Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H15O6P.ClH |
| Molecular Weight | 286.647 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.OC(=O)CCP(CCC(O)=O)CCC(O)=O
InChI
InChIKey=PBVAJRFEEOIAGW-UHFFFAOYSA-N
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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C9H15O6P |
| Molecular Weight | 250.1856 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Tris(2-carboxyethyl)phosphine or TCEP is a potent, versatile, odorless, thiol-free reducing agent with broad application to protein and other research involving reduction of disulfide bonds. Because TCEP does not contain thiols, it does not have to removed from solutions before performing reactions involving maleimide labeling or cross-linking reagents. TCEP may be used as a substitute for DTT or 2-mercaptoethanol (2-ME) in reducing sample loading buffer for SDS-PAGE. One strategy for labeling antibodies involves reducing disulfide bonds in the hinge region of IgG molecules without also reducing those connecting heavy and light chains.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Membrane reinsertion of a myristoyl-peptidyl anchored extracellular domain growth hormone receptor. | 2007-02 |
|
| De novo sequencing and disulfide mapping of a bromotryptophan-containing conotoxin by Fourier transform ion cyclotron resonance mass spectrometry. | 2006-12-01 |
|
| Determination of total tiopronin in human plasma by LC-ESI-MS using tris (2-carboxy-ethyl) phosphine as reducing reagent and methyl acrylate as derivatization reagent for the thiol group. | 2006-11-21 |
|
| Detection of reversible protein thiol modifications in tissues. | 2006-11-15 |
|
| Synthesis and characterization of a novel class of reducing agents that are highly neuroprotective for retinal ganglion cells. | 2006-11 |
|
| Structural basis for a Munc13-1 homodimer to Munc13-1/RIM heterodimer switch. | 2006-07 |
|
| Amide H/2H exchange reveals a mechanism of thrombin activation. | 2006-06-27 |
|
| Proteome-level display by 2-dimensional chromatography of extracellular matrix-dependent modulation of the phenotype of bladder cancer cells. | 2006-06-02 |
|
| Fluorescent labeling of RAFT-generated poly(N-isopropylacrylamide) via a facile maleimide-thiol coupling reaction. | 2006-05 |
|
| Fourier transform mass spectrometry: a powerful tool for toxin analysis. | 2006-05 |
|
| Knock-out of SO1377 gene, which encodes the member of a conserved hypothetical bacterial protein family COG2268, results in alteration of iron metabolism, increased spontaneous mutation and hydrogen peroxide sensitivity in Shewanella oneidensis MR-1. | 2006-04-06 |
|
| Testing electrostatic complementarity in enzyme catalysis: hydrogen bonding in the ketosteroid isomerase oxyanion hole. | 2006-04 |
|
| GEA3162, a nitric oxide-releasing agent, activates non-store-operated Ca2+ entry and inhibits store-operated Ca2+ entry pathways in neutrophils through thiol oxidation. | 2006-03-27 |
|
| Reduction of proteins during sample preparation and two-dimensional gel electrophoresis of woody plant samples. | 2006-03 |
|
| Investigation of cytotoxic, genotoxic, mutagenic, and estrogenic effects of the flame retardants tris-(2-chloroethyl)-phosphate (TCEP) and tris-(2-chloropropyl)-phosphate (TCPP) in vitro. | 2006-02-20 |
|
| Multi residue screening of intact testosterone esters and boldenone undecylenate in bovine hair using liquid chromatography electrospray tandem mass spectrometry. | 2006-01-02 |
|
| Modulation of inhibitory glycine receptors in cultured embryonic mouse hippocampal neurons by zinc, thiol containing redox agents and carnosine. | 2006 |
|
| Characterization of the redox and metal binding activity of BsSco, a protein implicated in the assembly of cytochrome c oxidase. | 2005-12-27 |
|
| Distinct effects of N-ethylmaleimide on formyl peptide- and cyclopiazonic acid-induced Ca2+ signals through thiol modification in neutrophils. | 2005-11-01 |
|
| Neuroprotective effect of sulfhydryl reduction in a rat optic nerve crush model. | 2005-10 |
|
| Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria. | 2005-10 |
|
| Increased sensitivity of amino-arm truncated betaA3-crystallin to UV-light-induced photoaggregation. | 2005-09 |
|
| The genomics of disulfide bonding and protein stabilization in thermophiles. | 2005-09 |
|
| Anomalous electrophoretic behavior of a very acidic protein: ribonuclease U2. | 2005-09 |
