prephenic acid
2,5-cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-alpha-oxo-
Identification
| Name | prephenic acid |
| IUPAC | 1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid |
| CAS Number | 126-49-8 |
| FDA UNII | Z66B98Z97I |
| Molecular Formula | C10 H10 O6 |
| Molecular Weight | 226.18490000 |
| Nikkaji Number | J38.009A |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for prephenic acid usage levels up to | not for fragrance use. |
| Recommendation for prephenic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
1-(2-
carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
1-
carboxy-4-hydroxy-2,5-cyclohexadiene-1-pyruvic acid
2,5-
cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-alpha-oxo-
PubMed:
Steered Molecular Dynamics Methods Applied to Enzyme Mechanism and Energetics.
PubMed:
Screening of Satureja subspicata Vis. Honey by HPLC-DAD, GC-FID/MS and UV/VIS: Prephenate Derivatives as Biomarkers.
PubMed:
Electrostatic transition state stabilization rather than reactant destabilization provides the chemical basis for efficient chorismate mutase catalysis.
PubMed:
In vivo instability of chorismate causes substrate loss during fermentative production of aromatics.
PubMed:
Structure-guided discovery of the metabolite carboxy-SAM that modulates tRNA function.
PubMed:
Mapping enzymatic catalysis using the effective fragment molecular orbital method: towards all ab initio biochemistry.
PubMed:
Identification of a metagenome-derived prephenate dehydrogenase gene from an alkaline-polluted soil microorganism.
PubMed:
Interaction between DAHP synthase and chorismate mutase endows new regulation on DAHP synthase activity in Corynebacterium glutamicum.
PubMed:
Characterisation of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark.
PubMed:
Molecular dynamics simulation of the last step of a catalytic cycle: product release from the active site of the enzyme chorismate mutase from Mycobacterium tuberculosis.
PubMed:
Stereochemical outcome at four stereogenic centers during conversion of prephenate to tetrahydrotyrosine by BacABGF in the bacilysin pathway.
PubMed:
Olefin isomerization regiochemistries during tandem action of BacA and BacB on prephenate in bacilysin biosynthesis.
PubMed:
Dihydrophenylalanine: a prephenate-derived Photorhabdus luminescens antibiotic and intermediate in dihydrostilbene biosynthesis.
PubMed:
An N-terminal protein degradation tag enables robust selection of highly active enzymes.
PubMed:
Crystal structure of prephenate dehydrogenase from Streptococcus mutans.
PubMed:
A "diels-alderase" at last.
PubMed:
Identification of genes in the phenylalanine metabolic pathway by ectopic expression of a MYB transcription factor in tomato fruit.
PubMed:
Complementation of the pha2 yeast mutant suggests functional differences for arogenate dehydratases from Arabidopsis thaliana.
PubMed:
Prephenate decarboxylases: a new prephenate-utilizing enzyme family that performs nonaromatizing decarboxylation en route to diverse secondary metabolites.
PubMed:
Investigation of anticapsin biosynthesis reveals a four-enzyme pathway to tetrahydrotyrosine in Bacillus subtilis.
PubMed:
Mechanism and plasticity of isochorismate pyruvate lyase: a computational study.
PubMed:
Genetic and biochemical identification of the chorismate mutase from Corynebacterium glutamicum.
PubMed:
On-the-path random walk sampling for efficient optimization of minimum free-energy path.
PubMed:
Phenylalanine biosynthesis in Arabidopsis thaliana. Identification and characterization of arogenate dehydratases.
PubMed:
Computer-aided rational design of catalytic antibodies: The 1F7 case.
PubMed:
Vitamin K1 accumulation in tobacco plants overexpressing bacterial genes involved in the biosynthesis of salicylic acid.
PubMed:
Multiple-steering QM-MM calculation of the free energy profile in chorismate mutase.
PubMed:
Investigation of ligand binding and protein dynamics in Bacillus subtilis chorismate mutase by transverse relaxation optimized spectroscopy-nuclear magnetic resonance.
PubMed:
Differential transition-state stabilization in enzyme catalysis: quantum chemical analysis of interactions in the chorismate mutase reaction and prediction of the optimal catalytic field.
PubMed:
How an enzyme surmounts the activation energy barrier.
PubMed:
The near attack conformation approach to the study of the chorismate to prephenate reaction.
PubMed:
Just a near attack conformer for catalysis (chorismate to prephenate rearrangements in water, antibody, enzymes, and their mutants).
PubMed:
Investigation of solvent effects for the Claisen rearrangement of chorismate to prephenate: mechanistic interpretation via near attack conformations.
PubMed:
Comparison of formation of reactive conformers (NACs) for the Claisen rearrangement of chorismate to prephenate in water and in the E. coli mutase: the efficiency of the enzyme catalysis.
