Chorismic acid. Medical search

A cyclohexadiene carboxylic acid derived from SHIKIMIC ACID and a precursor for the biosynthesis of UBIQUINONE and the AROMATIC AMINO ACIDS.

Works containing information articles on subjects in every field of knowledge, usually arranged in alphabetical order, or a similar work limited to a special field or subject. (From The ALA Glossary of Library and Information Science, 1983)

Antibiotic pigment produced by Pseudomonas aeruginosa.

Organic compounds containing the carboxy group (-COOH). This group of compounds includes amino acids and fatty acids. Carboxylic acids can be saturated, unsaturated, or aromatic.

Tricyclic antidepressant similar in action and side effects to IMIPRAMINE. It may produce excitation.

Enzymes that catalyze the shifting of a carbon-carbon double bond from one position to another within the same molecule. EC 5.3.3.

The five-carbon building blocks of TERPENES that derive from MEVALONIC ACID or deoxyxylulose phosphate.

Derivatives of the dimethylisoalloxazine (7,8-dimethylbenzo[g]pteridine-2,4(3H,10H)-dione) skeleton. Flavin derivatives serve an electron transfer function as ENZYME COFACTORS in FLAVOPROTEINS.

Enzymes of the isomerase class that catalyze the transfer of acyl-, phospho-, amino- or other groups from one position within a molecule to another. EC 5.4.

A somewhat heterogeneous class of enzymes that catalyze the transfer of alkyl or related groups (excluding methyl groups). EC 2.5.

An autosomal recessive form of CHONDRODYSPLASIA PUNCTATA characterized by defective plasmalogen biosynthesis and impaired peroxisomes. Patients have shortened proximal limbs and severely disturbed endochondral bone formation. The metabolic defects associated with the impaired peroxisomes are present only in the rhizomelic form of chondrodysplasia punctata. (From Scriver et al, Metabolic Basis of Inherited Disease, 6th ed, p1497)

Phospholipids which have an alcohol moiety in ethereal linkage with a saturated or unsaturated aliphatic alcohol. They are usually derivatives of phosphoglycerols or phosphatidates. The other two alcohol groups of the glycerol backbone are usually in ester linkage. These compounds are widely distributed in animal tissues.

The systematic identification and quantitation of all the metabolic products of a cell, tissue, organ, or organism under varying conditions. The METABOLOME of a cell or organism is a dynamic collection of metabolites which represent its net response to current conditions.

Strains of Escherichia coli that preferentially grow and persist within the urinary tract. They exhibit certain virulence factors and strategies that cause urinary tract infections.

Inflammatory responses of the epithelium of the URINARY TRACT to microbial invasions. They are often bacterial infections with associated BACTERIURIA and PYURIA.

Proteins obtained from ESCHERICHIA COLI.

A species of gram-negative, facultatively anaerobic, rod-shaped bacteria (GRAM-NEGATIVE FACULTATIVELY ANAEROBIC RODS) commonly found in the lower part of the intestine of warm-blooded animals. It is usually nonpathogenic, but some strains are known to produce DIARRHEA and pyogenic infections. Pathogenic strains (virotypes) are classified by their specific pathogenic mechanisms such as toxins (ENTEROTOXIGENIC ESCHERICHIA COLI), etc.

Infections with bacteria of the species ESCHERICHIA COLI.

An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers.

A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.

Enzymes that catalyze the cleavage of a phosphorus-oxygen bond by means other than hydrolysis or oxidation. EC 4.6.

An isomerase that catalyzes the conversion of chorismic acid to prephenic acid. EC 5.4.99.5.

The rate dynamics in chemical or physical systems.

A sex-linked recessive disorder affecting multiple systems including the EYE, the NERVOUS SYSTEM, and the KIDNEY. Clinical features include congenital CATARACT; MENTAL RETARDATION; and renal tubular dysfunction (FANCONI SYNDROME; RENAL TUBULAR ACIDOSIS; X-LINKED HYPOPHOSPHATEMIA or vitamin-D-resistant rickets) and SCOLIOSIS. This condition is due to a deficiency of phosphatidylinositol 4,5-bisphosphate-5-phosphatase leading to defects in PHOSPHATIDYLINOSITOL metabolism and INOSITOL signaling pathway. (from Menkes, Textbook of Child Neurology, 5th ed, p60; Am J Hum Genet 1997 Jun;60(6):1384-8)

An enzyme system that catalyzes the fixing of nitrogen in soil bacteria and blue-green algae (CYANOBACTERIA). EC 1.18.6.1.

Process of shifting publicly controlled services and/or facilities to the private sector.

A non-steroidal ESTROGEN generated when soybean products are metabolized by certain bacteria in the intestines.

The number of CELLS of a specific kind, usually measured per unit volume or area of sample.

Low-molecular-weight compounds produced by microorganisms that aid in the transport and sequestration of ferric iron. (The Encyclopedia of Molecular Biology, 1994)

Number of individuals in a population relative to space.

A phenomenon where microorganisms communicate and coordinate their behavior by the accumulation of signaling molecules. A reaction occurs when a substance accumulates to a sufficient concentration. This is most commonly seen in bacteria.

Any liquid or solid preparation made specifically for the growth, storage, or transport of microorganisms or other types of cells. The variety of media that exist allow for the culturing of specific microorganisms and cell types, such as differential media, selective media, test media, and defined media. Solid media consist of liquid media that have been solidified with an agent such as AGAR or GELATIN.

A species of gram-negative, facultatively anaerobic, rod-shaped bacteria that is extremely pathogenic and causes severe dysentery. Infection with this organism often leads to ulceration of the intestinal epithelium.

A species of gram-negative bacteria (currently incertae sedis) causing multisystem disease in CATTLE.

Amino acids containing an aromatic side chain.

Potentially pathogenic bacteria found in nasal membranes, skin, hair follicles, and perineum of warm-blooded animals. They may cause a wide range of infections and intoxications.

An enzyme of the shikimate pathway of AROMATIC AMINO ACID biosynthesis, it generates 5-enolpyruvylshikimate 3-phosphate and ORTHOPHOSPHATE from PHOSPHOENOLPYRUVATE and shikimate-3-phosphate. The shikimate pathway is present in BACTERIA and PLANTS but not in MAMMALS.

A species of bacteria that causes ANTHRAX in humans and animals.

A species of gram-negative, aerobic bacteria primarily found in purulent venereal discharges. It is the causative agent of GONORRHEA.

Electric power supply devices which convert biological energy, such as chemical energy of metabolism or mechanical energy of periodic movements, into electrical energy.

The physical effects involving the presence of electric charges at rest and in motion.

Forms of energy that are constantly and rapidly renewed by natural processes such as solar, ocean wave, and wind energy. (from McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed)

Electric conductors through which electric currents enter or leave a medium, whether it be an electrolytic solution, solid, molten mass, gas, or vacuum.

A species of gram-negative, aerobic, rod-shaped bacteria commonly isolated from clinical specimens (wound, burn, and urinary tract infections). It is also found widely distributed in soil and water. P. aeruginosa is a major agent of nosocomial infection.

The process by which ELECTRONS are transported from a reduced substrate to molecular OXYGEN. (From Bennington, Saunders Dictionary and Encyclopedia of Laboratory Medicine and Technology, 1984, p270)

Nanometer-scale wires made of materials that conduct electricity. They can be coated with molecules such as antibodies that will bind to proteins and other substances.

Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM.

MYCOBACTERIUM infections of the lung.

Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.

A species of gram-positive, aerobic bacteria that produces TUBERCULOSIS in humans, other primates, CATTLE; DOGS; and some other animals which have contact with humans. Growth tends to be in serpentine, cordlike masses in which the bacilli show a parallel orientation.

