An inhibitor of chymotrypsin-like serine proteases
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Tosyl Phenylalanyl Chloromethyl Ketone

Item No. 20166

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-benzenesulfonamide
CAS Number
402-71-1
Synonyms
  • Nα-Tosyl-L-Phenylalanine Chloromethyl Ketone
  • TPCK
Molecular Formula
C17H18ClNO3S
Formula Weight
351.8
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 10 mg/ml
SMILES
CC1=CC=C(S(N[C@H](C(CCl)=O)CC2=CC=CC=C2)(=O)=O)C=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    100 mg

    $38

    Add

    250 mg

    $71

    Add

    500 mg

    $112

    Add

    1 g

    $168

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Tosyl phenylalanyl chloromethyl ketone (TPCK) is an irreversible inhibitor of chymotrypsin-like proteases that has been shown to affect cell proliferation, apoptosis, and tumorigenesis.1 It can disrupt PDK1 signaling to the AGC kinases, Akt, S6K1, and RSK, as well as MSK1 and MSK2.2 TPCK also inhibits superoxide production and suppresses neutrophil respiratory burst.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Blair, T.T., and Marini, M.A. A reexamination of the reaction of TPCK with α-chymotrypsin. FEBS Lett. 20(1), 41-43 (1972).

    2. Anjum, R., Pae, E., Blenis, J., et al. TPCK inhibits AGC kinases by direct activation loop adduction at phenylalanine-directed cysteine residues. FEBS Lett. 586(19), 3471-3476 (2012).

    3. Gillibert, M., Dehry, Z., Terrier, M., et al. Another biological effect of tosylphenylalanylchloromethane (TPCK): It prevents p47phox phosphorylation and translocation upon neutrophil stimulation. Biochem J. 386(Pt 3), 549-556 (2005).