P4265

Pepstatin A

Name: Pepstatin A
Brand: SIGMA

powder, ≥75% (HPLC)

Synonym(s):

Pepsin inhibitor

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₆₃N₅O₉

CAS Number:

26305-03-3

Molecular Weight:

685.89

NACRES:

NA.77

PubChem Substance ID:

24898519

UNSPSC Code:

12352202

EC Number:

247-600-0

MDL number:

MFCD00060740

Beilstein/REAXYS Number:

2201362

Product Name

Pepstatin A, microbial, ≥75% (HPLC)

InChI key

FAXGPCHRFPCXOO-LXTPJMTPSA-N

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

SMILES string

CC(C)C[C@H](NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CC(C)C)C(C)C)C(C)C)[C@@H](O)CC(O)=O

biological source

microbial

assay

≥75% (HPLC)

form

powder

mp

233 °C (dec.) (lit.)

solubility

ethanol: acetic acid (9:1): 1 mg/mL, clear to hazy, colorless

storage temp.

2-8°C

Quality Level

300

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Application

Can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes. For this application, the working concentration is typically between 1-10 μM.

Pepstatin A has been used:

as a component of synaptoneurosome buffer to homogenize the C57BL/6 striata
as a component of cyclin-dependent kinase 5 (Cdk5) lysis buffer
as an inhibitor to determine the chymotrypsin activity of California spiny lobster

Biochem/physiol Actions

Pepstatin A is an inhibitor of acid proteases (aspartyl peptidases). It forms a 1:1 complex with proteases such as pepsin, renin, cathepsin D, bovine chymosin, and protease B (Aspergillus niger). The inhibitor is highly selective and does not inhibit thiol proteases, neutral proteases, or serine proteases. Solubilized γ-secretase and retroviral protease are also inhibited by Pepstatin A. It has been used to characterize proteases from several sources.

Potent inhibitor of acid proteases, including pepsin, renin and cathepsin D and many microbial aspartic proteases. Effective concentration 1 μM. Stable for about 1 day.

Preparation Note

Pepstatin can be dissolved at 1 mg/ml in 10% (v/v) acetic acid in methanol (9:1 methanol:acetic acid). The inclusion of acetic acid may be necessary to dissolve this peptide in methanol or DMSO. It has been dissolved at 1 to 2 mg/ml in ethanol, but heat may be required for complete dissolution. Solutions of Pepstatin A can be heated as high as 60 °C without any decomposition of the peptide.
Stock solutions at 1 mg/ml are stable at least a week at 4 °C. A 1 mM solution in methanol or DMSO is stable for months at -20 °C. If solutions become darker yellow, the reagent is hydrolyzing.
A working concentration of 1 μM is stable for at least one day at room temperature.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000506029

0000443888

0000479052

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A chymotrypsin from the digestive tract of California spiny lobster, Panulirus interruptus: Purification and biochemical characterization

Bibo-Verdugo B, et al.

Marine Biotechnology, 17(4), 416-427 (2015)

Synaptoneurosome preparation from C57BL/6 striata

Puighermanal E, et al.

Bio-protocol, 6, e1735-e1735 (2016)

The mitotic exit network regulates the spatiotemporal activity of Cdc42 to maintain cell size.

Gabriel M Gihana et al.

The Journal of cell biology, 220(1) (2020-12-08)

During G1 in budding yeast, the Cdc42 GTPase establishes a polar front, along which actin is recruited to direct secretion for bud formation. Cdc42 localizes at the bud cortex and then redistributes between mother and daughter in anaphase. The molecular

Active Cdk5 Immunoprecipitation and Kinase Assay

Bankston AN, et al.

Bio-protocol, 7(13) (2017)

Cellular expression and antimicrobial function of a phylogenetically conserved novel histone 1x-like protein on mouse cells: a potential new class of pattern recognition receptor.

Evans, D.L., et al.

Journal of Neurochemistry, 86, 133-141 (2009)

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