TCEP (TRIS ( 2- CARBOXYETHYL) PHOSPHINE )
TRIS (2-CARBOXYETHYL) PHOSPHINE
CAS Number: 51805-45-9
Synonym: TCEP; Tris-(2-Carboxyethyl)phosphine; Hydrochloride (TCEP);51805-45-9; Tris(2-carboxyethyl)phosphine hydrochloride; TCEP HCl; 3,3′,3”-Phosphinetriyltripropanoic acid hydrochloride; TCEP Hydrochloride; TCEP ; Tris(2-carboxyethyl)phosphine; Tris (2-Carboxyethyl) phosphine Hydrochloride; ≥98 %; Tris(2-carboxyethyl)phosphine; TCEP*HCL;TCEP HCL;0.5M TCEP;500 MM TCEP;TCEP Solution;TCEP, HYDROCHLORIDE;TCEP-HCl, OMniPur(R);Tris(carboxyethyl)phosphine.HC;Tris (carboxyethyl)phosphine HCl;Protein And Peptide Recombination; Tris(2-carboxyethyl)phosphine hydrochloride, 98%; TCEP HCl ; Tris(2-carboxyethyl)phosphine hydrochloride solution from Sigma-Aldrich; Tris(2-carboxyethyl)phosphine; 3,3′,3”-phosphinylidynetris-propanoic acid, monohydrochloride; 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; TCEP Tris(2-carboxyethyl)phosphine; 3,3′,3”-PHOSPHINETRIYL-TRIPROPIONIC ACID HYDROCHLORIDE; 3,3′,3”-PHOSPHINIDYNE-TRIPROPIONIC ACID HYDROCHLORIDE; TCEP; TCEP HCL; TCEP*HCL; TCEP, HYDROCHLORIDE; TRI(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE; TRIS(2-CARBOXYETHYL)PHOSPHINE, HCL; TRIS(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE; TRIS(CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE; TRIS(CARBOXYETHYL)PHOSPHINE &; 0.5M TCEP; TRIS(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE 99%; TRIS-(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE (TCEP HCL); Tris(2-carboxyethyl)phosphine-D16DCl; Tris-(2-carboxyethy)phosphine hydrochloride; Tris(2-carboxyethyl)phosphine,hydrochloride,99%; Tris(2-carboxyethyl)phosphonium Hydrochloride; TRIS-(2-CARBOXYETHYL)PHOSPHINE HYDROCHLORIDE (TCEP); 3,3′,3”-Phosphinidynetrispropanoic Acid Hydrochloride; 3,3′,3”-Phosphinidynetrispropanoic Acid Hydrochloride; Tris(2-carboxyethyl)phosphine Hydrochloride; Tris(carboxyethyl)phosphine Hydrochloride;Propanoic acid, 3,3′,3”-phosphinylidynetris-,; hydrochloride (1:1); Tcep HCl; Tcep hydrochloride; Tcep hydrochloride [MI]; Tris(2-carboxyethyl)phosphine hydrochloride; UNII-H49AAM893K; TRS 2 CARBOXY ETHYL PHOSPHATE; tris 2- carboxyethyl phosphate; tris 2 karboksietil fosfin; tris 2 karboksietil phosphin; karboksietil, fosfin; carboxyethyl, phosphine; carboxyethl phosphine.
Introduced in the late 1980s as a reducing reagent, Tris (2-carboxyethyl) phosphine (TCEP) has now become one of the most widely used protein reductants. To date, only a few studies on its side reactions have been published. We report the observation of a side reaction that cleaves protein backbones under mild conditions by fracturing the cysteine residues, thus generating heterogeneous peptides containing different moieties from the fractured cysteine. The peptide products were analyzed by high performance liquid chromatography and tandem mass spectrometry (LC/MS/MS). Peptides with a primary amine and a carboxylic acid as termini were observed, and others were found to contain amidated or formamidated carboxy termini, or formylated or glyoxylic amino termini. Formamidation of the carboxy terminus and the formation of glyoxylic amino terminus were unexpected reactions since both involve breaking of carbon-carbon bonds in cysteine.Handling, Storage, and Precautions: store at 2-8 °C; -20 °C for long‐term storage. Solid TCEP is stable in air for several months. TCEP is also stable in aqueous solution under both acidic and basic conditions, but is neither particularly stable in phosphate buffers, especially at neutral pH, nor in the presence of a metal chelator, such as EGTA. Therefore, if TCEP is to be used in PBS buffers, working solutions should be prepared immediately before use. TCEP·HCl is an irritant to the eyes, skin, respiratory tract, and digestive tract. Minimize dust generation and accumulation; avoid contact with the eyes, skin, and clothing. Avoid ingestion and inhalation. Acid-base properties and metal-binding abilities of tris(2-carboxyethyl)phosphine (TCEP), a newly introduced thiol group protectant, were studied in solution, using potentiometry, 1H and 31P NMR, and UV-vis spectroscopy, and also in the solid state by X-ray diffraction. Stability constants of complexes of the P-oxide of TCEP (TCEPO) were established by potentiometry. The list of metal ions studied included Ni(II), Cu(II), Zn(II), Cd(II), and Pb(II). Cu(II) catalyzed oxidation of TCEP to TCEPO. For all other systems ML complexes were found as major species at Pb(II). Cu(II) catalyzed oxidation of TCEP to TCEPO. For all other systems ML complexes were found as major species at neutral pH with TCEP and TCEPO. Monoprotonated MHL species were also detected in weakly acidic conditions for all TCEP complexes and for the Pb(II) complex of TCEPO, while hydrolytic MH-1L complexes were found for TCEP at the weakly alkaline pH range. The NiL4 complex was found to form at excess of TCEP. Overall, the complexes were found to be rather weak, with log βML values around 3-5 for TCEP and 1.5-2.5 for TCEPO. The phosphorus pKa value for TCEP, 7.68, suggests that it can be a good buffer for studies at physiological pH.
