A pentapeptide inhibitor of aspartic proteases
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Pepstatin A

Item No. 9000469

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-L-alaninamide
CAS Number
26305-03-3
Synonyms
  • NSC 272671
  • Pepsin Inhibitor S 735A
Molecular Formula
C34H63N5O9
Formula Weight
685.9
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3.3 mg/mlDMSO: 12.5 mg/ml
SMILES
CC(C)CC(N[C@@H](C(C)C)C(N[C@@H](C(C)C)C(N[C@@H](CC(C)C)[C@@H](O)CC(N[C@@H](C)C(N[C@@H](CC(C)C)[C@@H](O)CC(O)=O)=O)=O)=O)=O)=O
InChi Code
InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-
InChi Key
FAXGPCHRFPCXOO-LXTPJMTPSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Pepstatin A is a bacteria-derived pentapeptide inhibitor of aspartic proteases.1,2,3 It inhibits pepsin, cathepsin D, and HIV protease (IC50s = <0.005, <0.04, and 2 µM, respectively).2 Pepstatin A is also an inhibitor of renin (IC50s = 0.32 and 15 µM for the porcine and human enzymes, respectively).3 It inhibits HIV replication in infected H9 cells when used at a concentration of 100 µM and inhibits autophagy in PC12 cells.3,4 Pepstatin A (10 and 50 mg/kg) decreases gastric acid levels and completely prevents pylorus ulceration in pylorus-ligated rats.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Umezawa, H., Aoyagi, T., Morishima, H., et al. Pepstatin, a new pepsin inhibitor produced by actinomycetes. J. Antibiot. (Tokyo) 23(5), 259-262 (1970).

    2. Sarubbi, E., Seneci, P.F., Angelastro, M.R., et al. Peptide aldehydes as inhibitors of HIV protease. FEBS Lett. 319(3), 253-256 (1993).

    3. Eid, M., Evin, G., Castro, B., et al. New renin inhibitors homologous with pepstatin. Biochem. J. 197(2), 465-471 (1981).

    4. Isahara, K., Ohsawa, Y., Kanamori, S., et al. Regulation of a novel pathway for cell death by lysosomal aspartic and cysteine proteinases. Neuroscience 91(1), 233-249 (1999).

    Product Citations

    Nagakannan, P., Islam, M.I., Conrad, M., et al. Cathepsin B is an excutioner of ferroptosis. Biochim. Biophys. Acta Mol. Cell Res. 1868(3), 118928 (2021).