymuconate is an unusually stable dienol that is reportedly generated in the course of bacterial catabolism of catechol by the enzymes of the meta-fission pathway Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate the dienol ketonizes chemically in aqueous solution and enzymatically by the action of 4-oxalocrotonate tautomerase to either the beta,gamma-unsaturated ketone or its alpha,beta-conjugated isomer 2-oxo-3-trans-hexenedioate r
5.3.2.6 2-oxo-3-hexenedioate
-
Pseudomonas putida 2-oxo-3-trans-hexenedioate
-
?
5.3.2.6 2-oxo-3-hexenedioate
-
Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-trans-hexenedioate
-
?
5.3.2.6 additional information substrate specificity, overview Pseudomonas putida ?
-
?
5.3.2.6 additional information substrate specificity, overview Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ?
-
?

Synonyms

EC Number Synonyms Comment Organism
5.3.2.6 4-OT
-
Pseudomonas putida
5.3.2.6 4-oxalocrotonate tautomerase
-
Pseudomonas putida

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
5.3.2.6 30
-
assay at Pseudomonas putida

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
5.3.2.6 139000
-
2-hydroxymuconate pH 7.3, 30°C Pseudomonas putida
5.3.2.6 288000
-
2-oxo-3-hexenedioate pH 7.3, 30°C Pseudomonas putida

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
5.3.2.6 7.3
-
assay at Pseudomonas putida

General Information

EC Number General Information Comment Organism
5.3.2.6 additional information immediate nonenzymatic conversion of 2-oxo-3-hexenedioate to 2-hydroxy-3-trans-hexenedioate with NaBH4. Rate constants for the nonenzymatic phosphate-catalyzed ketonization of 2-hydroxymuconate, overview Pseudomonas putida
5.3.2.6 physiological function 4-oxalocrotonate tautomerase is an extremely efficient catalyst apparently processing either isomer near the diffusion control limit of a small molecule and an enzyme Pseudomonas putida

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
5.3.2.6 957000
-
2-hydroxymuconate pH 7.3, 30°C Pseudomonas putida
5.3.2.6 1520000
-
2-oxo-3-hexenedioate pH 7.3, 30°C Pseudomonas putida