Tuberculosis resistant to ISONIAZID and RIFAMPIN and at least three of the six main classes of second-line drugs (AMINOGLYCOSIDES; polypeptide agents; FLUOROQUINOLONES; THIOAMIDES; CYCLOSERINE; and PARA-AMINOSALICYLIC ACID) as defined by the CDC.

Acquiring information from a patient on past medical conditions and treatments.

The ability of bacteria to resist or to become tolerant to several structurally and functionally distinct drugs simultaneously. This resistance may be acquired through gene mutation or foreign DNA in transmissible plasmids (R FACTORS).

The aroC gene of Aspergillus nidulans codes for a monofunctional, allosterically regulated chorismate mutase. (1/70)

The cDNA and the chromosomal locus of the aroC gene of Aspergillus nidulans were cloned and is the first representative of a filamentous fungal gene encoding chorismate mutase (EC 5.4.99.5), the enzyme at the first branch point of aromatic amino acid biosynthesis. The aroC gene complements the Saccharomyces cerevisiae aro7Delta as well as the A. nidulans aroC mutation. The gene consists of three exons interrupted by two short intron sequences. The expressed mRNA is 0.96 kilobases in length and aroC expression is not regulated on the transcriptional level under amino acid starvation conditions. aroC encodes a monofunctional polypeptide of 268 amino acids. Purification of this 30-kDa enzyme allowed determination of its kinetic parameters (k(cat) = 82 s(-1), n(H) = 1. 56, [S](0.5) = 2.3 mM), varying pH dependence of catalytic activity in different regulatory states, and an acidic pI value of 4.7. Tryptophan acts as heterotropic activator and tyrosine as negative acting, heterotropic feedback-inhibitor with a K(i) of 2.8 microM. Immunological data, homology modeling, as well as electron microscopy studies, indicate that this chorismate mutase has a dimeric structure like the S. cerevisiae enzyme. Site-directed mutagenesis of a crucial residue in loop220s (Asp(233)) revealed differences concerning the intramolecular signal transduction for allosteric regulation of enzymatic activity. (+info)

Characterization of hydroxylaminobenzene mutase from pNBZ139 cloned from Pseudomonas pseudoalcaligenes JS45. A highly associated SDS-stable enzyme catalyzing an intramolecular transfer of hydroxy groups. (2/70)

Hydroxylaminobenzene mutase is the enzyme that converts intermediates formed during initial steps in the degradation of nitrobenzene to a novel ring-fission lower pathway in Pseudomonas pseudoalcaligenes JS45. The mutase catalyzes a rearrangement of hydroxylaminobenzene to 2-aminophenol. The mechanism of the reactions and the properties of the enzymes are unknown. In crude extracts, the hydroxylaminobenzene mutase was stable at SDS concentrations as high as 2%. A procedure including Hitrap-SP, Hitrap-Q and Cu(II)-chelating chromatography was used to partially purify the enzyme from an Escherichia coli clone. The partially purified enzyme was eluted in the void volume of a Superose-12 gel-filtration column even in the presence of 0.05% SDS in 25 mM Tris/HCl buffer, which indicated that it was highly associated. When the enzymatic conversion of hydroxylaminobenzene to 2-aminophenol was carried out in 18O-labeled water, the product did not contain 18O, as determined by GC-MS. The results indicate that the reaction proceeded by intramolecular transfer of the hydroxy group from the nitrogen to the C-2 position of the ring. The mechanism is clearly different from the intermolecular transfer of the hydroxy group in the non-enzymatic Bamberger rearrangement of hydroxylaminobenzene to 4-aminophenol and in the enzymatic hydroxymutation of chorismate to isochorismate. (+info)

Archaeal shikimate kinase, a new member of the GHMP-kinase family. (3/70)

Shikimate kinase (EC 2.7.1.71) is a committed enzyme in the seven-step biosynthesis of chorismate, a major precursor of aromatic amino acids and many other aromatic compounds. Genes for all enzymes of the chorismate pathway except shikimate kinase are found in archaeal genomes by sequence homology to their bacterial counterparts. In this study, a conserved archaeal gene (gi1500322 in Methanococcus jannaschii) was identified as the best candidate for the missing shikimate kinase gene by the analysis of chromosomal clustering of chorismate biosynthetic genes. The encoded hypothetical protein, with no sequence similarity to bacterial and eukaryotic shikimate kinases, is distantly related to homoserine kinases (EC 2.7.1.39) of the GHMP-kinase superfamily. The latter functionality in M. jannaschii is assigned to another gene (gi591748), in agreement with sequence similarity and chromosomal clustering analysis. Both archaeal proteins, overexpressed in Escherichia coli and purified to homogeneity, displayed activity of the predicted type, with steady-state kinetic parameters similar to those of the corresponding bacterial kinases: K(m,shikimate) = 414 +/- 33 microM, K(m,ATP) = 48 +/- 4 microM, and k(cat) = 57 +/- 2 s(-1) for the predicted shikimate kinase and K(m,homoserine) = 188 +/- 37 microM, K(m,ATP) = 101 +/- 7 microM, and k(cat) = 28 +/- 1 s(-1) for the homoserine kinase. No overlapping activity could be detected between shikimate kinase and homoserine kinase, both revealing a >1,000-fold preference for their own specific substrates. The case of archaeal shikimate kinase illustrates the efficacy of techniques based on reconstruction of metabolism from genomic data and analysis of gene clustering on chromosomes in finding missing genes. (+info)

Essential PchG-dependent reduction in pyochelin biosynthesis of Pseudomonas aeruginosa. (4/70)

The biosynthetic genes pchDCBA and pchEF, which are known to be required for the formation of the siderophore pyochelin and its precursors salicylate and dihydroaeruginoate (Dha), are clustered with the pchR regulatory gene on the chromosome of Pseudomonas aeruginosa. The 4.6-kb region located downstream of the pchEF genes was found to contain three additional, contiguous genes, pchG, pchH, and pchI, probably forming a pchEFGHI operon. The deduced amino acid sequences of PchH and PchI are similar to those of ATP binding cassette transport proteins with an export function. PchG is a homolog of the Yersinia pestis and Y. enterocolitica proteins YbtU and Irp3, which are involved in the biosynthesis of yersiniabactin. A null mutation in pchG abolished pyochelin formation, whereas mutations in pchH and pchI did not affect the amounts of salicylate, Dha, and pyochelin produced. The pyochelin biosynthetic genes were expressed from a vector promoter, uncoupling them from Fur-mediated repression by iron and PchR-dependent induction by pyochelin. In a P. aeruginosa mutant lacking the entire pyochelin biosynthetic gene cluster, the expressed pchDCBA and pchEFG genes were sufficient for salicylate, Dha, and pyochelin production. Pyochelin formation was also obtained in the heterologous host Escherichia coli expressing pchDCBA and pchEFG together with the E. coli entD gene, which provides a phosphopantetheinyl transferase necessary for PchE and PchF activation. The PchG protein was purified and used in combination with PchD and phosphopantetheinylated PchE and PchF in vitro to produce pyochelin from salicylate, L-cysteine, ATP, NADPH, and S-adenosylmethionine. Based on this assay, a reductase function was attributed to PchG. In summary, this study completes the identification of the biosynthetic genes required for pyochelin formation from chorismate in P. aeruginosa. (+info)

The structures of anthranilate synthase of Serratia marcescens crystallized in the presence of (i) its substrates, chorismate and glutamine, and a product, glutamate, and (ii) its end-product inhibitor, L-tryptophan. (5/70)

