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PEPS-RO

Roche

Pepstatin

from Streptomyces species

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Synonym(s):
Pepstatin A
Empirical Formula (Hill Notation):
C34H63N5O9
CAS Number:
Molecular Weight:
685.89
Enzyme Commission number:
Beilstein/REAXYS Number:
2201362
MDL number:
PubChem Substance ID:

biological source

synthetic

Quality Level

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

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1 of 4

This Item
P5318110175-MP2032
vibrant-m

PEPS-RO

Pepstatin

vibrant-m

P5318

Pepstatin A

vibrant-m

110175-M

Acetyl-Pepstatin

vibrant-m

P2032

Pepstatin A−Agarose

technique(s)

affinity chromatography: suitable, protein purification: suitable

technique(s)

-

technique(s)

-

technique(s)

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

ethanol: 1 mg/mL, acetic acid: soluble 300 μg/mL (6N), water: insoluble, methanol: 1 mg/mL, pyridine: soluble

solubility

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

solubility

50% acetic acid: 5 mg/mL

solubility

-

form

lyophilized

form

powder

form

solid

form

saline suspension

packaging

pkg of 10 mg (11359053001), pkg of 50 mg (11524488001), pkg of 2 mg (10253286001)

packaging

-

packaging

-

packaging

-

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

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.

Quality

Purity tested by HPLC.

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
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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


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