Tris(2-carboxyethyl)phosphine (TCEP) is a well - known and highly useful reducing agent in the field of chemistry. As a supplier of TCEP, I am well - versed in its chemical properties, and I'm eager to share this knowledge with you.
Chemical Structure and Basic Information
TCEP has the molecular formula C₉H₁₅O₆P. Its chemical structure consists of a central phosphorus atom bonded to three 2 - carboxyethyl groups. The unique arrangement of atoms in its structure gives rise to several important chemical properties.
Reducing Ability
One of the most prominent chemical properties of TCEP is its strong reducing ability. TCEP can reduce disulfide bonds in proteins and other biomolecules. In comparison to other common reducing agents like dithiothreitol (DTT), TCEP has several advantages. It is more stable in aqueous solutions, especially at different pH values. While DTT can be easily oxidized in air and its reducing power may decrease over time, TCEP remains relatively stable.
The reduction reaction of disulfide bonds by TCEP occurs through a nucleophilic attack of the phosphorus atom on the sulfur - sulfur bond. The overall reaction can be represented as follows:
R - S - S - R' + TCEP → R - SH+ R' - SH+ Oxidized TCEP
This reaction is crucial in many biochemical and molecular biology applications. For example, in protein purification and analysis, disulfide bonds can cause proteins to form aggregates or adopt incorrect conformations. By using TCEP to break these disulfide bonds, proteins can be maintained in their monomeric and native - like states, which is essential for accurate structural and functional studies.
pH Stability
TCEP is stable over a wide pH range, typically from pH 1 to 10. This wide pH stability makes it suitable for a variety of applications in different chemical and biological systems. At acidic pH values, TCEP remains protonated and retains its reducing activity. In basic solutions, although there may be some minor changes in its reactivity, it still functions effectively as a reducing agent.
This pH stability is in contrast to some other reducing agents that may lose their activity or degrade rapidly outside a narrow pH range. For instance, some thiol - based reducing agents are highly sensitive to pH and can be easily oxidized or deprotonated at certain pH values, leading to a loss of their reducing power.
Solubility
TCEP is highly soluble in water, which is a significant advantage for its use in aqueous - based biological and chemical systems. Its good water solubility allows for easy preparation of solutions at various concentrations. In addition to water, TCEP is also soluble in some polar organic solvents such as dimethyl sulfoxide (DMSO) and ethanol.
This solubility property enables it to be used in a wide range of experimental setups. For example, in cell - based assays, TCEP can be easily incorporated into cell culture media due to its water solubility. In organic synthesis, its solubility in polar organic solvents allows it to participate in reactions that require non - aqueous environments.
Reactivity with Other Chemicals
TCEP can react with a variety of other chemicals in addition to disulfide bonds. It can react with certain metal ions, forming complexes. This property can be both an advantage and a disadvantage depending on the application. In some cases, the complexation with metal ions can be used for metal ion removal or detection. However, in other situations, it may interfere with reactions that involve metal - catalyzed processes.
TCEP can also react with some oxidizing agents. When exposed to strong oxidants such as hydrogen peroxide or hypochlorite, TCEP is oxidized to its corresponding phosphine oxide. This oxidation reaction can be used as a way to control the reducing activity of TCEP in a system.
Comparison with Other Flame - Retardant Phosphates
In the context of flame - retardant phosphates, TCEP has different chemical properties compared to other well - known compounds such as Isopropylate Triphenyl Phosphate 95, Tritolyl Phosphate, and Tributyl Phosphate.
Isopropylate Triphenyl Phosphate 95 is mainly used as a flame retardant and plasticizer. It has a relatively high thermal stability and can effectively reduce the flammability of polymers. Tritolyl Phosphate is also a widely used flame retardant, which has good compatibility with many polymers and can improve the mechanical properties of the materials to some extent. Tributyl Phosphate is often used as a solvent and extractant in addition to its flame - retardant properties.
In contrast, TCEP is not primarily used as a flame retardant. Its main function is as a reducing agent in chemical and biological systems. However, the phosphorus - containing structure of TCEP gives it some potential in flame - retardant research, although this is not its mainstream application at present.
Applications Based on Chemical Properties
The chemical properties of TCEP have led to its extensive use in various fields. In the pharmaceutical industry, TCEP is used in the synthesis and purification of peptides and proteins. It helps to maintain the correct disulfide bond formation in peptides, which is crucial for their biological activity.
In the field of materials science, TCEP can be used in the modification of polymers. By reducing disulfide bonds in polymer chains, the physical and chemical properties of the polymers can be altered. For example, the flexibility and solubility of polymers can be improved.
Conclusion
In conclusion, TCEP is a versatile chemical with unique and valuable chemical properties. Its strong reducing ability, wide pH stability, good solubility, and specific reactivity make it an indispensable reagent in many chemical and biological applications.
If you are interested in purchasing TCEP for your research or industrial needs, we are here to provide you with high - quality products. We can offer different grades and quantities of TCEP to meet your specific requirements. Please feel free to contact us for more information and to start a procurement negotiation.
References
- Hermanson, G. T. (2013). Bioconjugate Techniques. Academic Press.
- Voet, D., Voet, J. G., & Pratt, C. W. (2016). Fundamentals of Biochemistry: Life at the Molecular Level. Wiley.