The crystal structure of anthranilate synthase (AS) from Serratia marcescens, a mesophilic bacterium, has been solved in the presence of its substrates, chorismate and glutamine, and one product, glutamate, at 1.95 A, and with its bound feedback inhibitor, tryptophan, at 2.4 A. In comparison with the AS structure from the hyperthermophile Sulfolobus solfataricus, the S. marcescens structure shows similar subunit structures but a markedly different oligomeric organization. One crystal form of the S. marcescens enzyme displays a bound pyruvate as well as a putative anthranilate (the nitrogen group is ambiguous) in the TrpE subunit. It also confirms the presence of a covalently bound glutamyl thioester intermediate in the TrpG subunit. The tryptophan-bound form reveals that the inhibitor binds at a site distinct from that of the substrate, chorismate. Bound tryptophan appears to prevent chorismate binding by a demonstrable conformational effect, and the structure reveals how occupancy of only one of the two feedback inhibition sites can immobilize the catalytic activity of both TrpE subunits. The presence of effectors in the structure provides a view of the locations of some of the amino acid residues in the active sites. Our findings are discussed in terms of the previously described AS structure of S. solfataricus, mutational data obtained from enteric bacteria, and the enzyme's mechanism of action. (+info)

Microbial origin of plant-type 2-keto-3-deoxy-D-arabino-heptulosonate 7-phosphate synthases, exemplified by the chorismate- and tryptophan-regulated enzyme from Xanthomonas campestris. (6/70)

Enzymes performing the initial reaction of aromatic amino acid biosynthesis, 2-keto-3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthases, exist as two distinct homology classes. The three classic Escherichia coli paralogs are AroA(I) proteins, but many members of the Bacteria possess the AroA(II) class of enzyme, sometimes in combination with AroA(I) proteins. AroA(II) DAHP synthases until now have been shown to be specifically dedicated to secondary metabolism (e.g., formation of ansamycin antibiotics or phenazine pigment). In contrast, here we show that the Xanthomonas campestris AroA(II) protein functions as the sole DAHP synthase supporting aromatic amino acid biosynthesis. X. campestris AroA(II) was cloned in E. coli by functional complementation, and genes corresponding to two possible translation starts were expressed. We developed a 1-day partial purification method (>99%) for the unstable protein. The recombinant AroA(II) protein was found to be subject to an allosteric pattern of sequential feedback inhibition in which chorismate is the prime allosteric effector. L-Tryptophan was found to be a minor feedback inhibitor. An N-terminal region of 111 amino acids may be located in the periplasm since a probable inner membrane-spanning region is predicted. Unlike chloroplast-localized AroA(II) of higher plants, X. campestris AroA(II) was not hysteretically activated by dithiols. Compared to plant AroA(II) proteins, differences in divalent metal activation were also observed. Phylogenetic tree analysis shows that AroA(II) originated within the Bacteria domain, and it seems probable that higher-plant plastids acquired AroA(II) from a gram-negative bacterium via endosymbiosis. The X. campestris AroA(II) protein is suggested to exemplify a case of analog displacement whereby an ancestral aroA(I) species was discarded, with the aroA(II) replacement providing an alternative pattern of allosteric control. Three subgroups of AroA(II) proteins can be recognized: a large, central group containing the plant enzymes and that from X. campestris, one defined by a three-residue deletion near the conserved KPRS motif, and one possessing a larger deletion further downstream. (+info)

The emerging periplasm-localized subclass of AroQ chorismate mutases, exemplified by those from Salmonella typhimurium and Pseudomonas aeruginosa. (7/70)

BACKGROUND: Chorismate mutases of the AroQ homology class are widespread in the Bacteria and the Archaea. Many of these exist as domains that are fused with other aromatic-pathway catalytic domains. Among the monofunctional AroQ proteins, that from Erwinia herbicola was previously shown to have a cleavable signal peptide and located in the periplasmic compartment. Whether or not this might be unique to E. herbicola was unknown. RESULTS: The gene coding for the AroQ protein was cloned from Salmonella typhimurium, and the AroQ protein purified from both S. typhimurium and Pseudomonas aeruginosa was shown to have a periplasmic location. The periplasmic chorismate mutases (denoted *AroQ) are shown to be a distinct subclass of AroQ, being about twice the size of cytoplasmic AroQ proteins. The increased size is due to a carboxy-terminal extension of unknown function. In addition, a so-far novel aromatic aminotransferase was shown to be present in the periplasm of P. aeruginosa. CONCLUSIONS: Our analysis has detected a number of additional *aroQ genes. The joint presence of *AroQ, cyclohexadienyl dehydratase and aromatic aminotransferase in the periplasmic compartment of P. aeruginosa comprises a complete chorismate-to-phenylalanine pathway and accounts for the "hidden overflow pathway" to phenylalanine described previously. (+info)

Clustering of isochorismate synthase genes menF and entC and channeling of isochorismate in Escherichia coli. (8/70)

There are two isochorismate synthase genes entC and menF in Escherichia coli. They encode enzymes (isochorismate synthase, EC 5.4.99.6) which reversibly synthesize isochorismic acid from chorismic acid. The genes share a 24.2% identity but are differently regulated. Activity of the MenF isochorismate synthase is significantly increased under anaerobic conditions whereas the activity of the EntC isochorismate synthase is greatly stimulated during growth in an iron deficient medium. Isochorismic acid synthesized by EntC is mainly channeled into enterobactin synthesis whereas isochorismic acid synthesized by MenF is mainly channeled into menaquinone synthesis. When menF or entC were separately placed onto overexpression plasmids and the plasmids introduced into a menF(-)/entC(-) double mutant in two separate experiments, the isochorismate formed was fed into both, the menaquinone and the enterobactin pathway. Moreover, in spite of a high isochorismate synthase activity menaquinone and enterobactin formation were not fully restored, indicating that isochorismate was lost by diffusion. Thus, under these conditions channeling was not observed. We conclude that in E. coli the chromosomal position of both menF and entC in their respective clusters is a prerequisite for channeling of isochorismate in both pathways. (+info)

Chorismic acid is the precursor of pyocyanin. shikimic acid → chorismic acid → phenazine-1-carboxylic acid → 5-methylphenazine- ... In this reaction the enzyme PhzE catalyzes the loss of the hydroxyl group from C4 of Chorismic Acid as well as the transfer of ... Biosynthesis can be impaired by disrupting the aro pathway which is responsible for the synthesis of chorismic acid from ... 6-carboxylic acid (THPCA). In the final step of phenazine-1-carboxylic acid synthesis the enzyme PhzG catalyzes the oxidation ...

https://en.wikipedia.org/wiki/Pyocyanin

DHB is synthesized from chorismic acid by a series of enzymes: VibA, VibB, and VibC. DHB is linked to NSPD by VibE, VibB and ... The components of vibriobactin are three 2,3-dihydroxybenzoic acid (DHB), two threonine (Thr), and one norspermidine (NSPD). ...

https://en.wikipedia.org/wiki/Vibriobactin

... biosynthesis branches off the shikimic acid pathway at a point subsequent to chorismic acid. Two molecules of this ... Sulfuric acid dissolves it, forming a deep-red solution. Classically phenazine are prepared by the reaction of nitrobenzene and ... When heated with concentrated hydrochloric acid the amino group is replaced by the hydroxyl group and the phenolic eurhodols ... It dissolves in concentrated sulfuric acid with a yellowish-green fluorescence. The rhodamines, which are closely related to ...

https://en.wikipedia.org/wiki/Phenazine

... chorismic acid. Tryptophan is converted to indole-3-acetaldoxime (IAOx) by cytochrome p450 enzymes (the redundant CYP92B3 and ... The biosynthesis of glucobrassicin begins with tryptophan produced through several steps from the Shikimic acid pathway ...

https://en.wikipedia.org/wiki/Glucobrassicin

Shikimate is converted into chorismic acid, which is further converted into 2-succinylbenzoic acid through a TPP-dependent ... After 2-succinylbenzoic acid has been produced, a cyclization, a prenylation, a methylation, and an oxidation occur which ... Mechanistically, it is proposed that the phenylboronic acid promotes a cyclization that is followed by a Diels-Alder reaction ...

