PEPS-RO

Roche

Pepstatin

Name: Pepstatin
Brand: ROCHE

from Streptomyces species

Synonym(s):

Pepstatin A

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₆₃N₅O₉

CAS Number:

26305-03-3

Molecular Weight:

685.89

EC Number:

3.4.14.9 (BRENDA, IUBMB)

PubChem Substance ID:

329820361

UNSPSC Code:

12352202

MDL number:

MFCD00060740

Beilstein/REAXYS Number:

2201362

NACRES:

NA.54

Form:

lyophilized

Biological source:

synthetic

Key Documents

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biological source

synthetic

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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This Item	110175-M	P2032	516481-M
Roche PEPS-RO Pepstatin	Millipore 110175-M Acetyl-Pepstatin	Sigma-Aldrich P2032 Pepstatin A−Agarose	Sigma-Aldrich 516481-M Pepstatin A, Synthetic
biological source synthetic	biological source -	biological source microbial (fermentation), plant	biological source -
technique(s) affinity chromatography: suitable, protein purification: suitable	technique(s) -	technique(s) affinity chromatography: suitable	technique(s) -
form lyophilized	form solid	form saline suspension	form solid
storage temp. 2-8°C	storage temp. −20°C	storage temp. 2-8°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 50% acetic acid: 5 mg/mL	solubility -	solubility DMSO: 1 mg/mL, methanol: 1 mg/mL
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).

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.

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.

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

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.

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.

Analysis Note

Purity tested by HPLC.

Other Notes

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

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Global Trade Item Number

SKU	GTIN
10253286001	04061838669872
11524488001	04061838703156
11359053001	04061838701299

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