|
| A conserved mechanism for sulfonucleotide reduction. | 2005-08 |
|
| Taurine chloramine, an oxidant derived from neutrophils, induces apoptosis in human B lymphoma cells through mitochondrial damage. | 2005-06-03 |
|
| A "de-streaking" method for two-dimensional electrophoresis using the reducing agent tris(2-carboxyethyl)-phosphine hydrochloride and alkylating agent vinylpyridine. | 2005-05 |
|
| Induction of effective and antigen-specific antitumour immunity by a liposomal ErbB2/HER2 peptide-based vaccination construct. | 2005-04-25 |
|
| Stimulation of intracellular Ca2+ elevation in neutrophils by thiol-oxidizing phenylarsine oxide. | 2005-04-15 |
|
| Chymotrypsin responsive hydrogel: application of a disulfide exchange protocol for the preparation of methacrylamide containing peptides. | 2005-03-15 |
|
| Optimizing the connectivity in disulfide-rich peptides: alpha-conotoxin SII as a case study. | 2005-03-01 |
|
| Monitoring of unfolding and refolding in fungal phytase (phyA) by dynamic light scattering. | 2005-02-25 |
|
| Kinetics of swelling of polyether-modified poly(acrylic acid) microgels with permanent and degradable cross-links. | 2005-02-15 |
|
| Mercury compounds disrupt neuronal glutamate transport in cultured mouse cerebellar granule cells. | 2005-02-15 |
|
| Hybridization dependent cleavage of internally modified disulfide-peptide nucleic acids. | 2005-02-01 |
|
| Silyl protecting groups for oligonucleotide synthesis removed by a ZnBr2 treatment. | 2005 |
|
| Dissociation of human copper-zinc superoxide dismutase dimers using chaotrope and reductant. Insights into the molecular basis for dimer stability. | 2004-12-24 |
|
| New water-soluble phosphines as reductants of peptide and protein disulfide bonds: reactivity and membrane permeability. | 2004-12-07 |
|
| A novel method for coupling doxorubicin to lactosaminated human albumin by an acid sensitive hydrazone bond: synthesis, characterization and preliminary biological properties of the conjugate. | 2004-12 |
|
| Mechanisms of N-methyl-D-aspartate receptor inhibition by melatonin in the rat striatum. | 2004-11 |
|
| In vitro studies on thioether bond formation between Hydrogenobacter thermophilus apocytochrome c(552) with metalloprotoporphyrin derivatives. | 2004-10-29 |
|
| A differential assay for the reduced and oxidized states of metallothionein and thionein. | 2004-10-01 |
|
| Mechanism of cysteine desulfurase Slr0387 from Synechocystis sp. PCC 6803: kinetic analysis of cleavage of the persulfide intermediate by chemical reductants. | 2004-09-28 |
|
| Identification of transthyretin variants by sequential proteomic and genomic analysis. | 2004-09 |
|
| Detection of genetic variants of transthyretin by liquid chromatography-dual electrospray ionization fourier-transform ion-cyclotron-resonance mass spectrometry. | 2004-09 |
|
| HPLC simultaneous analysis of thiols and disulfides: on-line reduction and indirect fluorescence detection without derivatization. | 2004-08 |
|
| [Reversed-phase high performance liquid chromatographic behavior of unfolding procedure of Huwentoxin-V]. | 2004-07 |
|
| Coupling of metal containing homing devices to liposomes via a maleimide linker: use of TCEP to stabilize thiol-groups without scavenging metals. | 2004 |
|
| Determination of free and total cyst(e)ine in plasma of dogs and cats. | 2004 |
|
| An unusual cleavage reaction of a peptide observed during dithiotreitol and tris(2-carboxyethyl)phosphine reduction: application to sequencing of HpTx2 spider toxin using nanospray tandem mass spectrometry. | 2004 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:24:36 GMT 2025
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admin
on
Mon Mar 31 22:24:36 GMT 2025
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| Record UNII |
H49AAM893K
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| Record Status |
Validated (UNII)
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| Record Version |
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2734570
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DTXSID10370367
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H49AAM893K
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51805-45-9
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m10492
Created by
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PRIMARY | Merck Index |