https://en.wikipedia.org/wiki/Rubicordifolin

Chorismic acid, an aromatic amino acid precursor, is converted to 2,3-dihydroxybenzoic acid (DHB) by a series of enzymes, EntA ... These initial studies established the structure and its relationship to 2,3-dihydroxybenzoic acid. Dertz EA, Xu J, Stintzi A, ... O'Brien IG, Cox GB, Gibson F (March 1970). "Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine ...

https://en.wikipedia.org/wiki/Enterobactin

The starter unit, DHCHC from the chorismic acid is formed by fkbO enzyme and loaded onto CoA-ligase domain (CoL). Then, it ... After the last step (module 10) of PKS 1, one molecule of L-pipecolic acid formed from L-lysine and catalyzed through fkbL ... The process of L-pipecolic acid synthesis is NRPS enforced by fkbP enzyme. After synthesizing the entire subunits, the molecule ... The fundamental units for biosynthesis are following: one molecule of 4,5-dihydroxycyclohex-1-enecarboxylic acid (DHCHC) as a ...

https://en.wikipedia.org/wiki/Tacrolimus

The molecular formula C10H10O6 (molar mass: 226.18 g/mol, exact mass: 226.0477 u) may refer to: Chorismic acid Prephenic acid ...

https://en.wikipedia.org/wiki/C10H10O6

... acid chlorogenic acid chorismic acid dicyclomine quinic acid shikimic acid tranexamic acid Quinic acid Shikimic acid Chorismic ... Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride ... Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H. It is the carboxylic acid of cyclohexane. It is ... Cyclohexanecarboxylic acid is a precursor to the nylon-6 precursor caprolactam via its reaction with nitrosylsulfuric acid. It ...

https://en.wikipedia.org/wiki/Cyclohexanecarboxylic_acid

The name chorismic acid derives from a classical Greek word χωρίζω meaning "to separate", because the compound plays a role as ... Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and ... 3-Dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis The plant hormone salicylic acid Many alkaloids and other ... C10H10O6 Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001). "Isochorismate synthase is required to synthesize salicylic acid ...

https://en.wikipedia.org/wiki/Chorismic_acid

... undergoes five further enzymatic steps in the remainder of the shikimate pathway to chorismic acid, a ... 3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3- ... 3-Dehydroquinate goes through beta oxidation, similar to fatty acids. Then, this compound (6-oxo-3-dehydro-quinate) is ... It has the same structure as quinic acid, which is found in coffee, but the C-3 hydroxyl is oxidized to a ketone group. ...

https://en.wikipedia.org/wiki/3-Dehydroquinic_acid

The enzymic synthesis of chorismic and prephenic acids from 3-enolpyruvylshikimic acid 5-phosphate". J. Biol. Chem. 242: 82-90 ...

https://sr.wikipedia.org/wiki/Horizmatna_sintaza

https://en.wikipedia.org/wiki/Chorismic_acid

Chorismic acid from Enterobacter aerogenes ,=80%; CAS No.: 617-12-9; Synonyms: trans-3-([1-Carboxyethenyl]oxy)-4-hydroxy-1,5- ... Chorismic acid from Enterobacter aerogenes ≥80% Synonym: trans-. 3-. ([1-. Carboxyethenyl]. oxy). -. 4-. hydroxy-. 1,5- ... Chorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate ... Building Blocks, C10, Carbonyl Compounds, Carboxylic Acids, Chemical Synthesis, Organic Building Blocks ...

https://www.sigmaaldrich.com/catalog/product/ALDRICH/C1761?lang=en®ion=US

Chorismic Acid. Chorismic Acid bmse000075 - Data bmse000998 - Data bmst000056 - Theory Chorismic Acid synonyms. 1,5- ... Cyclohexadiene-1-carboxylic acid, 3-((1-carboxyethenyl)oxy)-4-hydroxy-, (3R-trans)-; CHORISMIC ACID; Chorismate; Chorismic acid ... A Repository for Data from NMR Spectroscopy on Proteins, Peptides, Nucleic Acids, and other Biomolecules Member of ... 3R,4R)-3-(1-carboxyethenoxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid. ...

http://bmrb.wisc.edu/metabolomics/mol_summary/?molName=Chorismic+acid

Anthranilic acid was first obtained by base-induced degradation of indigo. Anthranilic acid is biosynthesized from chorismic ... tolfenamic acid, flufenamic acid, and meclofenamic acid are derived from fenamic acid or anthranilic acid and are called " ... Fenamic acid is a derivative of anthranilic acid, which in turn is a nitrogen isostere of salicylic acid, which is the active ... Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a ...

https://en.wikipedia.org/wiki/Anthranilic_acid

Chorismic acid is the precursor of pyocyanin. shikimic acid → chorismic acid → phenazine-1-carboxylic acid → 5-methylphenazine- ... of the hydroxyl group from C4 of Chorismic Acid as well as the transfer of an amine group from glutamine to form glutamic acid ... Biosynthesis can be impaired by disrupting the aro pathway which is responsible for the synthesis of chorismic acid from ... 6-carboxylic acid (THPCA).[20] In the final step of phenazine-1-carboxylic acid synthesis the enzyme PhzG catalyzes the ...

https://en.wikipedia.org/wiki/Pyocyanin

In these enzymes, the flavin plays either a direct role in acid/base reactions or as a nucleophile or electrophile. In addition ... Hill, R.K.; Newkome, G.R. Stereochemistry of chorismic acid biosynthesis. J. Am. Chem. Soc 1969, 91, 5893-5894. [Google Scholar ... acting as either an acid or a base, or functioning as both an acid and a base [44]. A role for the reduced FMN in charge ... such as both an acid and a base, in electron transfer and acid/base reactions, and as a molecular scaffold forming a covalent ...

http://www.mdpi.com/1422-0067/13/11/14219/htm

... model UPEC strain UTI89 produces three siderophores derived from chorismic acid precursors. Isogenic mutants disrupting ...

https://www.ncbi.nlm.nih.gov/pubmed/25861985

Interestingly, the yersiniabactin and salmochelin biosynthetic pathways converge at chorismic acid, where each pathway uses ... Figure 6. Biosynthesis of siderophores associated with recurrent UTI depends on chorismic acid utilization. ... formic acid) was held constant at 95% and solvent B (80% acetonitrile in 0.1% formic acid) was held constant at 5% for 5 ... formic acid in 10% acetonitrile. Siderophores were eluted following application of 2 mL of 0.1% formic acid in 80% acetonitrile ...

http://journals.plos.org/plospathogens/article?id=10.1371/journal.ppat.1000305

Chorismic acid, a key metabolite in modification of tRNA. J. Bacteriol. 172:252-259. ... Biological function of 2-thiouridine in Escherichia coli glutamic acid transfer ribonucleic acid. Biochemistry 12:4331-4337. ... acetic acid in water and then destained overnight at room temperature in 5% (vol/vol) methanol and 10% (vol/vol) acetic acid in ... Amino acid residues identical to those in the S. cerevisiae sequence are shaded. GenBank accession numbers are as follows: S. ...

https://mcb.asm.org/content/23/24/9283?ijkey=01b906d6b8ceca31479f83cbb12089b7f4c3a469&keytype2=tf_ipsecsha

The enzymic synthesis of chorismic and prephenic acids from 3-enolpyruvylshikimic acid 5-phosphate". J. Biol. Chem. 242: 82-90 ...

https://sr.wikipedia.org/wiki/Horizmatna_sintaza

SA is synthesised from chorismic acid, derived from the shikimic acid pathway, and that SA biosynthesis occurs in the plastid [ ... Salicylic acid (SA; 2-hydroxybenzoic acid) is an important plant hormone [1]. Although it has been most thoroughly studied with ... Efficient in vivo synthesis and rapid purification of chorismic acid using an engineered Escherichia coli strain ... The important plant hormone salicylic acid (SA; 2-hydroxybenzoic acid) regulates several key plant responses including, most ...

