Home Carboxys Tris(2-carboxyethyl)phosphine, HCl

Tris(2-carboxyethyl)phosphine, HCl

CAS No.:
51805-45-9
Catalog Number:
AG003V70
Molecular Formula:
C9H16ClO6P
Molecular Weight:
286.6465
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%
In Stock USA
United States
$13
- +
5g
98%
In Stock USA
United States
$36
- +
25g
98%
In Stock USA
United States
$150
- +
100g
98%
In Stock USA
United States
$450
- +
Product Description
Catalog Number:
AG003V70
Chemical Name:
Tris(2-carboxyethyl)phosphine, HCl
CAS Number:
51805-45-9
Molecular Formula:
C9H16ClO6P
Molecular Weight:
286.6465
MDL Number:
MFCD00145469
IUPAC Name:
3-[bis(2-carboxyethyl)phosphanyl]propanoic acid;hydrochloride
InChI:
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
SMILES:
OC(=O)CCP(CCC(=O)O)CCC(=O)O.Cl
UNII:
H49AAM893K
UN Number:
3082
Properties
Complexity:
222  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
286.037g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
286.645g/mol
Monoisotopic Mass:
286.037g/mol
Rotatable Bond Count:
9  
Topological Polar Surface Area:
112A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
The combination of in silico and in vivo approaches for the investigation of disrupting effects of tris (2-chloroethyl) phosphate (TCEP) toward core receptors of zebrafish. Chemosphere 20170201
Developmental exposure of zebrafish larvae to organophosphate flame retardants causes neurotoxicity. Neurotoxicology and teratology 20160101
TPP and TCEP induce oxidative stress and alter steroidogenesis in TM3 Leydig cells. Reproductive toxicology (Elmsford, N.Y.) 20151101
Neurotoxicological and thyroid evaluations of rats developmentally exposed to tris(1,3-dichloro-2-propyl)phosphate (TDCIPP) and tris(2-chloro-2-ethyl)phosphate (TCEP). Neurotoxicology and teratology 20150101
Toxicity of TDCPP and TCEP on PC12 cell: changes in CAMKII, GAP43, tubulin and NF-H gene and protein levels. Toxicology letters 20140616
Cisplatin handover between copper transporters: the effect of reducing agents. Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry 20140601
Methylation of arsenic by recombinant human wild-type arsenic (+3 oxidation state) methyltransferase and its methionine 287 threonine (M287T) polymorph: Role of glutathione. Toxicology and applied pharmacology 20121001
Design and synthesis of cleavable biotinylated dideoxynucleotides for DNA sequencing by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Analytical biochemistry 20120815
On-line cleavage of disulfide bonds by soluble and immobilized tris-(2-carboxyethyl)phosphine using sequential injection analysis. Talanta 20120715
Levels and distributions of organophosphate flame retardants and plasticizers in sediment from Taihu Lake, China. Environmental toxicology and chemistry 20120701
Differential affinity of BsSCO for Cu(II) and Cu(I) suggests a redox role in copper transfer to the Cu(A) center of cytochrome c oxidase. Biochimica et biophysica acta 20120601
Analytical measurement of discrete hydrogen sulfide pools in biological specimens. Free radical biology & medicine 20120601
Endothelial cell surface expression of protein disulfide isomerase activates β1 and β3 integrins and facilitates dengue virus infection. Journal of cellular biochemistry 20120501
Reverse thioether ligation route to multimeric peptide antigens. Organic & biomolecular chemistry 20120421
Reducing agents affect inhibitory activities of compounds: results from multiple drug targets. Analytical biochemistry 20120401
Gold nanoparticle extraction followed by o-phthaldialdehyde derivatization for fluorescence sensing of different forms of homocysteine in plasma. Talanta 20120315
Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets. Journal of medicinal chemistry 20120223
Quantitative analysis of tris(2-carboxyethyl)phosphine by anion-exchange chromatography and evaporative light-scattering detection. Journal of pharmaceutical and biomedical analysis 20120205
Cu(ii)- and disulfide bonds-induced stabilization during the guanidine hydrochloride- and thermal-induced denaturation of NAD-glycohydrolase from the venom of Agkistrodon acutus. Metallomics : integrated biometal science 20120201
'Outer-sphere to inner-sphere' redox cycling for ultrasensitive immunosensors. Analytical chemistry 20120117
Exploring the smallest active fragment of HsQSOX1b and finding a highly efficient oxidative engine. PloS one 20120101
