TCEP

TCEP
Names
	IUPAC name 3,3′,3′′-Phosphanetriyltripropanoic acid
	Other names TCEP; Tris(2-carboxyethyl)phosphine
Identifiers
CAS Number	51805-45-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	106653 ;
PubChem CID	119411;
CompTox Dashboard (EPA)	DTXSID90208290 ;
	InChI InChI=1S/C9H15O6P/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) Key: PZBFGYYEXUXCOF-UHFFFAOYSA-N ; InChI=1/C9H15O6P/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) Key: PZBFGYYEXUXCOF-UHFFFAOYAQ;
	SMILES OC(CCP(CCC(O)=O)CCC(O)=O)=O;
Properties
Chemical formula	C9H15O6P
Molar mass	250.187 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

TCEP (tris(2-carboxyethyl)phosphine) is a reducing agent frequently used in biochemistry and molecular biology applications.^[1] 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 (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.^[2] 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.^[2] However, TCEP has been reported to react with maleimide under certain conditions.^[3]^[4]

TCEP is also used in the tissue homogenization process for RNA isolation.^[5]

References

^ Ruegg, U.T; 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. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
^ ^a ^b 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.
^ Rhee, S. S.; Burke, D. H. (2004). "Tris(2-carboxyethyl)phosphine stabilization of RNA: comparison with dithiothreitol for use with nucleic acid and thiophosphoryl chemistry". Anal. Biochem. 325 (1): 137–143. doi:10.1016/j.ab.2003.10.019. PMID 14715294.

[1] Ruegg, U.T; 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. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)

[FT-242214-2] TCEP technical information, from Interchim

[3] 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.

[4] 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.

[5] Rhee, S. S.; Burke, D. H. (2004). "Tris(2-carboxyethyl)phosphine stabilization of RNA: comparison with dithiothreitol for use with nucleic acid and thiophosphoryl chemistry". Anal. Biochem. 325 (1): 137–143. doi:10.1016/j.ab.2003.10.019. PMID 14715294.

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