https://portlandpress.com/biochemj/article/474/10/1579/49413/The-biochemical-properties-of-the-two-Arabidopsis

... which is produced from chorismic acid. PCA is further modified in pyocyanin (PYO), 1-hydroxyphenazine (1-HP), or phenazine-1- ... The acetic acid was removed to clean 96 well plates and the absorbance at 560 nm was measured (Thermo Labsystems Multiskan EX). ... The biofilms were destained by the addition of 130 μl of 30% acetic acid in water to each well for 20 min under agitation at ... Wang Y. et al. Phenazine-1-carboxylic acid promotes bacterial biofilm development via ferrous iron acquisition. J. Bacteriol. ...

http://pubmedcentralcanada.ca/pmcc/articles/PMC5389140/

Anthranilic acid is produced from chorismic acid and is further converted to the aromatic amino acid Trp. After herbivore ... AA, Anthranilic acid; BA, benzoic acid; SA, salicylic acid; IAA, indole-3-acetic acid; IPA, indole-3-propionic acid; IBA, ... indole-3-butyric acid; CinA, cinnamic acid; CouA, o-coumaric acid; JA, jasmonic acid; 3ABA, 3-aminobenzoic acid; 4ABA, 4- ... S1). To find amino acids responsible for substrate specificity of AAMT1, we looked for active site amino acids that are highly ...

http://www.plantphysiol.org/content/153/4/1795.full

One such nutritional limitation is the availability of aromatic amino acids (AAAs) as animals lack the enzymes to synthesize ... One such nutritional limitation is the availability of aromatic amino acids (AAAs) as animals lack the enzymes to synthesize ... Chorismic acid derived from the shikimic acid pathway is a key intermediate in producing Trp, phenylalanine (Phe), and tyrosine ... Bilkay IS, Karakoç S, Aksoz N. Indole-3-acetic acid and gibberellic acid production in Aspergillus niger. Turk J Biol (2010) 34 ...

https://www.frontiersin.org/articles/10.3389/fimmu.2017.01996/full

This mutant is defective in conversion of chorismic acid to the aromatic substrate for Ent synthesis, whereas EntF is required ... The pH of the culture fluid was then reduced to about 2.5 with 12 N hydrochloric acid, and the siderophores were extracted with ... The low-iron minimal medium for our experiments consisted of 50 mM 3-(N-morpholino)propanesulfonic acid (MOPS; pH 7), 50 mM ...

https://jb.asm.org/content/197/13/2122

Among these, salicylic acid signaling is an important pathway because of its ability to trigger plant cell death. As biotrophic ... Here we review the strategies prokaryotic pathogens have developed to target salicylic acid biosynthesis and signaling, and ... Here we review the strategies prokaryotic pathogens have developed to target salicylic acid biosynthesis and signaling, and ... they have evolved efficient strategies to downregulate salicylic acid signaling by virulence effectors, which can be proteins ...

https://www.frontiersin.org/articles/10.3389/fpls.2015.00349/full

I have published on such topics as pyridoxal phosphate (vitamin B6) enzymes, chorismic acid metabolizing enzymes and bio- ...

https://www.roundtablegroup.com/expert-witness-field/chemistry/

Klebsiella pneumoniae 62-1 excretes 4-hydroxybenzoic acid instead of chorismic acid. The recombinant strain can be used to ... Schmid HV, Zenk MH (1971) p-hydroxybenzoic acid and mevalonic acid as precursors of the plant naphthoquinone alkannin. ... Kaneda T, Obata H, Tokumoto M (1993) Aromatization of 4-oxocylohexanecarboxylic acid to 4-hydroxybenzoic acid by two ... Synthesis of isotopically labelled monomers and polymers of 4-hydroxybenzoic acid and 6-hydroxy-2-naphthoic acid. Makromol Chem ...

https://link.springer.com/article/10.1007%2FBF00166913

The enzymic synthesis of chorismic and prephenic acids from 3-enolpyruvylshikimic acid 5-phosphate. J. Biol. Chem. 242 (1967) ... lupinic acid. zeatin. O-acetyl-L-serine = (2S)-3-acetyloxy-2-aminopropanoic acid. Other name(s): β-(9-cytokinin)-alanine ... 2) 2 ATP + 2 cob(II)yrinic acid a,c-diamide + a reduced flavoprotein = 2 triphosphate + 2 adenosylcob(III)yrinic acid a,c- ... 2c) 2 ATP + 2 [corrinoid adenosyltransferase]-cob(I)yrinic acid a,c-diamide = 2 triphosphate + 2 adenosylcob(III)yrinic acid a, ...

https://www.qmul.ac.uk/sbcs/iubmb/enzyme/EC2/05.html

... coli controls the biosynthesis of tryptophan in the cell from the initial precursor chorismic acid. This operon contains genes ... When the amino acid is not there, the repressor moves away from the operator and RNA synthesis continues.(Lumen, 2007) ... The genetic code describes the relationship between the sequence of base pairs in a gene and the corresponding amino acid ... molecule to a sequence of amino acids during protein synthesis. ... Transcription will occur at a lower rate.When an amino acid ...

https://www.powtoon.com/online-presentation/dPnlUJTVjaZ/?mode=movie

... directly from chorismic acid or via anthranilic acid (data not shown). However, when CA or BA was added back to leaves treated ... arachidonic acid. AIP. 2-aminoindan-2-phosphonic acid. BA. benzoic acid. CA. cinnamic acid. PAL. Phe ammonia-lyase. SA. ... 1995) Arachidonic acid induces local but not systemic synthesis of salicylic acid and confers systemic resistance in potato ... 1962) Conversion in plants of benzoic acid to salicylic acid and its β-d-glucoside. Nature 196:491. ...

http://www.plantphysiol.org/content/117/3/1095.full

... for the observed auxotrophic phenotype is one of those required for the synthesis of shikimic acid and chorismic acid (2). By ... Requirement of p-aminobenzoic acid (PABA), a precursor of folic acid that is not synthesized by mammals, has been singled out ... The aro mutants are auxotrophs for aromatic amino acids, PABA (a precursor of folic acid), and DHB (a precursor for ubiquinone ... which codes for the 3-phosphoshikimate 1-carboxyvinyltransferase of the chorismic acid biosynthesis pathway (39). The ...

https://iai.asm.org/content/74/6/3498

Phenazines are synthesized from chorismic acid (19, 20) via the intermediate phenazine-1-carboxylic acid (PCA), which is ... It is widely accepted that P. aeruginosa prefers organic acids and amino acids to glucose in a sequential hierarchy (45, 46). ... Phenazine-1-carboxylic acid promotes bacterial biofilm development via ferrous iron acquisition. J Bacteriol 193:3606-3617. doi ... For analysis of carbon source consumption and secreted metabolites, sample supernatants were separated on an organic acid resin ...

https://aem.asm.org/content/82/16/5026

... also known as the shikimic acid pathway, in which chorismic acid is synthesized. The latter compound is the synthetic precursor ... also known as the shikimic acid pathway, in which chorismic acid is synthesized. The latter compound is the synthetic precursor ... effort has been focused on the discovery of new inhibitors of the enzymes involved in the biosynthesis of aromatic amino acids ... effort has been focused on the discovery of new inhibitors of the enzymes involved in the biosynthesis of aromatic amino acids ...

http://www.eurekaselect.com/134331/article

The aroA mutant strains fail to grow in tissue because they are unable to synthesize chorismic acid, from whichp-aminobenzoic ... acid, aromatic amino acids, and folate are produced. p-Aminobenzoic acid is required for folate biosynthesis, and exogenous ... The deduced amino acid sequence (350 amino acids) was 80% homologous to the phenylalanine-repressible phospho-2-dehydro-3- ... DNA bases (top line) and amino acids (one-letter code) (below) are listed and numbered to the right of the sequences. The ATG ...