Is the PentaBDE replacement, tris (1,3-dichloro-2-propyl) phosphate (TDCPP), a developmental neurotoxicant? Studies in PC12 cells. Toxicology and applied pharmacology 20111101
Chemical modification of proteins to improve the accuracy of their relative molecular mass determination by electrophoresis. Electrophoresis 20111001
Occurrence and suitability of sucralose as an indicator compound of wastewater loading to surface waters in urbanized regions. Water research 20110701
Ascorbate as an alternative to thiol additives in native chemical ligation. Chembiochem : a European journal of chemical biology 20110614
Kinetic measurements on single-molecule disulfide bond cleavage. Journal of the American Chemical Society 20110316
Crucial effect of the first CXXC motif of human QSOX 1b on the activity to different substrates. Journal of biochemistry 20110301
Synthesis of histone H3 proteins by a thioacid capture ligation strategy. Chemical communications (Cambridge, England) 20110214
Time-dependent, protein-directed growth of gold nanoparticles within a single crystal of lysozyme. Nature nanotechnology 20110201
P0 (protein zero) mutation S34C underlies instability of internodal myelin in S63C mice. The Journal of biological chemistry 20101231
Organophosphate ester flame retardant-induced acute intoxications in dogs. Journal of medical toxicology : official journal of the American College of Medical Toxicology 20101201
Comparative analyses of proteolytic activities in seven species of synanthropic acaridid mites. Archives of insect biochemistry and physiology 20101101
Tracking of antibody reduction fragments by capillary gel electrophoresis during the coupling to microparticles surface. Journal of pharmaceutical and biomedical analysis 20101010
Traceless ligation of cysteine peptides using selective deselenization. Angewandte Chemie (International ed. in English) 20100917
A tris (2-carboxyethyl) phosphine (TCEP) related cleavage on cysteine-containing proteins. Journal of the American Society for Mass Spectrometry 20100501
Cu(I) binding properties of a designed metalloprotein. Journal of inorganic biochemistry 20100301
An improved phenylarsine oxide-affinity method identifies triose phosphate isomerase as a candidate redox receptor protein. Neurochemical research 20100201
Small-molecule reductants inhibit multicatalytic activity of AA-NADase from Agkistrodon acutus venom by reducing the disulfide-bonds and Cu(II) of enzyme. Biopolymers 20100201
Modification of thiol functionalized aptamers by conjugation of synthetic polymers. Bioconjugate chemistry 20100101
Determination of dehydroascorbic acid in mouse tissues and plasma by using tris(2-carboxyethyl)phosphine hydrochloride as reductant in metaphosphoric acid/ethylenediaminetetraacetic acid solution. Biological & pharmaceutical bulletin 20100101
Temporal concentration changes of DEET, TCEP, terbutryn, and nonylphenols in freshwater streams of Hesse, Germany: possible influence of mandatory regulations and voluntary environmental agreements. Environmental science and pollution research international 20090901
TCEP treatment reduces proteolytic activity of BoNT/B in human neuronal SHSY-5Y cells. Journal of cellular biochemistry 20090801
Bovine insulin filaments induced by reducing disulfide bonds show a different morphology, secondary structure, and cell toxicity from intact insulin amyloid fibrils. Biophysical journal 20090422
Amyloid fibrillation of hen egg-white lysozyme is inhibited by TCEP. Biochemical and biophysical research communications 20090417
Protein S-S bridge reduction: a Raman and computational study of lysozyme interaction with TCEP. Physical chemistry chemical physics : PCCP 20090414
Chelator-facilitated chemical modification of IMP-1 metallo-beta-lactamase and its consequences on metal binding. Biochemical and biophysical research communications 20090327
Molecular cloning, overproduction, purification and biochemical characterization of the p39 nsp2 protease domains encoded by three alphaviruses. Protein expression and purification 20090301
Effect of tris-(2-chloroethyl)-phosphate (TCEP) at environmental concentration on the levels of cell cycle regulatory protein expression in primary cultured rabbit renal proximal tubule cells. Chemosphere 20081201
Identification of two inactive forms of the central sulfur cycle protein SoxYZ of Paracoccus pantotrophus. FEBS letters 20081029
