Pepstatin

Product NamePepstatin

CAS26305-03-3

CBNumberCB5155004

MFC34H63N5O9

MW685.89

EINECS247-600-0

MDL NumberMFCD00060740

MOL File26305-03-3.mol

MSDS FileSDS

Chemical Properties

Melting point	233 °C (dec.)(lit.)
alpha	D27 -90.3° (c = 0.288 in methanol)
Boiling point	695.91°C (rough estimate)
Density	1.1340 (rough estimate)
refractive index	1.7500 (estimate)
storage temp.	2-8°C
solubility	10% acetic acid in methanol: 1 mg/mL
pka	4.17±0.10(Predicted)
form	White solid
color	Colorless needles
optical activity	Optical rotation: -90.0 ± 5° (c = 0.5, MeOH, 20°C).
Water Solubility	It is soluble in 10% (v/v) acetic acid in methanol (9:1 methanol:acetic acid) (1 mg/ml), ethanol (1-2 mg/ml with heat up to 60°C), DMSO (5 mg/ml), methanol (1 mg/ml), and acetic acid. Insoluble in benzene, chloroform, water, 1 M NaOH, and ether.
BRN	2201362
Stability	Stable. Incompatible with strong bases, strong acids.
InChIKey	JKGWASGTXVCDML-LXTPJMTPSA-N
CAS DataBase Reference	26305-03-3(CAS DataBase Reference)

Safety

Safety Statements	22-24/25
WGK Germany	2
RTECS	SC6155000
F	10
HS Code	29241990
Toxicity	LD50 in mice, rats, rabbits, dogs (mg/kg): 1090, 875, 820, 450 i.p.; all >2000 orally (Umezawa, 1970)

Pepstatin Price

Product number	Packaging	Price	Buy
Sigma-Aldrich PEPS-RO	2mg	$92.7	Buy
Sigma-Aldrich PEPS-RO	10mg	$178	Buy
Sigma-Aldrich SAB4500553	100μG	$450	Buy
Sigma-Aldrich PEPS-RO	50mg	$426	Buy
Sigma-Aldrich 516481-M	5mg	$61.4	Buy

Pepstatin Chemical Properties,Usage,Production

Description
Pepstatin A is a bacterial-derived chemotactic pentapeptide that irreversibly inhibits aspartic proteases, including pepsin, gastricsin, renin, cathepsin E, and cathepsin D. Pepstatin A has been reported to stimulate human neutrophil degranulation (EC₅₀ = 0.75 μM) and super oxide production (EC₅₀ = 1.5 μM). Pepstatin A has been widely used as a research tool in studies of protease mechanisms and biological functions and has been examined as a therapeutic agent for inflammatory conditions including gastric ulcer, edema, and hypertension.
Chemical Properties
solid
Uses
Pepstatin A are natural, statine-containing peptides that acts as inhibitor of aspartic protease enzymes.
Uses
As an aspartic proteases irreversible inhibitor, Pepstain A can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes.
Uses
Antiviral;Aspartic proteases irreversible inhibitor
General Description
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.
Biochem/physiol Actions
Primary Targetaspartic proteases
Safety Profile
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic fumes of NOx.
Enzyme inhibitor
This naturally occurring statine-containing peptidomimetic (FWfree-acid = 685.90 g/mol; CAS 26305-03-3), also called pepstatin A and isovalerylpepstatin and named systematically as N-(isovaleryl)-L-valyl-L-valyl-statylL-alanyl-statine (where the statyl residue is a (3S,4S)-4-amino-3-hydroxy-6- methylheptanoyl residue and the C-terminal statine is the corresponding acid), is a presumptive transition-state analogue for prototypical aspartate proteinase pepsin (Ki = 46 pM). Pepstatin will also inhibit other carboxy proteinases. The inhibitory effectiveness of statine-containing peptides has been widely exploited by incorporating the statine residue into peptides that otherwise match sequence preferences of the target enzyme’s sub-sites. Because pepstatin has a low solubility in water, it is often dissolved indimethyl sulfoxide, methanol, or ethanol. Note that many derivatives of pepstatin are available, each displaying a different spectrum of inhibitory effects. Pepstatin B and C are the N-(n-caproyl)- and N-(iso-caproyl)- derivatives, respectively. Note: Above a critical concentration of 0.1 mM in low ionic-strength and neutral buffers, pepstatin often polymerizes into filaments that be several micrometers in length and have characteristic diameters ranging between 6 and 12 nm
References
1) Merck Index 14:7147 2) Marciniszyn?et al.?(1976)?Mode of inhibition of acid proteases by pepstatin; J. Biol. Chem.,?251?7088 3) Oda (2012)?New families of carboxy peptidases: serine-carboxyl peptidases and glutamic peptidases; J. Biochem.,?151?13 4) Yoshida?et al. (2006)?Pepstatin A, an aspartic proteinase inhibitor, suppresses RANKL-induced osteoclast differentiation; J. Biochem.,?139?583

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