https://iai.asm.org/content/66/5/1813

Chorismic Acid. 1. + +. 184. Interleukin-2. 1. + +. 185. Phenothiazines. 1. + +. 186. Bacterial Proton-Translocating ATPases. 1 ...

https://lookfordiagnosis.com/results.php?symptoms=Tuberculosis%2C+Multidrug-Resistant%3B%20Tuberculosis%2C%20Drug-Resistant&lang=1&parent=%2F&mode=F&therapy_ap=1

Dehydration and reduction of the latter give shikimic acid which is eventually converted to chorismic acid. Chorismic acid ... From both amino acids 4-hydroxycinnamic acid (p-coumaric acid) is generated. Upon esterification with coenzyme A 4- ... By means of the reference polyphenol gallic acid total polyphenolics are quantified as gallic acid equivalents (GAE) per kg or ... In the presence of sulfuric acid vanillin reacts with condensed flavan-3-ols (oligomers and polymers) to a red colored complex ...

https://nutritionj.biomedcentral.com/articles/10.1186/s12937-016-0218-1

CmlE and CmlD are required for chorismic acid synthesis, where chorismic acid is a precursor for both aromatic amino acid and ... Zuker M: Mfold web server for nucleic acid folding and hybridization prediction. Nucleic Acids Res. 2003, 31: 3406-3415. ... Nucleic Acids Res. 2010, 38 (Web Server issue): W695-W699.PubMed CentralView ArticlePubMedGoogle Scholar. ... Nucleic Acids Res. 2008, 36 (Web Server issue): W79-W84.PubMed CentralView ArticlePubMedGoogle Scholar. ...

https://bmcgenomics.biomedcentral.com/articles/10.1186/1471-2164-14-558

... and p-aminobenzoic acid and the purification of biologically derived acetaminophen. ... i. chorismic acid to p-aminobenzoic acid (PABA) (pathway step a);. *ii. p-aminobenzoic acid to p-aminophenol (pathway step b); ... The strains encode enzymes that convert the native yeast metabolite chorismic acid to p-aminobenzoic acid, p-aminobenzoic acid ... chorismic acid to p-aminobenzoic acid (PABA) (pathway step a); ii. p-aminobenzoic acid to p-aminophenol (pathway step b); and ...

https://patents.google.com/patent/US20170211104A1/en

Chorismic Acid. *Coenzyme A. Grant support. *AI42738/AI/NIAID NIH HHS/United States ...

https://www.ncbi.nlm.nih.gov/pubmed/9831524?dopt=Abstract

Intermediate in the biosynthesis of aromatic amino acids via the shikimate pathway. (sigmaaldrich.com)
[4] Biosynthesis can be impaired by disrupting the aro pathway which is responsible for the synthesis of chorismic acid from shikimate. (wikipedia.org)
Early studies in tobacco pointed to a role for the phenylpropanoid pathway, with benzoic acid as the immediate metabolic precursor to SA [ 9 ]. (portlandpress.com)
AtICS1:EC 5.4.4.2, also known as isochorismate hydroxymutase) as the enzyme encoded by the wild-type SID2 allele showed that, in this plant, SA is synthesised from chorismic acid, derived from the shikimic acid pathway, and that SA biosynthesis occurs in the plastid [ 5 , 10 - 12 ]. (portlandpress.com)
Among these, salicylic acid (SA) signaling is an important pathway because of its ability to trigger plant cell death. (frontiersin.org)
Radiolabeling studies with untreated leaves showed that SA was synthesized from phenylalanine and that both cinnamic and benzoic acid were intermediates in the biosynthesis pathway. (plantphysiol.org)
Several virulent strains have been attenuated by inactivation of genes in the aromatic amino acid biosynthesis pathway. (asm.org)
In the past few years a great deal of effort has been focused on the discovery of new inhibitors of the enzymes involved in the biosynthesis of aromatic amino acids, also known as the shikimic acid pathway, in which chorismic acid is synthesized. (eurekaselect.com)
The carbon flux through tricarboxylic acid cycle significantly reduced, while responses of the pentose phosphate pathway and the glycolysis to high SA production were rather weak, in the strain BSSA/pSA AroA /pDGSA AroD . (biomedcentral.com)
This pathway (unique to plants) leads to the formation of the aromatic amino acids phenylalanine and tyrosine and to the formation of many other phenyl-C3 compounds. (slideplayer.com)
3 GLUCOSE ORIGINS OF THE SHIKIMIC ACID PATHWAY PEP Acetyl-CoA pentose phosphate pathway glycolysis Erythrose-4-phosphate PEP Phosphoenol pyruvate The pentose phosphate pathway is one that converts glucose into sugars of different sizes (different numbers of C) by acyl interchanges. (slideplayer.com)
10 PHENYLALANINE AND TYROSINE COME FROM A COMMON SOURCE AND ARE NOT CONVERTED PREPHENIC ACID phenylpyruvic acid 4-hydroxyphenylpyruvic acid X tyrosine phenylalanine Although most plants could convert phenylalanine to tyrosine using hydroxylases, this conversion is a minor pathway. (slideplayer.com)
In particular, the present invention is directed to processes for producing shikimic acid that comprise contacting glyphosate and an organism that has the common aromatic biosynthetic pathway. (patentsencyclopedia.com)
The discovery of abyssomicin class of natural products has been the outcome of the search for secondary metabolites possessing inhibitory effect on p-aminobenzoic (pABA) acid biosynthesis, a biosynthetic pathway found in many microorganisms but not in humans. (ac.rs)

It is a precursor for: The aromatic amino acids phenylalanine, tryptophan, and tyrosine Indole, indole derivatives and tryptophan 2,3-Dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis The plant hormone salicylic acid Many alkaloids and other aromatic metabolites. (wikipedia.org)
Fenamic acid is a derivative of anthranilic acid, which in turn is a nitrogen isostere of salicylic acid, which is the active metabolite of aspirin. (wikipedia.org)
Methyl anthranilate and methyl salicylate are carboxyl methyl esters of anthranilic acid, an intermediate of Trp biosynthesis, and the plant hormone salicylic acid, respectively. (plantphysiol.org)
In all these species, methyl salicylate is synthesized by the action of S -adenosyl- l -methionine:salicylic acid carboxyl methyltransferase (SAMT). (plantphysiol.org)
Spraying potato ( Solanum tuberosum L.) leaves with arachidonic acid (AA) at 1500 μg mL −1 led to a rapid local synthesis of salicylic acid (SA) and accumulation of a SA conjugate, which was shown to be 2- O -β-glucopyranosylsalicylic acid. (plantphysiol.org)
After 1 h, the reaction was terminated using 0.1 mL 5 M HCl, the mixture was extracted and salicylic acid was estimated as described above. (pka-inhibitor.com)

Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. (wikipedia.org)
Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. (wikipedia.org)
The anion [C6H4(NH2)(CO2)]−, obtained by the deprotonation of anthranilic acid, is called anthranilate. (wikipedia.org)
Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L1 in that context, but it is now known to be non-essential in human nutrition. (wikipedia.org)
Solid anthranilic acid consists of both the amino-carboxylic acid and the zwitterionic ammonium carboxylate forms. (wikipedia.org)
Many routes to anthranilic acid have been described. (wikipedia.org)
In the era when indigo dye was obtained from plants, it was degraded to give anthranilic acid. (wikipedia.org)
Anthranilic acid was first obtained by base-induced degradation of indigo. (wikipedia.org)
Anthranilic acid is biosynthesized from chorismic acid. (wikipedia.org)
Industrially, anthranilic acid is an intermediate in the production of azo dyes and saccharin. (wikipedia.org)
Chlorination of anthranilic acid gives the 2,4-dichloro derivative, which can undergo reductive coupling to form a biaryl compound. (wikipedia.org)
Anthranilic Acid (Vitamin L)]". Florida State University. (wikipedia.org)
In vitro biochemical characterization after bacterial expression revealed three S -adenosyl- l -methionine-dependent methyltransferases with high specificity for anthranilic acid as a substrate. (plantphysiol.org)
Of these three proteins, Anthranilic Acid Methyltransferase1 (AAMT1) appears to be responsible for most of the S -adenosyl- l -methionine-dependent methyltransferase activity and methyl anthranilate formation observed in maize after herbivore damage. (plantphysiol.org)
Homology-based structural modeling combined with site-directed mutagenesis identified two amino acid residues, designated tyrosine-246 and glutamine-167 in AAMT1, which are responsible for the high specificity of AAMTs toward anthranilic acid. (plantphysiol.org)
In maize, this gene family has diversified especially toward benzenoid carboxyl methyltransferases that accept anthranilic acid and benzoic acid. (plantphysiol.org)
anthranilic acid See chorismic acid. (carlosbezerrajr.com.br)
Mechanism a in the top left structure leads to anthranilic acid and tryptophan, while mechanism b leads to p-aminobenzoic acid. (phrygane.tk)

In organisms capable of tryptophan synthesis, anthranilate is a precursor to the amino acid tryptophan via the attachment of phosphoribosyl pyrophosphate to the amine group. (wikipedia.org)
[5] Chorismic acid is the precursor of pyocyanin. (wikipedia.org)
Lumen, 2007) Tryptophan (trp) operon 'The trp operon of E. coli controls the biosynthesis of tryptophan in the cell from the initial precursor chorismic acid. (powtoon.com)
Requirement of p -aminobenzoic acid (PABA), a precursor of folic acid that is not synthesized by mammals, has been singled out as the likely reason for reduced virulence of these bacterial strains ( 25 ). (asm.org)

One such nutritional limitation is the availability of aromatic amino acids (AAAs) as animals lack the enzymes to synthesize tryptophan (Trp) and phenylalanine and only produce tyrosine from dietary phenylalanine. (frontiersin.org)
The route from chorismic acid to tryptophan is found in plants and micro-organisms only. (phrygane.tk)

Similar results were obtained when leaves were fed with the labeled putative intermediates cinnamic acid and benzoic acid. (plantphysiol.org)

The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. (wikipedia.org)
P. aeruginosa usually secreted four phenazines, pyocyanin (PYO), phenazine-1-carboxamide (PCN), 1-hydroxyphenazine (1-HP) and phenazine-1-carboxylic acid (PCA). (pubmedcentralcanada.ca)
These natural pigments comprise blue for pyocyanin (PYO), yellow for phenazine-1-carboxylic acid (PCA) and phenazine-1-carboxamide (PCN) and orange for 1-hydroxyphenazine (1-HP). (pubmedcentralcanada.ca)
Phenazine-1-carboxylic acid (Phenazine-1-carboxylate, PCA), which is produced from chorismic acid. (pubmedcentralcanada.ca)
We found significant differences in substrate-dependent phenazine production and resulting anodic current generation for the three strains, with the BES isolate KRP1 being overall the best current producer and showing the highest electrochemical activity with glucose as a substrate (19 μA cm −2 with ∼150 μg ml −1 phenazine carboxylic acid as a redox mediator). (asm.org)
Phenazines are synthesized from chorismic acid ( 19 , 20 ) via the intermediate phenazine-1-carboxylic acid (PCA), which is further converted into pyocyanin (PYO), 1-hydroxyphenazine (1-HP), and phenazine-carboxyamide (PCN) ( 21 ). (asm.org)
R Amino group H2N Cα carboxylic acid group COOH α- carbon H FIG. 1. (manualzz.com)

This cation can be used to generate benzyne, dimerized to give diphenic acid, or undergo diazonium coupling reactions such as in the synthesis of methyl red. (wikipedia.org)
Nieβner N, Mühlebach A, Lyerla JR (1993) Synthesis of isotopically labelled monomers and polymers of 4-hydroxybenzoic acid and 6-hydroxy-2-naphthoic acid. (springer.com)
When the amino acid is not there, the repressor moves away from the operator and RNA synthesis continues. (powtoon.com)
Translation 'is the process of translating the sequence of a messenger RNA (mRNA) molecule to a sequence of amino acids during protein synthesis. (powtoon.com)
Shikimic acid (SA) is a key chiral starting molecule for the synthesis of the neuramidase inhibitor GS4104 against viral influenza. (biomedcentral.com)
Shikimic acid (SA) is utilized in the synthesis of oseltamivir-phosphate, an anti-influenza drug. (biomedcentral.com)

The name chorismic acid derives from a classical Greek word χωρίζω meaning "to separate", because the compound plays a role as a branch-point in aromatic amino acid biosynthesis. (wikipedia.org)
Engineering of Aromatic Amino Acid Metabolism in Saccharomyces cerevisiae Zeynep Vuralhan Engineering of Aromatic Amino Acid Metabolism in Saccharomyces cerevisiae PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Technische Universiteit Delft, op gezag van de Rector Magnificus Prof. dr. ir. (manualzz.com)

The present invention generally relates to processes for producing and recovering cyclitolcarboxylic acids such as shikimic acid and quinic acid. (patentsencyclopedia.com)

Chorismate is transformed into para-aminobenzoic acid by the enzymes 4-amino-4-deoxychorismate synthase and 4-amino-4-deoxychorismate lyase. (wikipedia.org)
In these enzymes, the flavin plays either a direct role in acid/base reactions or as a nucleophile or electrophile. (mdpi.com)
I have published on such topics as pyridoxal phosphate (vitamin B6) enzymes, chorismic acid metabolizing enzymes and bio-sensors and bio-fuel cells. (roundtablegroup.com)
Abyssomicin C was the first natural product to act as an inhibitor of the enzymes involved in pABA and folic acid biosynthesis. (ac.rs)

Application of 2-aminoindan-2-phosphonic acid at 40 μ m , an inhibitor of phenylalanine ammonia-lyase, prior to treatment with AA inhibited the local accumulation of SA. (plantphysiol.org)

They can also be formed from phenylpyruvic acid as in the formation of tyrosine. (phrygane.tk)

Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. (wikipedia.org)

The nucleotide sequence of the A. hydrophila aroA gene encoded a protein of 440 amino acids which showed a high degree of homology to other bacterial AroA proteins. (asm.org)
107 1 GENERAL INTRODUCTION 1.0 Amino acids as building blocks for biomass constituents Amino acids are α-substituted carboxylic acids, the building blocks of proteins. (manualzz.com)
In addition to the amino acids synthesized by posttranslational modifications in proteins, there are some other amino acids such as ornithine and citrulline, which are the intermediates in the biosynthesis of arginine and the urea cycle (66). (manualzz.com)

a, model UPEC strain UTI89 produces three siderophores derived from chorismic acid precursors. (nih.gov)
Schmid HV, Zenk MH (1971) p -hydroxybenzoic acid and mevalonic acid as precursors of the plant naphthoquinone alkannin. (springer.com)

Chorismic acid is a metabolite generally used in the study of chorismate-prephenate rearrangement and to synthesize chorismate derivatives. (sigmaaldrich.com)

When transformed with a recombinant vector carrying the ubiC gene (encoding chorismate pyruvate-lyase, EC 4.1.3.27) the triple mutant (Phe − , Trp − , Tyr − ) Klebsiella pneumoniae 62-1 excretes 4-hydroxybenzoic acid instead of chorismic acid. (springer.com)
The recombinant strain can be used to produce in high yield specifically ring-labelled 4-hydroxybenzoic acid from isotopically labelled glucose. (springer.com)

