Pepstatin
ROCHE/PEPS-RO - from Streptomyces species
Synonym: Pepstatin A
CAS Number: 26305-03-3
Empirical Formula (Hill Notation): C34H63N5O9
Molecular Weight: 685.89
MDL Number: MFCD00060740
Linear Formula: C34H63N5O9
Product Type: Chemical
| biological source | synthetic |
| form | lyophilized |
| InChI | 1S/C34H63N5O9/c1-17(2)12- |
| InChI key | FAXGPCHRFPCXOO-LXTPJMTPSA |
| manufacturer/tradename | Roche |
| mp | 233 °C (dec.) (lit.) |
| packaging | pkg of 10 mg (11359053001) |
| pkg of 2 mg (10253286001) | |
| pkg of 50 mg (11524488001) | |
| Quality Level | 100  |
| SMILES string | CC(C)C[C@H](NC(=O)[C@H](C |
| solubility | acetic acid: soluble 300 μg/mL (6N) |
| ethanol: 1 mg/mL | |
| methanol: 1 mg/mL | |
| pyridine: soluble | |
| water: insoluble | |
| storage temp. | 2-8°C |
| technique(s) | affinity chromatography: suitable |
| protein purification: suitable |
| Application: | Pepstatin is used for the protection of proteins and enzymes during isolation and purification procedures. It facilitates the investigation of enzyme mechanisms and biological function, and the classification of proteases. Pepstatin is applied in affinity chromatography, structural and pharmacological research, in HIV research (inhibition of retroviral-coded proteases, e.g., HIV-1), and cancer research (as an immunostimulant and anti-tumor drug). |
| 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. |
| General description: | Isovaleryl-L-val-L-val-st Pepstatin is a low molecular weight, highly specific inhibitor of acid proteases (in particular aspartate proteases). |
| Other Notes: | For life science research only. Not for use in diagnostic procedures. |
| Preparation Note: | Working concentration: 0.7 μg/ml (1 μM) Working solution: Recommended solvent is methanol (1 mg/ml), ethanol, DMSO or glacial acetic acid. Pepstatin is insoluble in pure water, but it is possible to produce an aqueous solutions with methanol (1.5–2.0 mg/ml), ethanol (1 mg/ml if allowed to sit overnight) or DMSO. Pepstatin is also soluble in acetic acid (6 N, 300 μg/ml) and pyridine. Solubility in NaCl solution is not known. Sodium or magnesium salts of pepstatin are water-soluble. Stock solution: 1.4 mg pepstatin/mI (2 mM), in methanol Storage conditions (working solution): -15 to -25 °C |
| 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. |
| Quality: | Purity tested by HPLC. |
| Reconstitution: | Soluble in methanol to approximately 1 mg/ml. Also soluble to 1 mg/ml in ethanol if allowed to sit overnight, and to 300 μg/ml in 6 N acetic acid. Stable for at least one week at 2 to 8 °C, or one month when stored in aliquots at -15 to -25 °C. |
| Specificity: | Pepstatin potently inhibits the HIV protease and other aspartic proteases, such as pepsin, renin, cathepsin D, chymosin, protease B from Aspergillus niger, and acid proteases of microbial origin. |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 1 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| mp | 233 °C (dec.) (lit.) |
| Storage Temp. | 2-8°C |
| Enzyme Commission (EC) Number | 3.4.14.9 ( BRENDA  | IUBMB ) |
| UNSPSC | 12352200 |