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Tris(2-carboxyethyl)phosphine Hydrochloride CAS 51805-45-9 TCEP

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: TCEP Supplement

Basic Info of TCEP

What is TCEP?

TCEPhydrochloride (Tris(2-carboxyethyl)phosphinehydrochloride) is a non-thiol lowering agent that is extra stable than various other chemical decreasing agents and generates a much faster S-S reduction response. TCEPhydrochloride is a trialkylphosphine that uniquely decreases protein break down without modifying its residential properties or engaging with thiol guiding representatives in the reaction mixture. TCEPhydrochloride is also a commonly utilized lowering representative in DNA/AuNP chemistry.

TCEP hydrochloride, namely tris(2-carbonylethyl)phosphorus hydrochloride, has the most effective impact amongst trivalent phosphorus by-products. It is a colorless, odorless, weakly lowering material soluble in water, and its solubility in water can get to 310mg/mL. It has high security in air as well as aqueous option, and also is much less influenced by temperature level as well as concentration. TCEP is an extremely appropriate disulfide bond reducing reagent (decrease principle is shown in Figure 1). A wide pH range includes usage under acidic problems (pH 3), which efficiently minimizes the hydrolysis of amide bonds. TCEP has mild sensitivity, simple solubility, reduced toxicity, and also much easier procedure, as well as has good security in acidic as well as alkaline solutions. And its decreasing ability is stronger than DTT, more stable than DTT, its result can be kept for 2 to 3 weeks, it is recognized as a great alternative to DTT (dithiothreitol).

Tris(2-carboxyethyl)phosphine hydrochloride (TCEP hydrochloride) is an unique lowering and deprotecting agent for thiolated DNA. Thiolated DNA terminal sulfur atoms have a tendency to develop dimers in solution, particularly in the existence of oxygen. This dimerization greatly reduces the performance of some combining reaction experiments (such as DNA immobilization in biosensors); while tris(2-carboxyethyl)phosphine hydrochloride (TCEP hydrochloride) is contributed to the DNA service ), which can be eliminated after a period of response to reduce DNA dimerization. Tris (2-carboxyethyl) phosphine hydrochloride (TCEP hydrochloride) is also usually made use of for the decrease of disulfide bonds in proteins, which can be utilized to prevent intramolecular or intramolecular protein formation in between cysteines in healthy proteins. Intermolecular disulfide bonds. Tris(2-carboxyethyl)phosphine hydrochloride (TCEP hydrochloride) is much more steady than the standard reducing and deprotecting agents mercaptoethanol or dithiothreitol (DTT) for thiolated DNA, Difficult to be oxidized by air, with no annoying odor.

TCEP Uses

  1. TCEP is generally made use of as a minimizing representative to ruin disulfide bonds within and also between healthy proteins as a prep work action for gel electrophoresis.
  2. With the other 2 most frequently utilized reagents for this objective (dithiothreitol and also β- Compared to mercaptoethanol), TCEP has the advantages of unappetizing, extra powerful reductant and irreparable reductant (that is, TCEP will not regenerate – the end product of disulfide bond bosom mediated by TCEP is really two free mercaptans/ cysteine), which is more hydrophilic and immune to oxidation in the air. It likewise does not decrease the amount of steel used for paralyzed metal affinity chromatography.
  3. TCEP is particularly valuable when cysteine residues are labeled with maleimide. TCEP can protect against cysteine from creating disulfide bonds, and integrate with dithiothreitol and also β- Unlike mercaptoethanol, it does not react with maleimide. Nevertheless, TCEP has actually been reported to respond with maleimide under specific problems.
  4. For UV-Vis applications, TCEP works when it is essential to prevent the 250 to 285 nm disturbance absorbance that may accompany dithiothreitol. With the event of different redox responses and the passage of time, dithiothreitol will slowly take in increasingly more light in the range.
  5. Tris(2-carbonylethyl)phosphorus hydrochloride is an organophosphorus substance that can be made use of as a water-soluble reagent for the discerning decrease of disulfides; extra stable than DTT in mass spectrometry applications; can also be made use of in water Careful reduction of disulfides. After alkalization, the water-soluble ligand can be merely removed by aqueous cleaning of the unrefined item of the ruthenium-based metathesis driver.

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Application of TCEP

Preparation of TCEP

  • Preparation of compound trimethyl 3,3′,3″-phosphine triyl tripropionate
    Under the condition of mechanical stirring, 80% tetrahydroxymethylphosphorus chloride aqueous solution (71.2g, 0.30mol) and ethanol (75ml) were added to a 250ml reaction flask, cooled with ice water and protected by nitrogen, and then added with hydroxide Potassium (16.8g, 0.30mol) was dissolved in a solution of 23ml of ice water, and the temperature rose slightly; then ethyl acrylate (90g, 0.9mol) was added dropwise, and the temperature was controlled at 35-40°C, a large amount of solid was formed, and the temperature was kept stirring after dropping. 4 hours.
    Pour 300 ml of ice water into the reaction solution, filter with suction after stirring, wash the filter cake with ice water, and dry with suction to obtain 88 g of white solid (that is, compound trimethyl 3,3′,3″-phosphinetriyltripropylidene) acid ester), the yield was 86.6%, which was used for the next reaction. The nuclear magnetic data of the obtained product were as follows: 1HNMR (CDCl3, 400MHz): δ=1.27(t, 9H), 1.75(t, 6H), 2.45(dt, 6H), 4.15(q, 6H).
  • Preparation of compound tris(2-carboxyethyl)phosphine hydrochloride (TCEP hydrochloride)
    Under the condition of mechanical stirring, the trimethyl 3,3′,3″-phosphine triyl tripropionate (88 g, 0.26 mol) prepared by the above reaction and the concentrated 12 mol/L molar concentration were added to the 250 ml reaction flask. Hydrochloric acid (120ml, 1.44mol) was heated to 80°C with stirring, the solid was gradually dissolved, and the reaction was continued for 3 hours, stirring and cooling with ice water to separate out a white solid, suction filtration, and the filter cake was recrystallized with distilled water to obtain white crystals, namely three. (2-carboxyethyl) phosphine hydrochloride, dried, weighed 57.2g, yield 76.9%.mp174-176℃.
    The nuclear magnetic data are as follows: 1HNMR (D2O, 400MHz): δ=2.57 (dt, 6H), 2.88 (dt, 6H).

Reference

  1.  TCEP technical information, from Interchim
  2. 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”
  3. [Chinese invention, Chinese invention authorization] CN201310173962.2 The preparation method of tris(2-carbonylethyl)phosphonium hydrochloride [publication]/the preparation method of tris(2-carboxyethyl)phosphonium hydrochloride [authorization]

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