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Literature summary for 3.3.2.15 extracted from
- Structure and mechanism of Pseudomonas aeruginosa PhzD, an isochorismatase from the phenazine biosynthetic pathway (2003), Biochemistry, 42, 5684-5693.
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
- |
Pseudomonas aeruginosa |
Crystallization (Commentary)
| Crystallization (Comment) | Organism |
|---|---|
| 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
| Protein Variants | Comment | Organism |
|---|---|---|
| D38A | inactive variant | Pseudomonas aeruginosa |
| K122A | lower activity than mutant enzyme | Pseudomonas aeruginosa |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.004 | - |
isochorismate | pH 6.5 | Pseudomonas aeruginosa |  |
| 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 | |
| 0.983 | - |
chorismate | pH 6.5 | Pseudomonas aeruginosa | |
Molecular Weight [Da]
| Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|
| 23196 | - |
2 * 23196, calculated from sequence | Pseudomonas aeruginosa |
| 23478 | - |
2 * 23478, crystallization, light scattering | Pseudomonas aeruginosa |
| 49400 | - |
crystallization, light scattering | Pseudomonas aeruginosa |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (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
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Pseudomonas aeruginosa | Q7DC80 | - |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| wild-type and mutant enzymes | Pseudomonas aeruginosa |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| (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 |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (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 | ? | |
| (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 | ? | |
| chorismate + H2O | - |
Pseudomonas aeruginosa | ? | - |
? | |
| 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 | - |
? | |
| additional information | 4-amino-4-deoxychorismate is barely hydrolyzed | Pseudomonas aeruginosa | ? | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| dimer | 2 * 23196, calculated from sequence | Pseudomonas aeruginosa |
| dimer | 2 * 23478, crystallization, light scattering | Pseudomonas aeruginosa |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| PhzD | - |
Pseudomonas aeruginosa |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.2 | - |
isochorismate | pH 6.5 | Pseudomonas aeruginosa | |
| 1.2 | - |
chorismate | pH 6.5 | Pseudomonas aeruginosa | |
| 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
| General Information | Comment | Organism |
|---|---|---|
| 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]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 1.2 | - |
chorismate | pH 6.5 | Pseudomonas aeruginosa | |
| 50 | - |
isochorismate | pH 6.5 | Pseudomonas aeruginosa | |
| 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 | |
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