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TPCK

Product Name
TPCK
CAS No.
402-71-1
Chemical Name
TPCK
Synonyms
TPCK;L-TPCK;TOS-PHE-CMK;Tos-L-Phe-CMK;TPCK USP/EP/BP;(-)-p-toluenesulfonamid;Tos-L-Phe-Chloromethane;TOS-PHE-CHLOROMETHYLKETONE;N-TOSYL-PHE-CHLOROMETHYLKETONE;Tosylphenylalanylchloromethane
CBNumber
CB0354828
Molecular Formula
C17H18ClNO3S
Formula Weight
351.85
MOL File
402-71-1.mol
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TPCK Property

Melting point:
106-108 °C(lit.)
Boiling point:
509.9±60.0 °C(Predicted)
Density 
1.1350 (rough estimate)
refractive index 
1.6100 (estimate)
storage temp. 
-20°C
solubility 
DMSO: >10 mg/mL stable for several months at 4°C.
form 
powder
pka
8.71±0.50(Predicted)
color 
white
BRN 
2895215
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
CAS DataBase Reference
402-71-1
EPA Substance Registry System
Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl- (402-71-1)
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Safety

Hazard Codes 
Xi
Risk Statements 
37/38-41
Safety Statements 
26-36
RIDADR 
UN 3335
WGK Germany 
3
RTECS 
XT5613500
F 
10-19-21
TSCA 
Yes
HS Code 
29350090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T4376
Product name
N-p-Tosyl-L-phenylalanine chloromethyl ketone
Purity
≥97% (TLC), powder
Packaging
1g
Price
$249
Updated
2024/03/01
Sigma-Aldrich
Product number
616387
Product name
N-p-Tosyl-L-phenylalanine chloromethyl ketone
Purity
Irreversible inhibitor of chymotrypsin.
Packaging
250mg
Price
$85.2
Updated
2024/03/01
TCI Chemical
Product number
T2810
Product name
N-(p-Toluenesulfonyl)-L-phenylalanyl Chloromethyl Ketone
Purity
>95.0%(HPLC)(T)
Packaging
1g
Price
$212
Updated
2021/12/16
TCI Chemical
Product number
T2810
Product name
N-(p-Toluenesulfonyl)-L-phenylalanyl Chloromethyl Ketone
Purity
>95.0%(HPLC)(T)
Packaging
200mg
Price
$72
Updated
2021/12/16
Alfa Aesar
Product number
J60639
Product name
N-(p-Toluenesulfonyl)-L-phenylalanine chloromethyl ketone
Packaging
5g
Price
$619
Updated
2021/12/16
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TPCK Chemical Properties,Usage,Production

Description

TPCK (402-71-1) is an irreversible inhibitor of the serine protease chymotrypsin.1 It also inhibits certain cysteine proteases (bromelain, ficin, papain).1 TPCK inhibited (IC50 = 5 μM) the mitogen-induced activation of pp70s6k, a mitogen-regulated serine/threonine kinase involved in the G1 to S phase transition of the cell cycle.2

Chemical Properties

white crystalline powder

Uses

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.

Definition

ChEBI: The N-tosyl derivative of L-phenylalanyl chloromethyl ketone.

Biochem/physiol Actions

Blocks the LPS- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of iNOS and COX-2 transcription. Blocks activation of pp70s6k by all mitogens. Blocks apoptosis cell lines by inhibiting the processing of caspases in some cell lines and to some stimuli. Also blocks apoptosis initiated by Taxol (in MCF-7 human breast carcinoma cells).

Safety Profile

Experimental reproductive effects. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx, SOx, and Cl-.

References

1) Bond and Butler, (1987) Intracellular proteases; Annu. Rev. Biochem., 56 333 2) Grammer and Blenis (1996) The serine protease inhibitors, tosylphenylalanine chloromethylketone and tosyllysine chloromethylketone, potently inhibit pp70s6k activation; J. Biol. Chem., 271 23650

TPCK Preparation Products And Raw materials

Raw materials

Preparation Products

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TPCK Suppliers

Belgium 1 Canada 1 China 89 Germany 6 India 4 Japan 4 South Korea 1 Switzerland 1 United Kingdom 3 United States 27 Global 137
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View Lastest Price from TPCK manufacturers

Career Henan Chemical Co
Product
Tosyl phenylalanyl chloromethyl ketone 402-71-1
Price
US $1.00/kg
Min. Order
1kg
Purity
95%-99%
Supply Ability
1000kg
Release date
2018-12-25

402-71-1, TPCKRelated Search:

2-Methyl-4-isothiazolin-3-one N-Cbz-Nortropinone 1-N-PHENYL-PIPERIDIN-4-ONE N-BOC-L-leucylglycyl-arginine-p-nitroanilide hydrochloride Ethyl N-benzoyl-L-tyrosinate BAA TOS-ARG-OME HCL TLCK N-Benzoyl-DL-arginine-4-nitroanilide hydrochloride Ethyl N-benzoyl-L-argininate hydrochloride BUTEIN Trypsin TPCK IMMOBILIZED TRYPSIN, TPCK,TPCK TRYPSIN,TRYPSIN, TPCK TREATED TRYPSIN TPCK TREATED FROM BOVINE PANCREA TRYPSIN, TPCK TREATED, FROM BOVINE PANCREAS TPCK-TRYPSIN AGAROSE TRYPSIN FROM BOVINE PANCREAS TPCK TREATE