The present disclosure relates compositions and methods for the biosynthetic production of medicinal supplements such as acetaminophen and intermediates including p-aminophenol, poly(p-aminophenol), and p-aminobenzoic acid (PABA). (google.com)

The genetic code describes the relationship between the sequence of base pairs in a gene and the corresponding amino acid sequence that it encodes. (powtoon.com)

Examples include the original Boots method which involves nitration of phenol with sulfuric acid and sodium nitrate giving a mixture of two isomers, from which the desired 4-nitrophenol is separated by steam distillation. (google.com)

The aroA mutant strains fail to grow in tissue because they are unable to synthesize chorismic acid, from which p -aminobenzoic acid, aromatic amino acids, and folate are produced. (asm.org)

Haslam E (1993) Shikimic acid-metabolism and metabolites. (springer.com)
Central carbon metabolism and shikimic acid pathways in E. coli PB12 strain lacking the PTS . (biomedcentral.com)

Mitochondrial electron carrier's ubiquinone and nicotinic acid are also susceptible to pyocyanin. (wikipedia.org)

Schmidt K, Leistner E (1995) Microbial production of (+)- trans -isochorismic acid. (springer.com)
At the end of the reaction, the BGB324 pH of each mixture was carefully adjusted to 2 using 6 M HCl and extracted twice with ethyl acetate (2 × 5 mL) to remove any isochorismic acid that had been formed. (pka-inhibitor.com)

Further elaboration of the cycloadduct produced the abyssomicin C. Related but different strategy employed the Lewis acid-templated intermolecular Diels-Alder reaction to assemble a highly substituted cyclohexane product (above scheme, path B). The cyclohexane ring formation via the cycloaddition reaction was followed by introduction of the tetronic moiety to form the spiro compound. (ac.rs)

Apart from 20 common amino acids, there are also amino acids that are modified after the protein is synthesized. (manualzz.com)

These galactolipid synthases are regulated by light, plant hormones, redox state, phosphatidic acid levels, and various stress conditions such as drought and nutrient limitation. (sykinhibitors.com)

Figure 8.5 Aromatic compounds from chorismic acid. (phrygane.tk)
Indole and skatole are used in various insects as pheromones Figure 8.5 Aromatic compounds from chorismic acid. (phrygane.tk)
Organometallics are also used in the production of simpler organic compounds, as in the industrial production of acetic acid using metal carbonyl catalysts , and in producing polymers such as polyethylene and poly propylene. (americanelements.com)
On the other hand, Dforms of amino acids are also natural compounds. (manualzz.com)

p -Aminobenzoic acid is required for folate biosynthesis, and exogenous folate cannot be taken up. (asm.org)

Industrially it is produced from phthalic anhydride, beginning with amination: C6H4(CO)2O + NH3 + NaOH → C6H4(C(O)NH2)CO2Na + H2O The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite: C6H4(C(O)NH2)CO2Na + HOCl → C6H4NH2CO2H + NaCl + CO2 A related method involves treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization. (wikipedia.org)

The present disclosure provides compositions and methods for the biosynthetic production of acetaminophen, p-aminophenol, and p-aminobenzoic acid and the purification of biologically derived acetaminophen. (google.com)

All 20 common amino acids have a carboxyl group and an amino group, which are attached to the same carbon atom. (manualzz.com)

D-amino acids are important building blocks in the production of pharmaceuticals, food additives, herbicides and other agrochemicals (66). (manualzz.com)

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The aroC gene of Aspergillus nidulans codes for a monofunctional, allosterically regulated chorismate mutase. (1/70)

Characterization of hydroxylaminobenzene mutase from pNBZ139 cloned from Pseudomonas pseudoalcaligenes JS45. A highly associated SDS-stable enzyme catalyzing an intramolecular transfer of hydroxy groups. (2/70)

Archaeal shikimate kinase, a new member of the GHMP-kinase family. (3/70)

Essential PchG-dependent reduction in pyochelin biosynthesis of Pseudomonas aeruginosa. (4/70)

The structures of anthranilate synthase of Serratia marcescens crystallized in the presence of (i) its substrates, chorismate and glutamine, and a product, glutamate, and (ii) its end-product inhibitor, L-tryptophan. (5/70)

Microbial origin of plant-type 2-keto-3-deoxy-D-arabino-heptulosonate 7-phosphate synthases, exemplified by the chorismate- and tryptophan-regulated enzyme from Xanthomonas campestris. (6/70)

The emerging periplasm-localized subclass of AroQ chorismate mutases, exemplified by those from Salmonella typhimurium and Pseudomonas aeruginosa. (7/70)

Clustering of isochorismate synthase genes menF and entC and channeling of isochorismate in Escherichia coli. (8/70)

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Electrodes

Pseudomonas aeruginosa

Electron Transport

Nanowires

Tuberculosis

Tuberculosis, Pulmonary

Tuberculosis, Multidrug-Resistant

Mycobacterium tuberculosis

Extensively Drug-Resistant Tuberculosis

Medical History Taking

Drug Resistance, Multiple, Bacterial

The aroC gene of Aspergillus nidulans codes for a monofunctional, allosterically regulated chorismate mutase. (1/70)

Characterization of hydroxylaminobenzene mutase from pNBZ139 cloned from Pseudomonas pseudoalcaligenes JS45. A highly associated SDS-stable enzyme catalyzing an intramolecular transfer of hydroxy groups. (2/70)

Archaeal shikimate kinase, a new member of the GHMP-kinase family. (3/70)

Essential PchG-dependent reduction in pyochelin biosynthesis of Pseudomonas aeruginosa. (4/70)

The structures of anthranilate synthase of Serratia marcescens crystallized in the presence of (i) its substrates, chorismate and glutamine, and a product, glutamate, and (ii) its end-product inhibitor, L-tryptophan. (5/70)

Microbial origin of plant-type 2-keto-3-deoxy-D-arabino-heptulosonate 7-phosphate synthases, exemplified by the chorismate- and tryptophan-regulated enzyme from Xanthomonas campestris. (6/70)

The emerging periplasm-localized subclass of AroQ chorismate mutases, exemplified by those from Salmonella typhimurium and Pseudomonas aeruginosa. (7/70)

Clustering of isochorismate synthase genes menF and entC and channeling of isochorismate in Escherichia coli. (8/70)

Pyocyanin - Wikipedia

Molecular Determinants for Rate Acceleration in the Claisen Rearrangement Reaction - edoc

RCSB PDB - 1K0E: THE CRYSTAL STRUCTURE OF AMINODEOXYCHORISMATE SYNTHASE FROM FORMATE GROWN CRYSTALS Methods Report...

The lipid-reactive oxygen species phenotype of breast cancer. Raman spectroscopy and mapping, PCA and PLSDA for invasive ductal...

UniProt: F2PQI4 TRIEC

Chorismate to PHB in Yeast?

Chorismate mutase - Wikipedia

trpE2 protein (Synechocystis sp. PCC6803) - STRING database

WikiGenes - NPL - N-acetylneuraminate pyruvate lyase...

A new salicylate synthase AmS is identified for siderophores biosynthesis in Amycolatopsis methanolica 239(T). | Sigma-Aldrich

AID 52148 - The compound was tested for inhibition of Bacillus subtilis chorismate mutase (BcCM) - PubChem

shikimate kinase(EC 2.7.1.71) - Creative Enzymes

Replacement of two invariant serine residues in chorismate synthase provides evidence that a proton relay system is essential...

trpB protein (Burkholderia cepacia) - STRING interaction network

RCSB PDB - 1COM: THE MONOFUNCTIONAL CHORISMATE MUTASE FROM BACILLUS SUBTILIS: STRUCTURE DETERMINATION OF CHORISMATE...

3-(2-Aminoethyl)indol-5-ol p-aminobenzoate dihydrochloride | C17H19Cl2N3O2 - PubChem

OSB Combiline | EGGER