EC Number   |
Substrates |
Organism |
Products |
Reversibility |
|---|
  5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid |
- |
Pseudomonas fluorescens |
(1R,6S)-6-amino-5-hydroxycyclohexa-2,4-diene-1-carboxylic acid |
- |
? |
| 5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxyate |
i.e. trans-2,3-dihydro-3-hydroxyanthranilic acid |
Pseudomonas fluorescens |
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylate |
i.e. 2,3-dihydro-3-hydroxy-anthranilate |
? |
| 5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxyate |
i.e. trans-2,3-dihydro-3-hydroxyanthranilic acid. The enzyme is involved in phenazine synthesis |
Pseudomonas fluorescens |
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylate |
i.e. 2,3-dihydro-3-hydroxy-anthranilate |
? |
| 5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxyate |
charactierzation of the product by NMR spectrometry. The structure of PhzF in complex with its substrate, trans-2,3-dihydro-3-hydroxyanthranilic acid, suggests that it is an isomerase using the conserved glutamate45 to abstract a proton from C3 of the substrate. The proposed mechanism involves proton abstraction from C3 of trans-2,3-dihydro-3-hydroxyanthranilate by Glu45, followed by rearrangement of the double bonds and reprotonation at C1. The function of E45 as a proton shuttle is supported by results from NMR spectroscopy |
Pseudomonas fluorescens |
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylate |
- |
? |
| 5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxyate |
PhzF is capable of producing phenazine-1-carboxylic acid, albeit slowly, from trans-2,3-dihydro-3-hydroxyanthranilic acid (i.e. (5S,6R)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxylic acid). These observations suggest that PhzF catalyzes the initial step in the conversion of trans-2,3-dihydro-3-hydroxyanthranilic acid to phenazine-1-carboxylic acid, probably via a rearrangement reaction yielding the more reactive 3-oxo analogue of trans-2,3-dihydro-3-hydroxyanthranilic acid, and that subsequent steps can occur spontaneously. A hypothetical model for how trans-2,3-dihydro-3-hydroxyanthranilic acid binds to the PhzF active site suggests that Glu45 and Asp208 could act as general acid-base catalysts in a rearrangement reaction |
Pseudomonas fluorescens |
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylate |
i.e. 2,3-dihydro-3-hydroxy-anthranilate |
? |
| 5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxyate |
i.e. trans-2,3-dihydro-3-hydroxyanthranilic acid |
Pseudomonas fluorescens Feb 79 |
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylate |
i.e. 2,3-dihydro-3-hydroxy-anthranilate |
? |
| 5.3.3.17 | (5S,6S)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxyate |
PhzF is capable of producing phenazine-1-carboxylic acid, albeit slowly, from trans-2,3-dihydro-3-hydroxyanthranilic acid (i.e. (5S,6R)-6-amino-5-hydroxycyclohexane-1,3-diene-1-carboxylic acid). These observations suggest that PhzF catalyzes the initial step in the conversion of trans-2,3-dihydro-3-hydroxyanthranilic acid to phenazine-1-carboxylic acid, probably via a rearrangement reaction yielding the more reactive 3-oxo analogue of trans-2,3-dihydro-3-hydroxyanthranilic acid, and that subsequent steps can occur spontaneously. A hypothetical model for how trans-2,3-dihydro-3-hydroxyanthranilic acid binds to the PhzF active site suggests that Glu45 and Asp208 could act as general acid-base catalysts in a rearrangement reaction |
Pseudomonas fluorescens Feb 79 |
(1R,6S)-6-amino-5-oxocyclohex-2-ene-1-carboxylate |
i.e. 2,3-dihydro-3-hydroxy-anthranilate |
? |
