Tris(2-carboxyethyl)phosphine hydrochloride
[CAS# 51805-45-9]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Tris(2-carboxyethyl)phosphine hydrochloride
• Molecular Formula: C₉H₁₅O₆P.HCl
• Molecular Weight: 286.65
• CAS Registry Number: 51805-45-9
• EC Number: 629-759-1
• SMILES: C(CP(CCC(=O)O)CCC(=O)O)C(=O)O.Cl

Properties

• Solubility: Soluble (water)
• Melting point: 117 °C

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314-H318
• Safety Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1A	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 3261

Discovery and Applications

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP·HCl) is a widely used reducing agent in biochemical research and molecular biology. TCEP·HCl has become an important tool for reducing disulfide bonds in proteins and other biomolecules due to its stability and effectiveness.

TCEP·HCl was developed in the late 1980s as an alternative to traditional thiol-based reducing agents such as dithiothreitol (DTT) and β-mercaptoethanol. The search for a more stable and less odorous compound led to the synthesis of TCEP·HCl, which has better solubility and is easier to handle in aqueous solutions.

TCEP·HCl is a phosphine derivative with the chemical formula C9H15O6P·HCl. It is highly soluble in water and other polar solvents and, unlike thiol-based reducing agents, does not produce unpleasant odors or toxic byproducts. TCEP·HCl is stable over a wide pH range, making it suitable for a variety of biochemical applications.

TCEP·HCl reduces disulfide bonds by converting them to free thiols without forming disulfide intermediates. This mechanism is beneficial in maintaining the native structure of proteins and preventing oxidation during biochemical assays. Its ability to effectively break disulfide bonds while remaining stable in solution makes it a top choice for reducing applications.

TCEP·HCl is widely used to reduce disulfide bonds in proteins to aid in denaturation and preparation for electrophoresis, mass spectrometry, and structural analysis. In proteomics, it is used to reduce and alkylate proteins prior to digestion, improving peptide mapping and mass spectrometry protein identification.

TCEP·HCl helps reduce disulfide bonds in the active site of enzymes, preserving enzyme functionality and making it possible to study their catalytic properties. Some enzymes require reduction of disulfide bonds for activation, and TCEP·HCl provides a non-reactive and efficient method to achieve this without interfering with enzyme activity.

TCEP·HCl is used in the preparation of antibody-drug conjugates (ADCs) to reduce interchain disulfide bonds to allow attachment of cytotoxic agents or other probes to antibodies.

TCEP·HCl reduces oxidized nucleotides in DNA and RNA, which helps to study oxidative damage and its effects on genetic material.

TCEP·HCl has several advantages over traditional reducing agents: it is less toxic and less volatile, making it safer and more comfortable to use; it is stable under both acidic and alkaline conditions and is not easily oxidized; and unlike thiol-based reducing agents, it does not interfere with subsequent reactions such as thiol modification or labeling.

References

2024. Quantitative analysis of electroporation-mediated intracellular delivery via bioorthogonal luminescent reaction. Communications Chemistry, 7(1).
DOI: 10.1038/s42004-024-01266-4

2024. Highly sensitive detection of MMP-2 using an electrochemiluminescent biosensor enhanced by ladder-branch hybridization chain reaction. Microchimica Acta, 191(11).
DOI: 10.1007/s00604-024-06761-y

2024. A SERS and Fluorescence Dual-Signal Aptasensor for AFB1 Detection Based on DTNB Labeled AuNPs and CdTe Quantum Dots. Food Analytical Methods, 17(11).
DOI: 10.1007/s12161-024-02715-5