Folding strategy to prepare Co(II)-substituted metallo-beta-lactamase L1. Analytical biochemistry 20080715
Enrichment by organomercurial agarose and identification of cys-containing peptides from yeast cell lysates. Analytical chemistry 20080501
Saturation fluorescence labeling of proteins for proteomic analyses. Analytical biochemistry 20080315
Carbonic anhydrase inhibitors: the very weak inhibitors dithiothreitol, beta-mercaptoethanol, tris(carboxyethyl)phosphine and threitol interfere with the binding of sulfonamides to isozymes II and IX. Bioorganic & medicinal chemistry letters 20080315
Dwell time analysis of a single-molecule mechanochemical reaction. Langmuir : the ACS journal of surfaces and colloids 20080219
Oxidative inhibition of protein phosphatase 2A activity: role of catalytic subunit disulfides. Neurochemical research 20071101
Reduction of dehydroascorbic acid at low pH. Journal of biochemical and biophysical methods 20070801
An aptly positioned azido group in the spacer of a protein cross-linker for facile mapping of lysines in close proximity. Chembiochem : a European journal of chemical biology 20070723
Alternative antibody Fab' fragment PEGylation strategies: combination of strong reducing agents, disruption of the interchain disulphide bond and disulphide engineering. Protein engineering, design & selection : PEDS 20070501
Catch-and-release reagents for broadscale quantitative proteomics analyses. Journal of proteome research 20070401
Membrane reinsertion of a myristoyl-peptidyl anchored extracellular domain growth hormone receptor. Endocrinology 20070201
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. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20061121
Synthesis and characterization of a novel class of reducing agents that are highly neuroprotective for retinal ganglion cells. Experimental eye research 20061101
Amide H/2H exchange reveals a mechanism of thrombin activation. Biochemistry 20060627
Fourier transform mass spectrometry: a powerful tool for toxin analysis. Toxicon : official journal of the International Society on Toxinology 20060501
Reduction of proteins during sample preparation and two-dimensional gel electrophoresis of woody plant samples. Proteomics 20060301
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. Toxicology letters 20060220
Characterization of the redox and metal binding activity of BsSco, a protein implicated in the assembly of cytochrome c oxidase. Biochemistry 20051227
Distinct effects of N-ethylmaleimide on formyl peptide- and cyclopiazonic acid-induced Ca2+ signals through thiol modification in neutrophils. Biochemical pharmacology 20051101
Mitochondrial leader sequence--plasmid DNA conjugates delivered into mammalian cells by DQAsomes co-localize with mitochondria. Mitochondrion 20051001
Neuroprotective effect of sulfhydryl reduction in a rat optic nerve crush model. Investigative ophthalmology & visual science 20051001
Anomalous electrophoretic behavior of a very acidic protein: ribonuclease U2. Electrophoresis 20050901
Monitoring of unfolding and refolding in fungal phytase (phyA) by dynamic light scattering. Biochemical and biophysical research communications 20050225
Mercury compounds disrupt neuronal glutamate transport in cultured mouse cerebellar granule cells. Journal of neuroscience research 20050215
Silyl protecting groups for oligonucleotide synthesis removed by a ZnBr2 treatment. Nucleosides, nucleotides & nucleic acids 20050101
Dissociation of human copper-zinc superoxide dismutase dimers using chaotrope and reductant. Insights into the molecular basis for dimer stability. The Journal of biological chemistry 20041224
New water-soluble phosphines as reductants of peptide and protein disulfide bonds: reactivity and membrane permeability. Biochemistry 20041207
A differential assay for the reduced and oxidized states of metallothionein and thionein. Analytical biochemistry 20041001
Mechanism of cysteine desulfurase Slr0387 from Synechocystis sp. PCC 6803: kinetic analysis of cleavage of the persulfide intermediate by chemical reductants. Biochemistry 20040928
Cyclic voltammetric study of the redox system of glutathione using the disulfide bond reductant tris(2-carboxyethyl)phosphine. Bioelectrochemistry (Amsterdam, Netherlands) 20040601
