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|Molar mass||250.19 g mol−1|
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.
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 (in the sense that TCEP does not regenerate--the end product of TCEP-mediated disulfide cleavage is in fact two free thiols/cysteines), 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.
TCEP is also used in the tissue homogenization process for RNA isolation.
- Ruegg, U.T and Rudinger, J. (1977). "Reductive cleavage of cystine disulfides with tributylphosphine". Methods Enzymol. Methods in Enzymology 47: 111–116. doi:10.1016/0076-6879(77)47012-5. ISBN 978-0-12-181947-7. PMID 927167.
- 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.
- 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.