Pepstatin A

For research use only. Not for therapeutic Use.

  • CAT Number: I002902
  • CAS Number: 26305-03-3
  • Molecular Formula: C₃₄H₆₃N₅O₉
  • Molecular Weight: 685.89
  • Purity: ≥95%
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Pepstatin A(Cat No.:I002902)is a potent and specific inhibitor of aspartic proteases, such as pepsin, renin, and cathepsin D. It is a naturally occurring pentapeptide isolated from Streptomyces species and widely used in biochemical research to study protease activity and inhibition. By binding tightly to the active site of aspartic proteases, Pepstatin A prevents substrate cleavage, making it an essential tool in protease mechanism studies and drug discovery. Its role in investigating protease-related diseases, including cancer and neurodegenerative disorders, highlights its importance in pharmaceutical and enzymology research.


Catalog Number I002902
CAS Number 26305-03-3
Synonyms

Pepstatin; isovaleryl-DL-Val-DL-Val-Sta(3xi,4xi)-DL-Ala-Sta(3xi,4xi)-OH; 3-hydroxy-4-[2-[[3-hydroxy-6-methyl-4-[[3-methyl-2-[[3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoylamino]-6-methylheptanoic acid

Molecular Formula C₃₄H₆₃N₅O₉
Purity ≥95%
Target Metabolic Enzyme/Protease
Solubility DMSO: ≥ 25 mg/mL
Storage Store at -20°C
IUPAC Name (3S,4S)-3-hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid
InChI 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-,23-,24-,25-,26-,30-,31-/m0/s1
InChIKey FAXGPCHRFPCXOO-LXTPJMTPSA-N
SMILES C[C@@H](C(=O)N[C@@H](CC(C)C)[C@H](CC(=O)O)O)NC(=O)C[C@@H]([C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C)O
Reference

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[1]. Umezawa H, et al. Pepstatin, a new pepsin inhibitor produced by Actinomycetes. J Antibiot (Tokyo). 1970 May;23(5):259-62. <br />
[2]. Deiss LP, et al. Cathepsin D protease mediates programmed cell death induced by interferon-gamma, Fas/APO-1 and TNF-alpha. EMBO J. 1996 Aug 1;15(15):3861-70. <br />
[3]. Wu GS, et al. Potential role for cathepsin D in p53-dependent tumor suppression and chemosensitivity. Oncogene. 1998 Apr 30;16(17):2177-83. <br />
[4]. Athanassakis I, et al. Localization of pepstatin/’s inhibitory action during Fc-mediated antibody internalization: possible implications for antibody-mediated viral transmission. Cell Immunol. 2000 Feb 1;199(2):81-8.
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