1980’lerin sonunda bir indirgeme reaktifi olarak tantlan Tris (2-karboksietil) fosfin (TCEP) imdi en çok yaygn olarak kullanlan protein indirgeyicileri. Bugüne kadar, yan reaksiyonlar hakknda sadece birkaç çalma yaynlanmtr. Bildiriyoruz sistein kalntlarn parçalayarak, hafif koullar altnda protein omurgalarn bölen bir yan reaksiyonun gözlemlenmesi, böylece krk sisteinden farkl parçalar içeren heterojen peptitler üretilir. Peptit ürünleri Yüksek performansl sv kromatografisi ve tandem kütle spektrometresi (LC / MS / MS) ile analiz edilmitir. Birincil amin ile peptitler ve termin olarak bir karboksilik asit gözlenmi ve dierleri amitlenmi veya formamide karboksi terminali ihtiva ettii bulunmutur, veya formile veya glioksilik amino terminali. Karboksi terminusun formamidasyonu ve glioksilik amino oluumu Terminus, beklenmedik reaksiyonlard, çünkü her ikisi de sisteinde karbon-karbon balarnn krlmasn içerir. Önlemler: 2-8 ° C’de saklayn; Uzun süreli depolama için -20 ° C. Kat TCEP, birkaç ay boyunca havada stabildir. TCEP ayrca hem asidik hem de bazik koullar altnda sulu çözeltide stabildir, ancak fosfat tamponlarnda özellikle kararl deildir, özellikle nötr pH’ta, ne EGTA gibi bir metal elatörü varlnda. Bu nedenle, eer TCEP PBS’de kullanlacaksa Tamponlar, çalma solüsyonlar kullanmdan hemen önce hazrlanmaldr. TCEP · HCI göz, cilt, solunum yolu ve sindirim sistemi. Toz oluumunu ve birikmesini en aza indirir; Göz, cilt ve giyim. Yutma ve solumaktan kaçnn. Tris (2-karboksietil) fosfinlerin asit özellikleri ve metal balama yetenekleri yeni gelitirilen bir tiyol grubu koruyucu (TCEP), potansiyometri, 1H ve 31P NMR ve UV kullanarak çözelti üzerinde çalld. X-n krnm ile spectvis spektroskopisi ve ayrca kat halde. P-oksit komplekslerinin stabilite sabitleri TCEP (TCEPO) potansiyometri ile kurulmutur. ncelenen metal iyonlarn listesi Ni (II), Cu (II), Zn (II), Cd (II) vPb (ll). Cu (II), TCEP’nin TCEPO’ya oksidasyonunu katalize etti. Dier tüm sistemler için ML kompleksleri ana türler olarak bulunmutur.TCEP ve TCEPO ile nötr pH. Monofrotonlu MHL türleri de tüm TCEP için zayf asidik koullarda tespit edilmitir.Kompleksler ve TCEPO’nun Pb (II) kompleksi için, zayf alkali olarak TCEP için hidrolitik MH-1L kompleksleri bulunmutur pH aral. NiL4 kompleksinin TCEP’yi at görülmütür. Genel olarak, komplekslerin oldukça zayf olduu bulunmutur.TCEP için -ML deerleri 3-5 ve TCEPO için 1.5-2.5. TCEP için fosfor pKa deeri, 7.68, bunun olabileceini düündürmektedir.Fizyolojik pH’ta çalmalar için iyi bir tampon.