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T4376 Sigma-Aldrich

N-p-Tosyl-L-phenylalanine chloromethyl ketone

≥97% (TLC), powder

Synonym: (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone, (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone, TPCK, Tosyl-L-phenylalanyl-chloromethane

  • CAS Number 402-71-1

  • Empirical Formula (Hill Notation) C17H18ClNO3S

  • Molecular Weight 351.85

  •  Beilstein/REAXYS Number 2895215

  •  EC Number 206-954-6

  •  MDL number MFCD00000935

  •  PubChem Substance ID 24278737

  •  NACRES NA.77

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Properties

Related Categories A to C, Biochemicals and Reagents, Broad Spectrum Inhibitors of Proteolytic Enzyme Classes, Bromelain, Cell Biology,
Quality Level   200
biological source   synthetic
assay   ≥97% (TLC)
form   powder
potency   10-100 μM effective concentration
color   white
mp   106-108 °C (lit.)
solubility   DMSO: >10 mg/mL (stable for several months at 4°C.)
  ethanol: 20 mg/mL (stable for several months at 4°C. Stock solutions (10 mM in methanol or ethanol) are stable for several months at 4°C.)
storage temp.   −20°C
SMILES string   Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc2ccccc2)C(=O)CCl
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   MQUQNUAYKLCRME-INIZCTEOSA-N
Gene Information   human ... NFKB1(4790), NKAP(79576), NKRF(55922), NOS2(4843), PTGS2(5743)

Description

Application

N-p-Tosyl-L-phenylalanine chloromethyl ketone has been used:
• to investigate whether transcription factor NFκB is involved in renalase expression
• to test the role of NF-κB activation
• to study its inhibitory effect on chymotrypsin

Irreversible inhibitor of certain serine proteases; used to inhibit chymotrypsin in preparations of trypsin.

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).

N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK) blocks the lipopolysaccharide (LPS)- or cytokine-induced activation of nuclear factor κB (NFκB), which, in turn, blocks the induction of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (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). TPCK recognises the phenylalanine residue in chymotrypsin′s and prevents its function.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Caution

Shelf-life is at least two years when stored desiccated at -20 °C.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
UN 3335
WGK Germany 
WGK 3
RTECS 
XT5613500
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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