Reaction participants Show >> << Hide
- Name help_outline 2-amino-4,5-dihydroxy-6-oxo-7-(phosphooxy)heptanoate Identifier CHEBI:58898 Charge -2 Formula C7H12NO9P InChIKeyhelp_outline OABFYXXSGQYCAM-UHFFFAOYSA-L SMILEShelp_outline [NH3+]C(CC(O)C(O)C(=O)COP([O-])([O-])=O)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-aspartate 4-semialdehyde Identifier CHEBI:537519 Charge 0 Formula C4H7NO3 InChIKeyhelp_outline HOSWPDPVFBCLSY-VKHMYHEASA-N SMILEShelp_outline [H]C(=O)C[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 14 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline dihydroxyacetone phosphate Identifier CHEBI:57642 (Beilstein: 4428349) help_outline Charge -2 Formula C3H5O6P InChIKeyhelp_outline GNGACRATGGDKBX-UHFFFAOYSA-L SMILEShelp_outline C(CO)(COP([O-])(=O)[O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 41 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:26313 | RHEA:26314 | RHEA:26315 | RHEA:26316 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Novel benzene ring biosynthesis from C(3) and C(4) primary metabolites by two enzymes.
Suzuki H., Ohnishi Y., Furusho Y., Sakuda S., Horinouchi S.
The shikimate pathway, including seven enzymatic steps for production of chorismate via shikimate from phosphoenolpyruvate and erythrose-4-phosphate, is common in various organisms for the biosynthesis of not only aromatic amino acids but also most biogenic benzene derivatives. 3-Amino-4-hydroxybe ... >> More
The shikimate pathway, including seven enzymatic steps for production of chorismate via shikimate from phosphoenolpyruvate and erythrose-4-phosphate, is common in various organisms for the biosynthesis of not only aromatic amino acids but also most biogenic benzene derivatives. 3-Amino-4-hydroxybenzoic acid (3,4-AHBA) is a benzene derivative serving as a precursor for several secondary metabolites produced by Streptomyces, including grixazone produced by Streptomyces griseus. Our study on the biosynthesis pathway of grixazone led to identification of the biosynthesis pathway of 3,4-AHBA from two primary metabolites. Two genes, griI and griH, within the grixazone biosynthesis gene cluster were found to be responsible for the biosynthesis of 3,4-AHBA; the two genes conferred the in vivo production of 3,4-AHBA even on Escherichia coli. In vitro analysis showed that GriI catalyzed aldol condensation between two primary metabolites, l-aspartate-4-semialdehyde and dihydroxyacetone phosphate, to form a 7-carbon product, 2-amino-4,5-dihydroxy-6-one-heptanoic acid-7-phosphate, which was subsequently converted to 3,4-AHBA by GriH. The latter reaction required Mn(2+) ion but not any cofactors involved in reduction or oxidation. This pathway is independent of the shikimate pathway, representing a novel, simple enzyme system responsible for the synthesis of a benzene ring from the C(3) and C(4) primary metabolites. << Less
J. Biol. Chem. 281:36944-36951(2006) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.