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Key Documents

P5318

Sigma-Aldrich

Pepstatin A

powder, ≥90% (HPLC)

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About This Item

Formula empirica (notazione di Hill):
C34H63N5O9
Numero CAS:
Peso molecolare:
685.89
Beilstein:
2201362
Numero CE:
Numero MDL:
Codice UNSPSC:
12352202
ID PubChem:
NACRES:
NA.77

product name

Pepstatin A, microbial, ≥90% (HPLC)

Origine biologica

microbial

Livello qualitativo

Saggio

≥90% (HPLC)

Forma fisica

powder

Punto di fusione

233 °C (dec.) (lit.)

Solubilità

ethanol: 1-2 mg/mL (with heat up to 60 °C)

Temperatura di conservazione

2-8°C

Stringa SMILE

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

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
FAXGPCHRFPCXOO-LXTPJMTPSA-N

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Descrizione generale

Pepstatin A is a naturally occurring chemotactic peptide and inhibitor of aspartic proteases that was initially isolated from culture filtrates of various Actinomycetes species, with the initial name simply of “pepstatin”. This name was later modified to “pepstatin A” to distinguish the original pepstatin from later derivatives. Pepstatin A notably contains the unusual amino acid 4-amino-hydroxy-6-methylheptanoic acid (AHMHA), which is known also as statine. The amino acid sequence of pepstatin A is N-Isovaleryl-L-Valyl-L-Valyl-AHMHA-L-Alanyl-AHMHA.

Applicazioni

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.

Azioni biochim/fisiol

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.

Nota sulla preparazione

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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