Pepstatin

Pepstatin
Other names	Pepstatin A
Identifiers
CAS number	26305-03-3
PubChem	5478883
SMILES	CC(C)CC(C(CC(=O)O)O)NC(=O)C(C)NC(=O) CC(C(CC(C)C)NC(=O)C(C(C)C)NC(=O) C(C(C)C)NC(=O)CC(C)C)O
Properties
Molecular formula	C34H63N5O9
Molar mass	685.892
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pepstatin is a potent inhibitor of aspartyl proteases. It is a hexa-peptide containing the unusual amino acid statine (Sta, (3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid), having the sequence Iva-Val-Val-Sta-Ala-Sta. It was originally isolated from cultures of various species of Actinomyces^[1] due to its ability to inhibit pepsin at picomolar concentrations^[2]. It was later found to inhibit nearly all acid proteases with high potency and, as such, has become a valuable research tool, as well as a common constituent of protease inhibitor cocktails.

Pepstatin is practically insoluble in water, chloroform, ether, and benzene, however it can be dissolved in methanol, ethanol and DMSO with acetic acid^[3], to between 1 and 5 mg/ml.

References

1. ^ Umezawa H, Aoyagi T, Morishima H, Matsuzaki M, Hamada M (1970). "Pepstatin, a new pepsin inhibitor produced by Actinomycetes". J. Antibiot. 23 (5): 259–62. PMID 4912600. 
2. ^ Marciniszyn J, Hartsuck JA, Tang J (1976). "Mode of inhibition of acid proteases by pepstatin". J. Biol. Chem. 251 (22): 7088–94. PMID 993206. 
3. ^ The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals (14th Edition - Version 14.4), Monograph 07147, ISBN 978-1-60119-491-6

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