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About This Item
Empirical Formula (Hill Notation):
C9H15O6P · HCl
CAS Number:
Molecular Weight:
286.65
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352128
MDL number:
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
Related Categories
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.
signalword
Danger
hcodes
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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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)
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
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)
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
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