L-Chlormethyl-(2-phenyl-1-(p-toluolsulfonylamino)ethyl)keton

Bezeichnung:L-Chlormethyl-(2-phenyl-1-(p-toluolsulfonylamino)ethyl)keton

CAS-Nr402-71-1

Englisch Name:TPCK

CBNumberCB0354828

SummenformelC17H18ClNO3S

Molgewicht351.85

MOL-Datei402-71-1.mol

Synonyma

L-Chlormethyl-(2-phenyl-1-(p-toluolsulfonylamino)ethyl)keton

L-Chlormethyl-(2-phenyl-1-(p-toluolsulfonylamino)ethyl)keton physikalisch-chemischer Eigenschaften

Schmelzpunkt	106-108 °C(lit.)
Siedepunkt	509.9±60.0 °C(Predicted)
Dichte	1.1350 (rough estimate)
Brechungsindex	1.6100 (estimate)
storage temp.	-20°C
Löslichkeit	DMSO: >10 mg/mL stable for several months at 4°C.
Aggregatzustand	powder
pka	8.71±0.50(Predicted)
Farbe	white
BRN	2895215
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
CAS Datenbank	402-71-1
EPA chemische Informationen	Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl- (402-71-1)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	37/38-41
S-Sätze:	26-36
RIDADR	UN 3335
WGK Germany	3
RTECS-Nr.	XT5613500
F	10-19-21
TSCA	Yes
HS Code	29350090

Gefahreninformationscode (GHS)

TPCK Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R37/38:Reizt die Atmungsorgane und die Haut.
R41:Gefahr ernster Augenschäden.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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
Chemische Eigenschaften
white crystalline powder
Verwenden
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).
Sicherheitsprofil
Experimental reproductive effects. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx, SOx, and Cl-.
Einzelnachweise
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

L-Chlormethyl-(2-phenyl-1-(p-toluolsulfonylamino)ethyl)keton Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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