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Literature summary extracted from

  • Wang, S.; Johnson Jr., W.; Czerwinski, R.; Stamps, S.; Whitman, C.
    Kinetic and stereochemical analysis of YwhB, a 4-oxalocrotonate tautomerase homologue in Bacillus subtilis: Mechanistic implications for the YwhB- and 4-oxalocrotonate tautomerase-catalyzed reactions (2007), Biochemistry, 46, 11919-11929.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
5.3.2.6 expression of wild-type and mutant YwhBs in Escherichia coli strain BL21(DE3)pLysS Bacillus subtilis

Protein Variants

EC Number Protein Variants Comment Organism
5.3.2.6 P1A site-directed mutagenesis, inactive mutant Bacillus subtilis
5.3.2.6 R11A site-directed mutagenesis, inactive mutant Bacillus subtilis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.3.2.6 2-hydroxy-2,4-pentadienoate Bacillus subtilis
-
 2-oxopent-3-enoic acid
-
 ?
5.3.2.6 2-oxo-4-hexenedioate Pseudomonas putida via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate 2-oxo-3-hexenedioate
-
 ?
5.3.2.6 2-oxo-4-hexenedioate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate 2-oxo-3-hexenedioate
-
 ?
5.3.2.6 phenylenolpyruvate Bacillus subtilis
-
 phenylpyruvate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
5.3.2.6 Bacillus subtilis
-
-
-
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 wild-type and mutant YwhBs from Escherichia coli strain BL21(DE3)pLysS Bacillus subtilis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.3.2.6 (2Z,4E)-2-hydroxyhexa-2,4-dienedioate 1,3- and 1,5-keto-enol tautomerization reactions are observed for 2-hydroxy-2,4-hexadienedioate. YwhB converts it to the 3S isomer of 2-oxo-4-hexenedioate in a highly stereoselective manner Bacillus subtilis (2E)-5-oxohex-2-enedioate main product ?
5.3.2.6 2-hydroxy-2,4-hexadienedioate 4-OT with 2-hydroxy-2,4-hexadienedioate in D2O results in a racemic mixture of 2-oxo-[3-2H]-4-hexenedioate, suggesting that 4-OT may not catalyze a 1,3-keto-enol tautomerization reaction using this dienol Pseudomonas putida 2-oxo-3,4-hexenedioate
-
 ?
5.3.2.6 2-hydroxy-2,4-hexadienedioate 4-OT with 2-hydroxy-2,4-hexadienedioate in D2O results in a racemic mixture of 2-oxo-[3-2H]-4-hexenedioate, suggesting that 4-OT may not catalyze a 1,3-keto-enol tautomerization reaction using this dienol Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3,4-hexenedioate
-
 ?
5.3.2.6 2-hydroxy-2,4-pentadienoate
-
 Bacillus subtilis 2-oxopent-3-enoic acid
-
 ?
5.3.2.6 2-oxo-4-hexenedioate via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate Pseudomonas putida 2-oxo-3-hexenedioate
-
 ?
5.3.2.6 2-oxo-4-hexenedioate via the intermediate 2-hydroxy-2,4-hexadienedioate, i.e. 2-hydroxymuconate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 2-oxo-3-hexenedioate
-
 ?
5.3.2.6 additional information ketonization of two monoacid substrates, 2-hydroxy-2,4-pentadienoate and phenylenolpyruvate, produces a mixture of stereoisomers, 2-keto-3-[2H]-4-pentenoate and 3-[2H]-phenylpyruvate, where the (3R)-isomers predominate Pseudomonas putida ?
-
 ?
5.3.2.6 additional information YwhB has a relatively non-specific 1,3- and 1,5-keto-enol tautomerase activity, converting 2-hydroxy-2,4-pentadienoate to 2-oxo-4-pentenoate, and phenylenolpyruvate to phenylpyruvate. But YwhB is a more efficient 1,3-keto-enol tautomerase than it is a 1,5-keto-enol tautomerase, and residues Pro-1 and Arg-11 are critical residues for these two activities Bacillus subtilis ?
-
 ?
5.3.2.6 additional information ketonization of two monoacid substrates, 2-hydroxy-2,4-pentadienoate and phenylenolpyruvate, produces a mixture of stereoisomers, 2-keto-3-[2H]-4-pentenoate and 3-[2H]-phenylpyruvate, where the (3R)-isomers predominate Pseudomonas putida mt-2 / ATCC 33015 / DSM 3931 / NCIB 12182 / NCIMB 12182 ?
-
 ?
5.3.2.6 phenylenolpyruvate
-
 Bacillus subtilis phenylpyruvate
-
 ?

Subunits

EC Number Subunits Comment Organism
5.3.2.6 hexamer
-
 Bacillus subtilis
5.3.2.6 hexamer
-
 Pseudomonas putida

Synonyms

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

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
5.3.2.6 23
-
 assay at Bacillus subtilis
5.3.2.6 23
-
 assay at Pseudomonas putida

pH Optimum

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

General Information

EC Number General Information Comment Organism
5.3.2.6 malfunction covalent modification of Pro-1 by 3-bromopropiolate inactivates YwhB, implicating Pro-1 as a critical catalytic residue in the conversion of phenylenolpyruvate to phenylpyruvate Bacillus subtilis