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Pepstatin

CAS No.26305-03-3
Chemical Name:Pepstatin
CBNumber:CB5155004
Molecular Formula:C34H63N5O9
Formula Weight:685.89
MOL File:26305-03-3.mol

Pepstatin Property

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
biological source synthetic
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.
Specific Activity ≥100,000U/mg
BRN 2201362
Stability Stable. Incompatible with strong bases, strong acids.
InChIKey JKGWASGTXVCDML-LXTPJMTPSA-N
CAS DataBase Reference 26305-03-3(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII V6Y2T27Q1U
UNSPSC Code 51111800
NACRES NA.77

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P305+P351+P338

Pepstatin Price More Price(19)

Brand: Sigma-Aldrich(India)
Product number: P4265
Product name : Pepstatin A
Purity: microbial, ≥75% (HPLC)
Packaging: 1MG
Price: ₹4282.2
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: P5318
Product name : Pepstatin A
Purity: microbial, ≥90% (HPLC)
Packaging: 5MG
Price: ₹9136.3
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: P4265
Product name : Pepstatin A
Purity: microbial, ≥75% (HPLC)
Packaging: 5MG
Price: ₹9796.6
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: SAB4500553
Product name : Anti-CATD (light chain, Cleaved-Gly65) antibody produced in rabbit
Purity: affinity isolated antibody
Packaging: 100μG
Price: ₹50560.5
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: P4265
Product name : Pepstatin A
Purity: microbial, ≥75% (HPLC)
Packaging: 25MG
Price: ₹26986.4
Updated: 2022/06/14
Buy: 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 Antiviral;Aspartic proteases irreversible inhibitor
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.
Definition ChEBI: Pepstatin A is a pentapeptide isolated from Streptomyces testaceus. It is a potent inhibitor of aspartyl proteases. It has a role as a bacterial metabolite and an EC 3.4.23.* (aspartic endopeptidase) inhibitor. It is a pentapeptide and a secondary carboxamide. It is a conjugate acid of a pepstatin A(1-).
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
storage +4°C
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