Endogenous reductants support the catalytic function of recombinant rat cyt19, an arsenic methyltransferase. Chemical research in toxicology 20040301
Tris(2-carboxyethyl)phosphine stabilization of RNA: comparison with dithiothreitol for use with nucleic acid and thiophosphoryl chemistry. Analytical biochemistry 20040201
A formula for correlating pKa values determined in D2O and H2O. Journal of inorganic biochemistry 20040101
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. Rapid communications in mass spectrometry : RCM 20040101
Determination of free and total cyst(e)ine in plasma of dogs and cats. Veterinary clinical pathology 20040101
Coupling of metal containing homing devices to liposomes via a maleimide linker: use of TCEP to stabilize thiol-groups without scavenging metals. Journal of drug targeting 20040101
Semisynthesis and application of carboxyfluorescein-labelled biologically active human interleukin-8. Biological chemistry 20031201
Amplification of a reactive oxygen species signal in axotomized retinal ganglion cells. Antioxidants & redox signaling 20031001
The effects of oxidative stress on mitochondrial transmembrane potential in retinal ganglion cells. Antioxidants & redox signaling 20031001
Avian sulfhydryl oxidase is not a metalloenzyme: adventitious binding of divalent metal ions to the enzyme. Biochemistry 20030923
Evidence for intersubunit interactions between S4 and S5 transmembrane segments of the Shaker potassium channel. The Journal of biological chemistry 20030801
Reductive dehalogenation of monobromobimane by tris(2-carboxyethyl)phosphine. Analytical biochemistry 20030715
X-ray absorption spectroscopy of the copper chaperone HAH1 reveals a linear two-coordinate Cu(I) center capable of adduct formation with exogenous thiols and phosphines. The Journal of biological chemistry 20030620
Monitoring of the three organophosphate esters TBP, TCEP and TBEP in river water and ground water (Oder, Germany). Journal of environmental monitoring : JEM 20030401
Human acid sphingomyelinase. European journal of biochemistry 20030301
Effects of phthalic anhydride modification on horseradish peroxidase stability and activity. Biotechnology and bioengineering 20030120
Proteomic study of a model causative agent of harmful red tide, Prorocentrum triestinum I: Optimization of sample preparation methodologies for analyzing with two-dimensional electrophoresis. Proteomics 20020901
On-column tris(2-carboxyethyl)phosphine reduction and IC5-maleimide labeling during purification of a RpoC fragment on a nickel-nitrilotriacetic acid Column. Analytical biochemistry 20020815
Development of a novel method to populate native disulfide-bonded intermediates for structural characterization of proteins: implications for the mechanism of oxidative folding of RNase A. Journal of the American Chemical Society 20020508
Functional properties of the copper-transporting ATPase ATP7B (the Wilson's disease protein) expressed in insect cells. The Journal of biological chemistry 20020111
Reduced redox state allows prolonged survival of axotomized neonatal retinal ganglion cells. Neuroscience 20020101
Occurrence of organophosphate esters in surface water and ground water in Germany. Journal of environmental monitoring : JEM 20011201
Measurement of homocysteine and other aminothiols in plasma: advantages of using tris(2-carboxyethyl)phosphine as reductant compared with tri-n-butylphosphine. Clinical chemistry 20011001
Determination of the disulfide structure of sillucin, a highly knotted, cysteine-rich peptide, by cyanylation/cleavage mass mapping. Biochemistry 20010417
Disulfide bond structure of the AVR9 elicitor of the fungal tomato pathogen Cladosporium fulvum: evidence for a cystine knot. Biochemistry 20010327
Sedimentation studies reveal a direct role of phosphorylation in Smad3:Smad4 homo- and hetero-trimerization. Biochemistry 20010206
A chemical method to isolate hypothalamic nonapeptides by coupling cyst(e)in with bimane. Journal of cellular and molecular medicine 20010101
Cleavage of disulfide bonds leads to inactivation and degradation of the type IIa, but not type IIb sodium phosphate cotransporter expressed in Xenopus laevis oocytes. The Journal of membrane biology 20000715
A micro-method for quantitative determination of acylneuraminic acids from erythrocyte membranes. Hoppe-Seyler's Zeitschrift fur physiologische Chemie 19751101
Properties