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Tris(2-carboxyethyl)phosphine hydrochloride solution

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

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

Quality Level

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

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.

related product

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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


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Xuerong Shi et al.
Journal of cellular biochemistry, 107(5), 1021-1030 (2009-06-06)
The light chain (LC) of botulinum neurotoxin B (BoNT/B) is unable to enter target neuronal cells by itself. It is brought into the cell in association with the BoNT/B heavy chain (HC) through endocytosis. The BoNT HC-LC subunits are held
Defined DNA/nanoparticle conjugates
Ackerson CJ, et al.
Proceedings of the National Academy of Sciences of the USA, 102(38), 13383-13385 (2005)
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
E B Getz et al.
Analytical biochemistry, 273(1), 73-80 (1999-08-24)
The newly introduced sulfhydryl reductant tris(2-carboxyethyl)phosphine (TCEP) is a potentially attractive alternative to commonly used dithiothreitol (DTT). We compare properties of DTT and TCEP important in protein biochemistry, using the motor enzyme myosin as an example protein. The reductants equally
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)

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