  • L-1-TOSYLAMIDE-2-PHENYLETHYL-CHLOROMETHYL KETONE
  • L-1-P-TOSYLAMINO-2-PHENYLETHYL CHLOROMETHYL KETONE
  • L-1-CHLORO-3-(4-TOSYLAMIDO)-4-PHENYL-2-BUTANONE
  • L-1-CHLORO-3-TOSYLAMIDO-4-PHENYL-2-BUTANONE
  • L-1-4'-TOSYLAMINO-2-PHENYLETHYL CHLOROMETHYL KETONE
  • N-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
  • N-TOSYL-PHE-CHLOROMETHYLKETONE
  • N-TOSYLAMIDE PHENETHYL CHLOROMETHYLKETONE
  • P-TOLUENESULFONYL-L-PHENYLALANINE CHLOROMETHYL KETONE
  • N-ALPHA-TOSYL-PHE CHLOROMETHYL KETONE
  • N-ALPHA-P-TOSYL-L-PHENYLALANINE CHLOROMETHYIKETONE
  • (S)-1-CHLORO-3-TOSYLAMIDO-4-PHENYL-2-BUTANONE
  • (S)-1-CHLORO-4-PHENYL-3-TOSYLAMIDO-2-BUTANONE
  • TOS-PHE-CHLOROMETHYLKETONE
  • TOS-PHE-CMK
  • TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
  • TOSYL-L-PHENYLALANYL-CHLOROMETHANE
  • TPCK
  • (-)-p-toluenesulfonamid
  • l-1-tosylamido-2-phenylethylchloromethylketone
  • N-Tosyl-L-phenylalanine Chloromethyl Ketone(TPCK)
  • L-1-CHLORO-3-TOSYLAMIDO-4-PHENYL-2-BUTANONE RESEARCH GRADE
  • TPCK (N-TOSYL-L-PHENYLALANINE CHLOROMETH YL KETONE) \ PROTEASE INHIBITOR
  • N-p-Tosyl-L-phenylalanine chloromethyl ketone,(S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone, (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone, TPCK, Tosyl-L-phenylalanyl-chloromethane
  • N-(p-Toluenesulfonyl)-L-phenylalanyl ChloroMethyl Ketone
  • (S)-N-(4-Chloro-3-oxo-1-phenyl-2-butyl)-p-toluenesulfonamide N-Tosyl-L-phenylalanyl Chloromethyl Ketone TPCK
  • N-α-Tosyl-L-phenylalanylchloromethane
  • TPCK (Tosyl Phenylalanyl ChloroMethyl ketone
  • Chloro-3-tosylaMido-4-phenyl-2-butanone research grade
  • N- (p-toluenesulfonyl) -L- phenylalanyl chloride ketone (TPCK)
  • alpha-N-Tosyl-L-phenylalanine chloromethyl ketone
  • N-alpha-Tosyl-L-phenylalanylchloromethane
  • Tosylphenylalanylchloromethane
  • N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK)
  • N-(p-Toluenesulfonyl)-L-phenylalanine chloromethyl ketone
  • L-1-4'-Tosylamino-2-phenylethylechloromethyleketone
  • N-tosyl-L-phenylalanyl chloromethyl ketone
  • n-2-p-Tosyl-L-phenylalanine-chlorometjylketone
  • Tos-L-Phe-CMK
  • Tosyl-L-Phenylalanine chloromethylketone≥ 98% (TLC)
  • (S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide
  • (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone, (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone, Tosyl-L-phenylalanyl-chloromethane, TPCK
  • N-[(S)-α-(Chloroacetyl)phenethyl]-4-methylbenzenesulfonamide
  • N-p-Tosyl-L-phenylalanyl chloromethane
  • N-p-Tosyl-L-phenylalanyl chloromethyl ketone
  • Tos-L-Phe-Chloromethane
  • L-1-4'-Tosylamino-2-phenylethyl chloromethyl ketoneTPCK
  • l-n-(alpha-(chloroacetyl)phenethyl)-p-toluenesulfonamide
  • tosylphenylalanylchloromethylketone
  • L-chloromethyl (2-phenyl-1-(p-toluenesulphonylamino)ethyl) ketone
  • L-1-P-TOSYLAMINO-2-PHENYLETHYL CHLORO-METHYL KETONE, 99+%
  • L-1-4'-Tosylamino-2-phenylethyl chloromethyl ketone, 99+%
  • Chloro-3-tosylamido-4-phenyl-2-butanone
  • Benzenesulfonamide, N-(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl-4-methyl-
  • n-p-tosyl-l-phenylalanine chloromethyl ketone
  • L-1-4-Tosylamido-2-phenylethyl chloromethyl ketone.
  • L-1-PARA-TOSYLAMINO-2-PHENYLETHYLCHLOROMETHYLKETONE
  • L-1-TOSYLAMIDO-2-PHENYLETHYLCHLOROETHYLKETONE