prephenic acid
2,5-cyclohexadiene-1-propanoic acid, 1-carboxy-4-hydroxy-alpha-oxo-
 
Notes:
Prephenic acid, more commonly known by its anionic form prephenate, is an intermediate in the biosynthesis of the aromatic amino acids phenylalanine and tyrosine. [HMDB]
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CAS Number: 126-49-8Picture of molecule3D/inchi
FDA UNII: Z66B98Z97I
Nikkaji Web: J38.009A
XlogP3-AA: -0.50 (est)
Molecular Weight: 226.18490000
Formula: C10 H10 O6
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 1028
National Institute of Allergy and Infectious Diseases: Data
 1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
Chemidplus: 0000126498
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References:
 1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 1028
Pubchem (cas): 126-49-8
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
Golm Metabolome Database: Search
Metabolomics Database: Search
KEGG (GenomeNet): C00254
HMDB (The Human Metabolome Database): HMDB12283
FooDB: FDB028914
YMDB (Yeast Metabolome Database): YMDB00324
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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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-
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Articles:
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.
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