PEPS-RO

Pepstatina A

from Streptomyces species

• Sinónimos: Pepstatin A
• Fórmula empírica (notación de Hill): C₃₄H₆₃N₅O₉
• Número de CAS: 26305-03-3
• Peso molecular: 685.89
• Comisión internacional de enzimas: 3.4.14.9 (BRENDA, IUBMB)
• Beilstein/REAXYS Number: 2201362
• MDL number: MFCD00060740
• UNSPSC Code: 12352202
• PubChem Substance ID: 329820361

Propiedades

• biological source: synthetic
• Quality Level: 100
• form: lyophilized
• packaging: pkg of 10 mg (11359053001); pkg of 2 mg (10253286001); pkg of 50 mg (11524488001)
• manufacturer/tradename: Roche
• technique(s): affinity chromatography: suitable; protein purification: suitable
• mp: 233 °C (dec.) (lit.)
• solubility: ethanol: 1 mg/mL; methanol: 1 mg/mL; acetic acid: soluble 300 μg/mL (6N); pyridine: soluble; water: insoluble
• storage temp.: 2-8°C
• 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
• 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
• InChI key: FAXGPCHRFPCXOO-LXTPJMTPSA-N

Descripción

General description

Isovaleryl-L-val-L-val-statyl-L-alanyl-statin (Isovaleryl-L-val-L-val-4-(S)-amino-3-(S)-hydroxy-6-methyl-heptanoyl-2-ala-4-(S)-amino-3-(S)-hydroxy-6-methyl-heptanoic acid)
Pepstatin is a low molecular weight, highly specific inhibitor of acid proteases (in particular aspartate proteases).

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.

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

La pepstatina A es un inhibidor de las proteasas ácidas (aspartil peptidasas). Forma un complejo 1:1 con proteasas como la pepsina, la renina, la catepsina D, la quimosina bovina y la proteasa B (Aspergillus niger). El inhibidor es muy selectivo y no inhibe las tiol proteasas, las proteasas neutras ni las serín-proteasas. La γ-secretasa solubilizada y la proteasa retroviral son también inhibidas por la pepstatina A. Se ha utilizado para caracterizar proteasas de diversas procedencias.

Quality

Purity tested by HPLC.

Preparation Note

La pepstatina puede disolverse a 1 mg/ml en ácido acético al 10 % (v/v) en metanol (9:1 metanol:ácido acético). Puede ser necesario añadir ácido acético para disolver este péptido en metanol o DMSO. Se ha disuelto a 1 - 2 mg/ml en etanol, pero puede requerirse calor para la disolución completa. Las disoluciones de pepstatina A pueden calentarse hasta 60 °C sin que se descomponga el péptido.
Las disoluciones de reserva a 1 mg/ml son estables por lo menos durante una semana a 4 °C. Una disolución 1 mM en metanol o DMSO es estable durante meses a -20 °C. Si las disoluciones se vuelven de color amarillo oscuros, el reactivo se está hidrolizando.
Una concentración de trabajo de 1 μM es estable durante como mínimo un día a temperatura ambiente.

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

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.

Other Notes

For life science research only. Not for use in diagnostic procedures.

Información de seguridad

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable