Phospho(enol)pyruvic acid monopotassium salt
[CAS# 4265-07-0]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Phospho(enol)pyruvic acid monopotassium salt
• Synonyms: 2-(Phosphonooxy)-2-propenoic acid monopotassium salt
• Molecular Formula: C₃H₄KO₆P
• Molecular Weight: 206.13
• CAS Registry Number: 4265-07-0
• EC Number: 224-247-0
• SMILES: C=C(C(=O)O)OP(=O)(O)[O-].[K+]

Properties

• Melting point: 170 $degree (decomp.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Phospho(enol)pyruvate monopotassium salt, commonly abbreviated as PEP, is an important biochemical compound with the molecular formula C3H4KO6P. The compound is the monopotassium salt form of phosphoenolpyruvate, a key intermediate in various metabolic pathways. PEP plays a vital role in both glycolysis and gluconeogenesis, making it fundamental to cellular energy production and metabolic regulation.

The discovery of PEP dates back to the early 20th century research into cellular metabolism. Researchers discovered that PEP is a key molecule in the conversion of glucose to pyruvate in the glycolysis pathway, a process essential for the production of ATP, the primary energy currency of the cell. The high-energy phosphate bond of PEP is particularly important because it helps drive the synthesis of ATP from ADP, a key step in cellular respiration.

One of the main applications of PEP is in biochemical research and clinical diagnostics. In research, PEP is widely used to study enzyme kinetics and metabolic processes. Its role in glycolysis makes it a valuable substrate for studying enzyme activities, such as pyruvate kinase, which catalyzes the transfer of a phosphate group from PEP to ADP to form ATP and pyruvate. Understanding these enzyme mechanisms is essential for elucidating cellular energy metabolism and developing treatments for metabolic disorders.

In clinical diagnostics, PEP is used in assays that measure the activity of enzymes involved in glucose metabolism. For example, it is used to diagnose pyruvate kinase deficiency, a genetic disorder that causes hemolytic anemia. By assessing the conversion of PEP to pyruvate, clinicians can diagnose and monitor this disease, providing important information for patient management.

PEP also has important applications in biotechnology and industrial processes. It is used to produce biofuels and bioplastics through microbial fermentation. In these processes, genetically engineered microorganisms are used to convert PEP into valuable chemicals and materials. For example, PEP can be used to synthesize ethanol or lactic acid, which are key intermediates in the production of bio-based products. This application highlights the importance of PEP in sustainable and environmentally friendly technologies.

In agriculture, PEP plays a role in improving crop productivity. Some biofertilizers contain PEP or its derivatives to stimulate plant growth and improve nutrient absorption. By affecting the metabolic pathways of plants, these biofertilizers can enhance photosynthesis and increase crop yields, thereby promoting sustainable agricultural practices.

In addition, the therapeutic potential of PEP is being explored. Recent studies have shown that PEP and its derivatives can be used to modulate metabolic pathways in cancer cells. Cancer cells have altered metabolism, and targeting key intermediates such as PEP could provide new avenues for cancer treatment. By disrupting energy production and biosynthetic processes in cancer cells, researchers aim to develop therapies that selectively target tumor growth while sparing normal cells.

Standard laboratory precautions are required for handling and storing PEP. The compound should be stored in a cool, dry place away from light and moisture. Appropriate safety precautions, including the use of gloves, goggles, and lab coats, are essential to prevent exposure and ensure safe handling. In addition, proper disposal methods should be followed to minimize environmental impact.

References

2020. PEP-K: A New Reagent for the O-Phosphorylation of Alcohols. Synfacts, 16(4).
DOI: 10.1055/s-0040-1707569

2021. A Single-Step Asymmetric Phosphodiester Synthesis from Alcohols with Phosphoenolpyruvate Phosphodiester. Synlett, 32(13).
DOI: 10.1055/a-1509-9275

2023. Citrate synthase from Cyanidioschyzon merolae exhibits high oxaloacetate and acetyl-CoA catalytic efficiency. Plant Molecular Biology, 111(4-5).
DOI: 10.1007/s11103-023-01335-7