TCEP

TCEP
Names


IUPAC name 3,3′,3′′-Phosphanetriyltripropanoic acid
Other names TCEP Tris(2-carboxyethyl)phosphine
Identifiers
CAS Number	51805-45-9^Y
3D model (Jmol)	Interactive image
ChemSpider	106653^N
ECHA InfoCard	100.157.950
PubChem CID	119411
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)^N Key: PZBFGYYEXUXCOF-UHFFFAOYSA-N^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	250.19 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

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.

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. 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.

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