Tris(2-carboxyethyl)phosphine hydrochloride

Tris(2-carboxyethyl)phosphine hydrochloride Basic information
Product Name:Tris(2-carboxyethyl)phosphine hydrochloride
Synonyms:Tris(2-carboxyethyl)phosphine hydrochloride solution,TCEP;TCEP-HCl, OMniPur(R);TRIS(2-CARBOXYETHYL)PHOSPHINE:DCL (TCEP);Tris(carboxyethyl)phosphine.HC;Tris(2-carboxyethyl)phosphine hydrochloride, 0.5M soln in water;Tris(2-carboxyethyl)phosphine hydrochloride, 98% 1GR;Tris(2-carboxyethyl)phosphine hydrochloride, 95%, 0.5M soln. in water;500 MM TCEP
CAS:51805-45-9
MF:C9H15O6P.ClH
MW:286.65
EINECS:629-759-1
Product Categories:buffer;Life Science Chemical Reagents;Ligand;Aliphatics;Phosphorylating and Phosphitylating Agents;organophosphorus ligand;Phosphonium Salts;51805-45-9
Mol File:51805-45-9.mol
Tris(2-carboxyethyl)phosphine hydrochloride Structure
Tris(2-carboxyethyl)phosphine hydrochloride Chemical Properties
Melting point 177 °C
density 1.041 g/mL at 25 °C
refractive index n20/D 1.367
storage temp. 2-8°C
solubility H2O: 50 mg/mL
pka7.66(at 25℃)
form powder
color white
PH7.0(aqueous solution; pH was adjusted with ammonium hydroxide)
Water Solubility Soluble in water and methanol.
λmaxλ: 260 nm Amax: 0.05
λ: 280 nm Amax: 0.03
Sensitive Moisture Sensitive
Merck 14,9085
BRN 3724376
Stability:Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month.
InChIKeyPBVAJRFEEOIAGW-UHFFFAOYSA-N
CAS DataBase Reference51805-45-9(CAS DataBase Reference)
Safety Information
Hazard Codes C,Xi
Risk Statements 36/38-36/37/38-34
Safety Statements 26-37/39-36/37/39-27-45
RIDADR UN 3261 8/PG 2
WGK Germany 2
10
TSCA No
HazardClass 8
PackingGroup III
HS Code 29319090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Tris(2-carboxyethyl)phosphine hydrochloride Usage And Synthesis
DescriptionTCEP HCl (51805-45-9) is a reagent for selective reduction of disulfides in aqueous solutions1-3?with distinct advantages over DTT which are application specific3. For example, spin labels are more stable with TCEP than DTT, Ni2+?(leached from affinity columns) causes rapid oxidation of DTT with no effect on TCEP and for long term storage of proteins TCEP is more stable than DTT with no metal chelator (EGTA) present but DTT is more stable in the presence of metal chelators.3
Chemical PropertiesWhite Crystalline Solid
UsesTCEP (Tris(2-carboxyethyl)phosphine hydrochloride) is an alternative which is not pungent, more stable and works even at low pH. It is more selective, i.e. do not reduce metals and buried disulfides.
UsesBiochemical tool for selective reduction of disulfide bridges at low pH; reductant for redox assays.
UsesReducing agent, specific for disulfidesTris(2-carboxyethyl)phosphine hydrochloride is widely used as a reducing agent to reduce disulfide bonds in proteins and trans-4,5-dihydroxy-1,2-dithiane. It is involved in the reduction of sulfoxides, sulfonyl chlorides, N-oxides, and azides. It plays an important role in the tissue homogenization process for RNA isolation. It acts as a chelating agent and forms complexes with various heavy metal ions such as Zn(II), Cd(II), Pb(II), and Ni(II). Furthermore, it is useful in the labeling of cysteine residues with maleimides.
PreparationThe preparation of Tris(2-carboxyethyl)phosphine hydrochloride is as follows:Trimethyl 3,3 ', 3 "-phosphine triphenylpropionate (92.5g, 0.28mol) prepared as described above was added to a 250 ml reaction flask under mechanical stirring conditions and a molar ratio of 12mol/(120ml, 1.44mol), the mixture was heated to 90°C, the solid gradually dissolved, continue to heat the reaction 4h, stirring and cooling with ice water, precipitation of white solid, filter, filter cake with distilled water to get white (2-carboxyethyl) phosphine hydrochloride, dried, weighing 61.3g, yield 82.4%
General DescriptionTris (2-carboxyethyl) phosphine (TCEP) is very effective in cleaving disulfide bonds in aqueous solution. It dissolves in water and is odorless, unlike other trialkylphosphines (tributylphosphine). It is also less toxic than 2-mercaptoethanol. These advantages make it better than the other reducing agents.
Biochem/physiol ActionsTris(2-carboxyethyl)phosphine hydrochloride solution reduces the disulfide bonds and leaves other functional groups intact in proteins.
References1) Fischer?et al.?(1993),?In situ reduction suitable for matrix-assisted laser desorption/ionization and liquid secondary ionization using tris(2-carboxyethyl)phosphine; Rapid Commun. Mass Spectrom.,?7?225 2) Kirley?et al.?(1989),?Reduction and fluorescent labeling of cyst(e)ine-containing proteins for subsequent structural analysis; Anal. Biochem.,?180?231 3) Getz?et al. (1999),?A comparison between the sulfhydryl reductants tris(2-carboxyethyl)phosphine and dithiothreitol for use in protein biochemistry; Anal. Biochem.,?273?73
Tris(2-carboxyethyl)phosphine hydrochloride Preparation Products And Raw materials
Fudosteine 4-Ethylaniline TRIS(3-METHOXYPHENYL)PHOSPHINE 2-Bromoethanol Phosphoric acid Tris(2-chloroethyl) phosphate Tris(4-fluorophenyl)phosphine Hydroxyethyl Cellulose Maleimide TRIS(2-METHOXYPHENYL)PHOSPHINE 4'-Hydroxyacetophenone TRIS(4-METHOXYPHENYL)PHOSPHINE SPINETORAM Decamethylcyclopentasiloxane Thiourea TRIS(HYDROXYPROPYL)PHOSPHINE Tris(2-carboxyethyl)phosphine hydrochloride Phosphine

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.