PubMed:
Efficiency of lignin biosynthesis: a quantitative analysis.
PubMed:
Understanding the role of active-site residues in chorismate mutase catalysis from molecular-dynamics simulations.
PubMed:
Mapping of chorismate mutase and prephenate dehydrogenase domains in the Escherichia coli T-protein.
PubMed:
The mechanism of catalysis of the chorismate to prephenate reaction by the Escherichia coli mutase enzyme.
PubMed:
HARO7 encodes chorismate mutase of the methylotrophic yeast Hansenula polymorpha and is derepressed upon methanol utilization.
PubMed:
Probing the catalytic mechanism of prephenate dehydratase by site-directed mutagenesis of the Escherichia coli P-protein dehydratase domain.
PubMed:
Identifying groups involved in the binding of prephenate to prephenate dehydrogenase from Escherichia coli.
PubMed:
New insight into the catalytic mechanism of chorismate mutases from structural studies.
PubMed:
Monofunctional chorismate mutase from Bacillus subtilis: FTIR studies and the mechanism of action of the enzyme.
PubMed:
13C NMR studies of the enzyme-product complex of Bacillus subtilis chorismate mutase.
PubMed:
Monofunctional chorismate mutase from Serratia rubidaea: a paradigm system for the three-isozyme gene family of enteric bacteria.
PubMed:
Remnants of an ancient pathway to L-phenylalanine and L-tyrosine in enteric bacteria: evolutionary implications and biotechnological impact.
PubMed:
A single cyclohexadienyl dehydrogenase specifies the prephenate dehydrogenase and arogenate dehydrogenase components of the dual pathways to L-tyrosine in Pseudomonas aeruginosa.
PubMed:
Monofunctional chorismate mutase from Bacillus subtilis: kinetic and 13C NMR studies on the interactions of the enzyme with its ligands.
PubMed:
Catalysis of concerted reactions by antibodies: the Claisen rearrangement.
PubMed:
Synthesis of bacilysin by Bacillus subtilis branches from prephenate of the aromatic amino acid pathway.
PubMed:
A simple spectrophotometric assay for arogenate dehydratase.
PubMed:
Purification of chorismate, prephenate, and arogenate by HPLC.
PubMed:
The postprephenate biochemical pathways to phenylalanine and tyrosine: an overview.
PubMed:
Tyrosine biosynthesis in Sorghum bicolor: isolation and regulatory properties of arogenate dehydrogenase.
PubMed:
Incorporation of chorismic acid and 4-aminobenzoic acid into the 4-hydroxyaniline moiety of N-(gamma-L-glutamyl)-4-hydroxyaniline in Agaricus bisporus.
PubMed:
Mechanisms of enzymatic and acid-catalyzed decarboxylations of prephenate.
PubMed:
Biosynthesis of ketomycin.
PubMed:
Secondary tritium isotope effects as probes of the enzymic and nonenzymic conversion of chorismate to prephenate.
PubMed:
Co-accumulation of prephenate, L-arogenate, and spiro-arogenate in a mutant of Neurospora.
PubMed:
Isolation and structure determination of a novel spiro-gamma-lactam, spiro-arogenate.
PubMed:
[Biosynthesis of phenylalanine and tyrosine in Streptomycetes].
PubMed:
Synthesis and separation of tritium-labeled intermediates of the shikimate pathway.
PubMed:
Chorismate mutase-prephenate dehydrogenase from Escherichia coli. Kinetic mechanism of the prephenate dehydrogenase reaction.
PubMed:
Conversion of phenylalanine into tyrosine by portulaca callus.
PubMed:
Regulation of tyrosine biosynthesis by phenylalanine in anthramycin-producing Streptomyces refuineus.
PubMed:
A novel method for purification of prephenic acid.
PubMed:
Allosteric enzyme-tRNA complexes as regulators of transcription or translation.
PubMed:
Aromatic amino acid biosynthesis in Alcaligenes eutrophus H16. II. The isolation and characterization of mutants auxotrophic for phenylalanine and tyrosine.
PubMed:
THE BIOSYNTHESIS OF PHENYLALANINE AND TYROSINE; ENZYMES CONVERTING CHORISMIC ACID INTO PREPHENIC ACID AND THEIR RELATIONSHIPS TO PREPHENATE DEHYDRATASE AND PREPHENATE DEHYDROGENASE.
PubMed:
PREPARATION OF PREPHENIC ACID AND ITS CONVERSION TO PHENYLALANINE AND TYROSINE BY PLANT ENZYMES.
PubMed:
Aromatic biosynthesis. XVI. Aromatization of prephenic acid to p-hydroxyphenylpyruvic acid, a step in tyrosine biosynthesis in Escherichia coli.
PubMed:
Isolation of prephenic acid from Neurospora.