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Literature summary extracted from

  • Parsons, J.F.; Calabrese, K.; Eisenstein, E.; Ladner, J.E.
    Structure and mechanism of Pseudomonas aeruginosa PhzD, an isochorismatase from the phenazine biosynthetic pathway (2003), Biochemistry, 42, 5684-5693.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.3.2.15
-
 Pseudomonas aeruginosa

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
3.3.2.15 hanging drops by vapor diffusion method, 1.5 A crystal structure of native PhzD, and the 1.6 A structure of the inactive D38A variant in complex with isochorismate Pseudomonas aeruginosa

Protein Variants

EC Number Protein Variants Comment Organism
3.3.2.15 D38A inactive variant Pseudomonas aeruginosa
3.3.2.15 K122A lower activity than mutant enzyme Pseudomonas aeruginosa

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
3.3.2.15 0.004
-
 isochorismate pH 6.5 Pseudomonas aeruginosa
3.3.2.15 0.068
-
 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate i.e. 2-amino-2-deoxy-isochorismate, pH 6.5 Pseudomonas aeruginosa
3.3.2.15 0.983
-
 chorismate pH 6.5 Pseudomonas aeruginosa

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
3.3.2.15 23196
-
 2 * 23196, calculated from sequence Pseudomonas aeruginosa
3.3.2.15 23478
-
 2 * 23478, crystallization, light scattering Pseudomonas aeruginosa
3.3.2.15 49400
-
 crystallization, light scattering Pseudomonas aeruginosa

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.3.2.15 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate + H2O Pseudomonas aeruginosa i.e. 2-amino-2-deoxy-isochorismate. The enzyme is involved in phenazine biosynthesis (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid + pyruvate i.e. trans-2,3-dihydro-3-hydroxyanthranilate ?

Organism

EC Number Organism UniProt Comment Textmining
3.3.2.15 Pseudomonas aeruginosa Q7DC80
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.3.2.15 wild-type and mutant enzymes Pseudomonas aeruginosa

Reaction

EC Number Reaction Comment Organism Reaction ID
3.3.2.15 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate + H2O = (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid + pyruvate mechanism in which the carboxylate acts as a general acid to protonate the substrate, yielding a carbocation/oxocarbonium ion that is then rapidly hydrated to form a hemiketal intermediate, which then decomposes spontaneously to products Pseudomonas aeruginosa
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.3.2.15 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate + H2O i.e. 2-amino-2-deoxy-isochorismate. The enzyme is involved in phenazine biosynthesis Pseudomonas aeruginosa (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid + pyruvate i.e. trans-2,3-dihydro-3-hydroxyanthranilate ?
3.3.2.15 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate + H2O i.e. 2-amino-2-deoxy-isochorismate. Slightly more efficiently hydrolyzed than isochorismate. Hydrolysis of the vinyl ether functional group. Slightly more efficiently than it hydrolyzes isochorismate Pseudomonas aeruginosa (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid + pyruvate i.e. trans-2,3-dihydro-3-hydroxyanthranilate ?
3.3.2.15 chorismate + H2O
-
 Pseudomonas aeruginosa ?
-
 ?
3.3.2.15 isochorismate + H2O hydrolyzed slightly less efficiently than (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate (i.e. 2-amino-2-deoxy-isochorismate) Pseudomonas aeruginosa 2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate
-
 ?
3.3.2.15 additional information 4-amino-4-deoxychorismate is barely hydrolyzed Pseudomonas aeruginosa ?
-
 ?

Subunits

EC Number Subunits Comment Organism
3.3.2.15 dimer 2 * 23196, calculated from sequence Pseudomonas aeruginosa
3.3.2.15 dimer 2 * 23478, crystallization, light scattering Pseudomonas aeruginosa

Synonyms

EC Number Synonyms Comment Organism
3.3.2.15 PhzD
-
 Pseudomonas aeruginosa

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3.3.2.15 0.2
-
 isochorismate pH 6.5 Pseudomonas aeruginosa
3.3.2.15 1.2
-
 chorismate pH 6.5 Pseudomonas aeruginosa
3.3.2.15 7.3
-
 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate i.e. 2-amino-2-deoxy-isochorismate, pH 6.5 Pseudomonas aeruginosa

General Information

EC Number General Information Comment Organism
3.3.2.15 physiological function the enzyme is involved in phenazine biosynthesis. Phenazines are antimicrobial compounds that provide Pseudomonas with a competitive advantage in certain environments and may be partly responsible for the persistence of Pseudomonas infections Pseudomonas aeruginosa

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
3.3.2.15 1.2
-
 chorismate pH 6.5 Pseudomonas aeruginosa
3.3.2.15 50
-
 isochorismate pH 6.5 Pseudomonas aeruginosa
3.3.2.15 107
-
 (5S,6S)-6-amino-5-[(1-carboxyethenyl)oxy]cyclohexa-1,3-diene-1-carboxylate i.e. 2-amino-2-deoxy-isochorismate, pH 6.5 Pseudomonas aeruginosa