Pepstatin

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ImageFile=Pepstatin.pngImageSize=300px
IUPACName=
OtherNames=Pepstatin A
Section1= Chembox Identifiers
CASNo=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
Section2= Chembox Properties
Formula=C₃₄H₆₃N₅O₉
MolarMass=685.892
Appearance=
Density=
MeltingPt=
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Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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 Actinomycescite journal |author=Umezawa H, Aoyagi T, Morishima H, Matsuzaki M, Hamada M |title=Pepstatin, a new pepsin inhibitor produced by Actinomycetes |journal=J. Antibiot. |volume=23 |issue=5 |pages=259–62 |year=1970 |pmid=4912600 |doi=] due to its ability to inhibit pepsin at picomolar concentrationscite journal |author=Marciniszyn J, Hartsuck JA, Tang J |title=Mode of inhibition of acid proteases by pepstatin |journal=J. Biol. Chem. |volume=251 |issue=22 |pages=7088–94 |year=1976 |pmid=993206 |doi=] . 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 insoluble at any concentration in methanol or DMSO, it is also sparingly soluble in water. It can, however, be dissolved at 1mg/ml 10% acetic acid in methanol.

References