CAS 402-71-1

Nα-Tosyl-L-phenylalanine chloromethyl ketone

Description:

Nα-Tosyl-L-phenylalanine chloromethyl ketone, commonly referred to as TPCK, is a synthetic organic compound primarily used as a protease inhibitor in biochemical research. It features a tosyl group, which enhances its reactivity and solubility, and a chloromethyl ketone moiety that is crucial for its mechanism of action. TPCK is known for its ability to selectively inhibit serine proteases, making it valuable in studies involving enzyme kinetics and protein interactions. The compound is typically a white to off-white solid and is soluble in organic solvents such as dimethyl sulfoxide (DMSO) and ethanol, but less soluble in water. Its structure allows it to form covalent bonds with the active site of target proteases, thereby blocking their activity. TPCK is often utilized in the purification and characterization of various enzymes, particularly in the context of studying viral proteases and other related applications in molecular biology and biochemistry. Proper handling and storage conditions are essential due to its reactive nature and potential hazards associated with its chloromethyl group.

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

Synonyms:

• (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

Purity: > 98%

Color and Shape: White Powder

Molecular weight: 351.85

Ref: 01-4000836

N-Tosyl-L-phenylalanine chloromethyl ketone

CAS: 402-71-1

Formula: C₁₇H₁₈ClNO₃S

Purity: 97%

Color and Shape: Solid

Molecular weight: 351.8477

Ref: IN-DA00I7W7

TPCK

CAS: 402-71-1

TPCK

Purity: ≥95%

Molecular weight: 351.85g/mol

Ref: 54-BUP11871

N-p-Tosyl-L-phenylalanine chloromethyl ketone

CAS: 402-71-1

Formula: C₁₇H₁₈ClNO₃S

Purity: (TLC) ≥ 98.0%

Color and Shape: White to off-white powder

Molecular weight: 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

Purity: 97.33%

Color and Shape: Powder

Molecular weight: 351.85

Ref: TM-T8350

Tosyl-L-Phenylalanine chloromethylketone

CAS: 402-71-1

Formula: C₁₇H₁₈ClNO₃S

Purity: 97%

Color and Shape: Solid

Molecular weight: 351.85

Ref: 10-F493163

N-α-Tosyl-L-phenylalanylchloromethane

Controlled Product

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

Color and Shape: Neat

Molecular weight: 351.848

Ref: TR-T686000