646547

Tris(2-carboxyethyl)phosphine hydrochloride solution

0.5 M, pH 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)

• Synonym(s): TCEP
• Empirical Formula (Hill Notation): C₉H₁₅O₆P · HCl
• CAS Number: 51805-45-9
• Molecular Weight: 286.65
• MDL number: MFCD00145469
• UNSPSC Code: 12352128
• PubChem Substance ID: 24883469
• NACRES: NA.25

Properties

• concentration: 0.5 M
• refractive index: n20/D 1.367
• pH: 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)
• density: 1.041 g/mL at 25 °C
• SMILES string: Cl.OC(=O)CCP(CCC(O)=O)CCC(O)=O
• InChI: 1S/C9H15O6P.ClH/c10-7(11)1-4-16(5-2-8(12)13)6-3-9(14)15;/h1-6H2,(H,10,11)(H,12,13)(H,14,15);1H
• InChI key: PBVAJRFEEOIAGW-UHFFFAOYSA-N

Description

General description

It belongs to the trialkylphosphine class.

Tris (2-carboxyethyl) phosphine (TCEP) is very effective in cleaving disulfide bonds in aqueous solution. It dissolves in water and is odorless, unlike other trialkylphosphines (tributylphosphine). It is also less toxic than 2-mercaptoethanol. These advantages make it better than the other reducing agents.

Application

Tris (2-carboxyethyl) phosphine (TCEP) can be used in several downstream applications including SDS-PAGE, mass spectrometry, labeling with cysteine specific tags, and modification of cysteine containing compounds. It prevents oxidation of protein samples, which makes it a useful buffer component as it helps to preserve enzymatic activity. It has been used in the reduction and measurement of glutathione.

Tris (2-carboxyethyl) phosphine (TCEP) has also been used:

• to cleave cysteine residues in a synthetic peptide
• in reduction buffer for RNA Sequential Probing of Targets (SPOTs) imaging
• for the reduction of oligonucleotides
• as reducing agent during mitochondrial isolation

Biochem/physiol Actions

As a non-mercaptan reducing agent, it avoids the toxicity inherent in thiol-containing compounds. It is capable of disrupting the botulinum neurotoxin B heavy-chain/light-chain complex that is held together by a single disulfide bond, and that is responsible for endocytosis, and ultimately the toxicity, of the toxin. Since disulfide-coupled subunits are characteristic of many toxins (e.g., ricin, snake venom, and all BoNT serotypes), it may be useful as a rescue prophylactic in cases of toxin administration.

Tris(2-carboxyethyl)phosphine hydrochloride solution reduces the disulfide bonds and leaves other functional groups intact in proteins.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves