CAS 402-71-1

Nα-Tosil-L-fenilalanina clorometil chetone

Descrizione:

Nα-Tosil-L-fenilalanina clorometil chetone, comunemente noto come TPCK, è un composto organico sintetico utilizzato principalmente come inibitore delle proteasi nella ricerca biochimica. Presenta un gruppo tosile, che ne migliora la reattività e la solubilità, e un moiety di chetone clorometilico che è cruciale per il suo meccanismo d'azione. TPCK è noto per la sua capacità di inibire selettivamente le proteasi seriniche, rendendolo prezioso negli studi che coinvolgono la cinetica enzimatica e le interazioni proteiche. Il composto è tipicamente un solido bianco a bianco sporco ed è solubile in solventi organici come il dimetilsolfossido (DMSO) e l'etanolo, ma meno solubile in acqua. La sua struttura gli consente di formare legami covalenti con il sito attivo delle proteasi target, bloccando così la loro attività. TPCK è spesso utilizzato nella purificazione e caratterizzazione di varie enzimi, in particolare nel contesto dello studio delle proteasi virali e di altre applicazioni correlate in biologia molecolare e biochimica. Le condizioni adeguate di manipolazione e stoccaggio sono essenziali a causa della sua natura reattiva e dei potenziali pericoli associati al suo gruppo clorometilico.

Formula: C₁₇H₁₈ClNO₃S

InChI: InChI=1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1

InChI key: InChIKey=MQUQNUAYKLCRME-INIZCTEOSA-N

SMILES: [C@H](NS(=O)(=O)C1=CC=C(C)C=C1)(CC2=CC=CC=C2)C(CCl)=O

Sinonimi:

• (S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide
• <span class="text-smallcaps">L</span>-1-Chloro-3-tosylamidyl-4-phenyl-2-butanone
• <span class="text-smallcaps">L</span>-1-Chloro-4-phenyl-3-p-tolylsulfonamidobutan-2-one
• <span class="text-smallcaps">L</span>-1-Chloro-4-phenyl-3-toluene-p-sulfonamido-2-butanone
• <span class="text-smallcaps">L</span>-1-Tosylamide-2-phenylethylchloromethyl ketone
• <span class="text-smallcaps">L</span>-1-Tosylamido-2-phenylethyl chloromethyl ketone
• <span class="text-smallcaps">L</span>-Tolylsulfonylphenylalanyl chloromethyl ketone
• Benzenesulfonamide, N-((1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-
• Benzenesulfonamide, N-(3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-, (S)-
• Brn 2895215
• L-1-Tosylamido-2-phenylethyl chloromethyl ketone
• N-(4-chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide
• N-(p-Toluenesulfonyl)-<span class="text-smallcaps">L</span>-phenylalanylchloromethane
• N-Tosyl-<span class="text-smallcaps">L</span>-phenylalaninechloromethane
• N-Tosyl-<span class="text-smallcaps">L</span>-phenylalanyl chloromethyl ketone
• N-Tosyl-<span class="text-smallcaps">L</span>-phenylalanylchloromethane
• N-Tosyl-L-phenylalanine chloromethyl ketone
• N-Tosyl-L-phenylalanyl Chloromethyl Ketone
• N-Tosylphenylalanine chloromethyl ketone
• N-[(1S)-3-Chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylbenzenesulfonamide
• N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
• N-α-Tosyl-<span class="text-smallcaps">L</span>-phenylalanylchloromethane
• N^α-Tosyl-<span class="text-smallcaps">L</span>-phenylalanine chloromethyl ketone
• Tosylphenylalanine chloromethyl ketone
• Tosylphenylalanyl chloromethyl ketone
• Tosylphenylalanylchloromethane
• Tpck
• l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide
• p-Toluenesulfonamide, N-(alpha-(chloroacetyl)phenethyl)-, (-)-
• p-Toluenesulfonamide, N-[α-(chloroacetyl)phenethyl]-, <span class="text-smallcaps">L</span>-
• α-N-Tosyl-<span class="text-smallcaps">L</span>-phenylalanine chloromethyl ketone
• p-Toluenesulfonamide, N-[α-(chloroacetyl)phenethyl]-, L-

Tos-Phe-chloromethylketone

CAS: 402-71-1

TPCK irreversibly inhibits α-chymotrypsin, chymotrypsin-like serine proteases, and several cysteine proteases. Additionally, TPCK was shown to affect physiological events as proliferation and apoptosis in certain systems.

Formula: C₁₇H₁₈ClNO₃S

Purezza: > 98%

Colore e forma: White Powder

Peso molecolare: 351.85

Ref: 01-4000836

N-Tosyl-L-phenylalanine chloromethyl ketone

CAS: 402-71-1

Formula: C₁₇H₁₈ClNO₃S

Purezza: 97%

Colore e forma: Solid

Peso molecolare: 351.8477

Ref: IN-DA00I7W7

TPCK

CAS: 402-71-1

TPCK

Purezza: ≥95%

Peso molecolare: 351.85g/mol

Ref: 54-BUP11871

N-p-Tosyl-L-phenylalanine chloromethyl ketone

CAS: 402-71-1

Formula: C₁₇H₁₈ClNO₃S

Purezza: (TLC) ≥ 98.0%

Colore e forma: White to off-white powder

Peso molecolare: 351.85

Ref: 7W-GL8823

TPCK

CAS: 402-71-1

TPCK is an irreversible inhibitor of chymotrypsin-like proteases that affect cell proliferation, apoptosis, and tumorigenesis

Formula: C₁₇H₁₈ClNO₃S

Purezza: 97.33%

Colore e forma: Powder

Peso molecolare: 351.85

Ref: TM-T8350

Tosyl-L-Phenylalanine chloromethylketone

CAS: 402-71-1

Formula: C₁₇H₁₈ClNO₃S

Purezza: 97%

Colore e forma: Solid

Peso molecolare: 351.85

Ref: 10-F493163

N-α-Tosyl-L-phenylalanylchloromethane

Prodotto controllato

CAS: 402-71-1

Applications N-α-Tosyl-L-phenylalanylchloromethane is a proteinase inhibitors with apoptotic function. Studies have shown that it induces caspase-dependent apoptosis in Epstein-Barr virus (EBV)-transformed human B cell lines with release of pro-apoptotic proteins from mitochondria. It also results in down-regulation of the anti-apoptotic proteins and caspase-dependent cleavage of two anti-apoptotic proteins. It promotes dephosphorylation of p53 on serine residues.
References Jitkaew, S. et al.: J. Bio. Chem., 284, 27827 (2009); Kim, K. et al.: Biochem. Biophys. Res. Comm., 306, 954 (2003); Griscavage, J. et al.: Biochem. Biophys. Res. Comm., 215, 721 (1995)

Formula: C₁₇H₁₈ClNO₃S

Colore e forma: Neat

Peso molecolare: 351.848

Ref: TR-T686000