Introduction：Basic information about PHOSPHOENOLPYRUVIC ACID MONOPOTASSIUM SALT CAS 4265-07-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
PHOSPHOENOLPYRUVIC ACID MONOPOTASSIUM SALT Basic information
| Product Name: | PHOSPHOENOLPYRUVIC ACID MONOPOTASSIUM SALT |
| Synonyms: | 2H-1-Benzopyran-2-carboxylic acid, 6-chloro-3,4-dihydro-, (2S);2-(Phosphonooxy)-2-propenoic acid monopotassium sal;Phosphoenolpyruvic Acid Monopotassium Salt 〔PEP, Monopotassium Salt〕;2-(phosphonooxy)-2-propenoicacimonopotassiumsalt;Potassium 1-carboxyvinyl hydrogenphosphate;Phospho(enol)pyruvic acid MonopotassiuM salt 99%;PEP-K;PEP MONOPOTASSIUM SALT |
| CAS: | 4265-07-0 |
| MF: | C3H4KO6P |
| MW: | 206.13 |
| EINECS: | 224-247-0 |
| Product Categories: | Building Blocks;Chemical Synthesis;Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds;metabolite |
| Mol File: | 4265-07-0.mol |
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PHOSPHOENOLPYRUVIC ACID MONOPOTASSIUM SALT Chemical Properties
| Melting point | 175 °C (dec.)(lit.) |
| storage temp. | 2-8°C |
| solubility | Methanol (Slightly), Water (Slightly) |
| form | solid |
| color | White to off-white |
| Water Solubility | Soluble in water. Slightly soluble in methanol. |
| Sensitive | Hygroscopic |
| BRN | 4603446 |
| InChI | InChI=1S/C3H5O6P.K/c1-2(3(4)5)9-10(6,7)8;/h1H2,(H,4,5)(H2,6,7,8);/q;+1/p-1 |
| InChIKey | SOSDSEAIODNVPX-UHFFFAOYSA-M |
| SMILES | P([O-])(=O)(O)OC(=C)C(=O)O.[K+] |
| CAS DataBase Reference | 4265-07-0(CAS DataBase Reference) |
| EPA Substance Registry System | 2-Propenoic acid, 2-(phosphonooxy)-, monopotassium salt (4265-07-0) |
Safety Information
| Safety Statements | 24/25 |
| WGK Germany | 3 |
| F | 3-10 |
| TSCA | TSCA listed |
| HS Code | 29199000 |
| Storage Class | 13 - Non Combustible Solids |
PHOSPHOENOLPYRUVIC ACID MONOPOTASSIUM SALT Usage And Synthesis
| Description | Phosphoenolpyruvic acid plays a role in both glycolysis and gluconeogenesis. During glycolysis, it is formed by the action of enolase on 2-phosphoglycerate and is metabolized to pyruvate by pyruvate kinase. One molecule of ATP is formed during its metabolism in this pathway. During gluconeogenesis, it is formed from phosphoenolpyruvate carboxykinase-catalyzed oxaloacetate decarboxylation and GTP hydrolysis. In plants, it is metabolized to form aromatic amino acids and also serves as a substrate for phosphoenolpyruvate carboxylase-catalyzed carbon fixation. |
| Chemical Properties | white to light yellow fine crystalline powder |
| Uses | Substrate for many kinase reactions. |
| Uses | Phosphoenolpyruvic acid monopotassium salt is used in glycolysis and gluconeogeneis. It is used for regeneration of ATP from ADP in enzyme-catalyzed syntheses. It is metabolized by an enzyme namely pyruvate kinase to yield pyruvate. It acts as protection against cell injury induced by oxidative stress and against dysfunction in carbohydrate metabolism. |
| General Description | Phospho(enol)pyruvic acid (PEP) acts as an inhibitor of hexokinase, phosphoglucose isomerase, phosphofructokinase and aldolase. It is a bifunctional carbohydrate, which exhibits antioxidant property. PEP may be a potential organ preservation agent in clinical transplantation. |
| Biochem/physiol Actions | Phospho(enol)pyruvic acid (PEP) is involved in glycolysis and gluconeogeneis. In glycolysis, PEP is metabolized by Pyruvate Kinase to yield pyruvate. In plants, PEP is involved in the formation of aromatic amino acids as well as in the carbon fixation pathway. |
| Purification Methods | KPEP is purified via the monocyclohexylamine salt (see next entry). The salt (534mg) in H2O (10mL) is added to Dowex 50Wx4 H+ form (200-400 mesh, 2mL, H2O washed) and stirred gently for 30minutes and filtered. The resin is washed with H2O (6mL), and the combined solutions are adjusted to pH 7.4 with 3N KOH (~1.4mL) and the volume adjusted to 18.4mL with H2O to give a solution of 0.1M KPEP which can be lyophilised to a pure powder and is very good for enzyme work. It has been recrystallised from MeOH/Et2O. [Clark & Kirby Biochemical Preparations 11 103 1966, Wold & Ballou J Biol Chem 227 301 1957, Cherbuliez & Rabinowitz Helv Chim Acta 39 1461 1956, Beilstein 3 IV 977.] The triNa salt [5541-93-5] M 360.0, is purified as follows: the salt (1g) is dissolved in MeOH (40mL) and dry Et2O is added in excess. The white crystals are collected and dried over P2O5 at 20o. [Cramer & Voges Chem Ber 92 952 1959, Beilstein 3 IV 977.] |
| References | [1] MA. ENRIQUETA MU?OZ Elizabeth P. Pyruvate kinase: current status of regulatory and functional properties[J]. Comparative Biochemistry and Physiology B-Biochemistry & Molecular Biology, 2003, 135 2: Pages 197-218. DOI: 10.1016/s1096-4959(03)00081-2
[2] A MATTE. Structure and mechanism of phosphoenolpyruvate carboxykinase.[J]. The Journal of Biological Chemistry, 1997, 272 13: 8105-8108. DOI: 10.1074/jbc.272.13.8105
[3] HERRMANN K M. The Shikimate Pathway: Early Steps in the Biosynthesis of Aromatic Compounds.[J]. Plant Cell, 1995, 7 7: 907-919. DOI: 10.1105/tpc.7.7.907 |
PHOSPHOENOLPYRUVIC ACID MONOPOTASSIUM SALT Preparation Products And Raw materials
| Raw materials | 2-dihydroxyphosphinoyloxyacrylic acid |
| Preparation Products | CHORISMIC ACID |
