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68957

Sigma-Aldrich

Tris(2-carboxyethyl)phosphine hydrochloride

BioUltra, suitable for electrophoresis, SDS-PAGE tested

Synonym(s):

TCEP.HCL, TCEP

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About This Item

Empirical Formula (Hill Notation):
C9H15O6P · HCl
CAS Number:
51805-45-9
Molecular Weight:
286.65
Beilstein:
3724376
MDL number:
MFCD00145469
UNSPSC Code:
12352128
PubChem Substance ID:
329761275
NACRES:
NA.32

product line

BioUltra

Assay

97.5-102.5%

form

powder

technique(s)

electrophoresis: suitable

solubility

H2O: soluble

suitability

SDS-PAGE tested

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

Tris(2-carboxyethyl) phosphine hydrochloride (TCEP.HCL ) is a useful reducing agent for Sulphur and nitrogen-containing compounds. TCEP.HCL and the resultant oxide are water-soluble. TCEP.HCL has electron-rich phosphorus and oxygen atoms to combine with various metals, including Rh, Ir, and Pd. It rapidly complexes with Rh and Ir in dioxane at ambient temperature. It reduces disulfide linkages in a range of peptides and proteins in biological disulfide.

Application

TCEP.HCL has been used in various bioconjugation applications, both in vitro and in vivo, to tag proteins and live organisms with great effectiveness under mild physiological circumstances. TCEP.HCL is suitable for varied biological and synthetic applications. At an acidic pH, TCEP.HCL can be used to convert organic disulfides to thiols in water irreversibly.
Water soluble reagent, used for selective reduction of disulfides. More stable than DTT and useful in mass spectrometry applications.

Features and Benefits

The product has the following benefits:

  • TCEP.HCL lowers reactive oxygen species levels.
  • It increases glutathione levels and mitochondrial content.
  • It has anti-cancer effects.

Analysis Note

agarose gel electrophorese corresponds to requirements

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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W H Fischer et al.
Rapid communications in mass spectrometry : RCM, 7(3), 225-228 (1993-03-01)
The suitability of the hydrochloride salt of tris(2-carboxyethyl)phosphine (TCEP) for in situ reduction with matrix-assisted laser desorption/ionization (MALDI) and liquid secondary ionization (LSI) mass spectrometry is evaluated. TCEP can be used to irreversibly reduce organic disulfides to thiols in water
Christopher R Schlieve et al.
Experimental eye research, 83(5), 1252-1259 (2006-08-29)
Retinal ganglion cells (RGCs) undergo apoptosis after axonal injury, in part regulated by an intracellular superoxide anion burst, for which the target(s) are unknown. Shifting the RGC redox state towards reduction and preventing sulfhydryl oxidation is neuroprotective in vitro and
Siming Chen et al.
Chemical communications (Cambridge, England), 49(12), 1226-1228 (2013-01-05)
A widely used reducing agent tris-(2-carboxyethyl) phosphine significantly promotes the reaction of cisplatin with Sp1 zinc finger protein. This discovery clarifies the reactivity of cisplatin towards Sp1 zinc finger protein and implies that the reactions of platinum drugs could be
Yiren Zeng et al.
Theriogenology, 162, 32-41 (2021-01-15)
Oocyte in vitro maturation (IVM) is a crucial process that determines subsequent in vitro embryo production. The present study investigated the effects of the antioxidant tris (2-carboxyethyl) phosphine hydrochloride (TCEP-HCL) on the in vitro maturation of porcine oocytes and in vitro developmental competence of
Fang-Fang Cheng et al.
The Analyst, 139(16), 3860-3865 (2014-07-01)
The expression of microRNAs (miRNAs) is related to some cancer diseases. Recently, miRNAs have emerged as new candidate diagnostic and prognostic biomarkers for detecting a wide variety of cancers. Due to low levels, short sequences and high sequence homology among
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