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Merck

646547

Supelco

Tris(2-carboxyethyl)phosphine hydrochloride solution

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

Sinónimos:

TCEP

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About This Item

Fórmula empírica (notación de Hill):
C9H15O6P · HCl
Número de CAS:
Peso molecular:
286.65
Número MDL:
Código UNSPSC:
12352128
ID de la sustancia en PubChem:
NACRES:
NA.25

Nivel de calidad

concentración

0.5 M

índice de refracción

n20/D 1.367

pH

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

densidad

1.041 g/mL at 25 °C

cadena SMILES

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

Clave InChI

PBVAJRFEEOIAGW-UHFFFAOYSA-N

Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Para utilizar con

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Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

Eye Dam. 1 - Skin Corr. 1B

Código de clase de almacenamiento

8A - Combustible corrosive hazardous materials

Clase de riesgo para el agua (WGK)

WGK 1

Equipo de protección personal

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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M C Gilbert Lee et al.
Journal of visualized experiments : JoVE, (87)(87), doi:10-doi:10 (2014-05-20)
Cell surface proteins, including extracellular matrix proteins, participate in all major cellular processes and functions, such as growth, differentiation, and proliferation. A comprehensive characterization of these proteins provides rich information for biomarker discovery, cell-type identification, and drug-target selection, as well
Defined DNA/nanoparticle conjugates
Ackerson CJ, et al.
Proceedings of the National Academy of Sciences of the USA, 102(38), 13383-13385 (2005)
Quantitative analysis of tris (2-carboxyethyl) phosphine by anion-exchange chromatography and evaporative light-scattering detection
Tan Z, et al.
Journal of Pharmaceutical and Biomedical Analysis, 59, 167-172 (2012)
Differential labeling of free and disulfide-bound thiol functions in proteins
Seiwert B, et al.
Journal of the American Society For Mass Spectrometry, 19(1), 1-7 (2008)
Highly multiplexed quantitative mass spectrometry analysis of ubiquitylomes
Rose CM, et al.
Cell Systems, 3(4), 395-403 (2016)

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In this study, we developed a rapid trypsin digest kit that, at elevated temperatures, yielded reliable, reproducible results in less than 2 hours on a wide variety of substrates for mass spectrometry.

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