C4706
Tris(2-carboxyethyl)phosphine hydrochloride
powder
description
Protect from moisture
Quality Level
form
powder
reaction suitability
reagent type: reductant
color
white
solubility
H2O: 50 mg/mL
storage temp.
2-8°C
SMILES string
Cl[H].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
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General description
Application
- As a reducing agent for the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides. It can also be used in azide-alkyne cycloaddition reaction in the presence of a copper catalyst.
- To reduce disulfide bonds in various proteins.
- As a reagent for the selective reduction of disulfides in water.
- To remove ruthenium-derived metathesis catalysts via aqueous washing of a crude reaction mixture when it is basified.
- As a reducing agent for the reduction of various alkyl disulfides such as trans-4,5-dihydroxy-1,2-dithiane.
Caution
related product
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Corr. 1B
Storage Class Code
8A - Combustible, corrosive hazardous materials
WGK
WGK 1
Personal Protective Equipment
Certificates of Analysis (COA)
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What is the primary function of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride?
Tris (2-carboxyethyl) phosphine hydrochloride (TCEP, #C4706) is capable of selectively cleaving disulfide bonds.
What is Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride, soluble in?
TCEP is soluble in water at 50 mg/ml and is also stable under both acidic and basic pH conditions. For work in protein analysis and mass spectrometry, we also offer an already prepared version of TCEP in a buffered aqueous solution. Product# 646547 is 0.5M solution of TCEP in water, where the pH has been adjusted to 7 with ammonium hydroxide.
What is the benefit of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP), over traditional disulfide reduction agents, like DTT (dithiothreitol) and BME (beta-mercaptoethanol)?
TCEP is a very effective disulfide reducing agent that is less toxic than beta-mercaptoethanol and more stable to solution oxidation and pH changes than dithiothreitol.
Where can I find protocols that cite the use of Product C4706, Tris(2-carboxyethyl)phosphine hydrochloride (TCEP)?
1. Burns, J. A., et al. J. Org. Chem. 56, 1648, (1991)2. Maynard, H. D.; Grubbs, R. J. Tet. Lett. 40, 4137, (1999)3. Grubbs, R. H. Org. React. 22, 123, (2004)4. Burns, J.A. J. Org. Chem. 56, 2648, (1991)5. Kirley, T.L., Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analyses. Anal. Biochem. 180, 231-236, (1989)6. Fischer W.H, et al., In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine. Rapid Commun. Mass Spectrom. 7, 225-228, (1993)7. Getz, E.B., et al., A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry. Anal. Biochem. 273, 73-80, (1999) 8. Beil. 4,IV,3441
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Protocols
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