CAS 402-71-1

Nα-Tosil-L-fenilalanina clorometil cetona

Descripción:

Nα-Tosil-L-fenilalanina clorometil cetona, comúnmente conocido como TPCK, es un compuesto orgánico sintético que se utiliza principalmente como un inhibidor de proteasas en la investigación bioquímica. Presenta un grupo tosilo, que mejora su reactividad y solubilidad, y un moiety de clorometil cetona que es crucial para su mecanismo de acción. TPCK es conocido por su capacidad para inhibir selectivamente las serina proteasas, lo que lo hace valioso en estudios que involucran cinética enzimática e interacciones proteicas. El compuesto es típicamente un sólido blanco a blanco sucio y es soluble en disolventes orgánicos como el dimetilsulfóxido (DMSO) y el etanol, pero menos soluble en agua. Su estructura le permite formar enlaces covalentes con el sitio activo de las proteasas objetivo, bloqueando así su actividad. TPCK se utiliza a menudo en la purificación y caracterización de varias enzimas, particularmente en el contexto del estudio de proteasas virales y otras aplicaciones relacionadas en biología molecular y bioquímica. Las condiciones adecuadas de manejo y almacenamiento son esenciales debido a su naturaleza reactiva y los peligros potenciales asociados con su grupo clorometil.

Fórmula: 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

Clave InChI: InChIKey=MQUQNUAYKLCRME-INIZCTEOSA-N

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

Sinónimos:

• (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.

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: > 98%

Forma y color: White Powder

Peso molecular: 351.85

Ref: 01-4000836

TPCK

CAS: 402-71-1

TPCK

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: ≥95%

Peso molecular: 351.85

Ref: 54-BUP11871

N-Tosyl-L-phenylalanine chloromethyl ketone

CAS: 402-71-1

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: 97%

Forma y color: Solid

Peso molecular: 351.8477

Ref: IN-DA00I7W7

TPCK

CAS: 402-71-1

(S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: 97%

Peso molecular: 351.85

Ref: IN-DG154431

TPCK

CAS: 402-71-1

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

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: 97.33%

Forma y color: Solid

Peso molecular: 351.85

Ref: TM-T8350

N-p-Tosyl-L-phenylalanine chloromethyl ketone

CAS: 402-71-1

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: (TLC) ≥ 98.0%

Forma y color: White to off-white powder

Peso molecular: 351.85

Ref: 7W-GL8823

Tosyl-L-Phenylalanine chloromethylketone

CAS: 402-71-1

Fórmula: C₁₇H₁₈ClNO₃S

Pureza: 97%

Forma y color: Solid

Peso molecular: 351.85

Ref: 10-F493163

N-α-Tosyl-L-phenylalanylchloromethane

Producto controlado

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)

Fórmula: C₁₇H₁₈ClNO₃S

Forma y color: Neat

Peso molecular: 351.848

Ref: TR-T686000