Tris(2-carboxyethyl)phosphine hydrochloride solution

Name: Tris(2-carboxyethyl)phosphine hydrochloride solution
Brand: SIGMA

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

Synonym(s):

TCEP

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₅O₆P · HCl

CAS Number:

51805-45-9

Molecular Weight:

286.65

NACRES:

NA.25

PubChem Substance ID:

24883469

UNSPSC Code:

12352128

MDL number:

MFCD00145469

Product Name

Tris(2-carboxyethyl)phosphine hydrochloride solution, 0.5 M, pH 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)

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

SMILES string

Cl.OC(=O)CCP(CCC(O)=O)CCC(O)=O

InChI key

PBVAJRFEEOIAGW-UHFFFAOYSA-N

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

Quality Level

200

Related Categories

Analytical Reagents

Chromatography & Spectroscopy Reagents

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.

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.

pictograms

GHS05

signalword

Danger

hcodes

H314

pcodes

P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363 - P405

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 1

ppe

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

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Defined DNA/nanoparticle conjugates

Ackerson CJ, et al.

Proceedings of the National Academy of Sciences of the USA, 102(38), 13383-13385 (2005)

TCEP treatment reduces proteolytic activity of BoNT/B in human neuronal SHSY-5Y cells.

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

Glycopeptide capture for cell surface proteomics.

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

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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