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| Names | |
|---|---|
| IUPAC name 2,2',2"-Phosphanetriyltripropanoic acid | |
| Other names
TCEP Tris(2-carboxyethyl)phosphine | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| PubChem CID | |
| CompTox Dashboard (EPA) | |
SMILES
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| Properties | |
| Chemical formula | C9H15O6P |
| Molar mass | 250.187 g·mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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TCEP (tris(2-carboxyethyl)phosphine) is a reducing agent frequently used in biochemistry and molecular biology applications. It is often prepared and used as a hydrochloride salt (TCEP-HCl) with a molecular weight of 286.65 gram/mol. It is soluble in water and available as a stabilized solution at neutral pH and immobilized onto an agarose support to facilitate removal of the reducing agent.
Applications
TCEP is often used as a reducing agent to break disulfide bonds within and between proteins as a preparatory step for gel electrophoresis.
Compared to the other two most common agents used for this purpose (dithiothreitol and β-mercaptoethanol), TCEP has the advantages of being odorless, a more powerful reducing agent, an irreversible reducing agent, more hydrophilic, and more resistant to oxidation in air. It also does not reduce metals used in immobilized metal affinity chromatography.
TCEP is particularly useful when labeling cysteine residues with maleimides. TCEP can keep the cysteines from forming di-sulfide bonds and unlike dithiothreitol and β-mercaptoethanol, it will not react as readily with the maleimide. However, TCEP has been reported to react with maleimide under certain conditions.
References
- Ruegg, U.T and Rudinger, J. (1977). "Reductive cleavage of cystine disulfides with tributylphosphine". Methods Enzymol. 47: 111–126. doi:10.1016/0076-6879(77)47012-5. PMID 927167.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ TCEP technical information, from Interchim
- Shafer, D. E.; Inman, J. K.; Lees, A. (2002). "Reaction of Tris(2-carboxyethyl)phosphine (TCEP) with Maleimide and α-Haloacyl Groups: Anomalous Elution of TCEP by Gel Filtration". Anal. Biochem. 282 (1): 161–164. doi:10.1006/abio.2000.4609. PMID 10860517.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - Tyagarajan K, Pretzer E, Wiktorowicz JE (2003). "Thiol-reactive dyes for fluorescence labeling of proteomic samples". Electrophoresis. 24 (14): 2348–2358. doi:10.1002/elps.200305478. PMID 12874870.
{{cite journal}}: CS1 maint: multiple names: authors list (link)