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Pepstatin

Product Name
Pepstatin
CAS No.
26305-03-3
Chemical Name
Pepstatin
Synonyms
PEPSTATIN A;(3S,4S)-4-AMINO-3-HYDROXY-6-METHYL-HEPTANOIC ACID;CPSD;PEPSTATIN;PepstainA;ahpatininc;procidins735a;A Pepstatin A;Pepstatin A TFA;PEPSTATIN A 10MG
CBNumber
CB5155004
Molecular Formula
C34H63N5O9
Formula Weight
685.89
MOL File
26305-03-3.mol
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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
form 
White solid
pka
4.17±0.10(Predicted)
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)
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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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PEPS-RO
Product name
Pepstatin
Purity
from Streptomyces species
Packaging
2mg
Price
$103
Updated
2024/03/01
Sigma-Aldrich
Product number
PEPS-RO
Product name
Pepstatin
Purity
from Streptomyces species
Packaging
10mg
Price
$197
Updated
2024/03/01
Sigma-Aldrich
Product number
PEPS-RO
Product name
Pepstatin
Purity
from Streptomyces species
Packaging
50mg
Price
$472
Updated
2024/03/01
Sigma-Aldrich
Product number
516481-M
Product name
Pepstatin A, Synthetic - CAS 26305-03-3 - Calbiochem
Purity
Pepstatin A, Synthetic, CAS 26305-03-3, is a reversible inhibitor of aspartic proteases. Inhibits cathepsin D, pepsin, and renin.
Packaging
5mg
Price
$68.4
Updated
2024/03/01
Sigma-Aldrich
Product number
516481-M
Product name
Pepstatin A, Synthetic - CAS 26305-03-3 - Calbiochem
Purity
Pepstatin A, Synthetic, CAS 26305-03-3, is a reversible inhibitor of aspartic proteases. Inhibits cathepsin D, pepsin, and renin.
Packaging
25mg
Price
$207
Updated
2024/03/01
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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

Pepstatin Preparation Products And Raw materials

Raw materials

Preparation Products

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Pepstatin Suppliers

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View Lastest Price from Pepstatin manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Pepstatin 26305-03-3
Price
US $0.00-0.00/g
Min. Order
1g
Purity
98.0%
Supply Ability
1kg/month
Release date
2021-08-27
Apeloa production Co.,Limited
Product
Pepstatin 26305-03-3
Price
US $1.00/g
Min. Order
1g
Purity
0.98
Supply Ability
1000
Release date
2024-07-19
Hebei Weibang Biotechnology Co., Ltd
Product
Pepstatin 26305-03-3
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-25

26305-03-3, PepstatinRelated Search:

Kresoxim-methyl Basic Violet 1 Trypsin inhibitor CHLOROPHOSPHONAZO III Pepsin Methyl acrylate Methylparaben Leupeptin Aprotinin Methanol Acetonitrile Paraquat dichloride Methyl Saccharated Pepsin DL-4-Amino-3-hydroxybutyric acid (S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID ACETYL-PEPSTATIN,AC-PEPSTATIN,PEPSTATIN, ACETYL- PEPSTATIN A METHYL ESTER

  • ahpatininc
  • pepsininhibitors735a
  • procidins735a
  • PEPSTATIN
  • PEPSTATIN A
  • X-VAL-VAL-STATYL-ALA-STATIN
  • (3S,4S)-4-AMINO-3-HYDROXY-6-METHYL-HEPTANOIC ACID
  • AHMHA ISOVALERYL-L-VAL-L-VAL-AHMHA-L-ALA-STA
  • Pepstatin A, Ultra Pure
  • pepstatin|Pep A|PEP|peptistatin A|pepstatine A|Pepstatin A|pepstatine
  • pepstatin|Pepstatin A
  • Pepstatin A Microbial
  • N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-L-alaninamide
  • Anti-CATD (light chain, Cleaved-Gly65) antibody produced in rabbit
  • Cathepsin D heavy chain
  • Cathepsin D light chain
  • CPSD
  • Anti-CATD (heavy chain, Cleaved-Leu169) antibody produced in rabbit
  • EZNA KIT MICROELUTE VIRAL DNA/RNA
  • SUCROSE PROTEOMICS GRADE
  • A Pepstatin A
  • I-VALERYL-L-VAL-L-VAL-AHMHA-L-ALA-AHMHA
  • IVA-VAL-VAL-STA-ALA-STA
  • ISOVALERYL-VAL-VAL-4-AMINO-3-HYDROXY-6-METHYLHEPTANOYL-ALA-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID
  • ISOVALERYL-VAL-VAL-STA-ALA-STA
  • ISOVALERYL-VAL-VAL-STA-ALA-STA-OH
  • ISOVALERYL-VAL-VAL-STA-ALA-STA-OH (MICROBIAL PRODUCT)
  • ISOVALERYL-L-VAL-L-VAL-AHMHA-L-ALA-AHMHA STA
  • ISO-VALERYL-L-VAL-L-VAL-STA-L-ALA-STA
  • ISOVALERYL-L-VAL-L-VAL-STATINYL-L-ALA-STATINE
  • ISOVALERYL-L-VALYL-L-VALYL-[(3S,4S)-4-AMINO-3-HYDROXY-6-METHYLHEPTANOYL]-L-ALANYL[(3S,4S)-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID]
  • ISOVALERYL-L-VALYL-L-VALYL-4-AMINO-3-HYDROXY-6-METHYLHEPTANOYL-L-ALANYL-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID
  • ISOVAL-VAL-VAL-4-AMINO-3-HYDROXY-5-METHYLHEPTANOYL-ALA-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID
  • ISOVAL-VAL-VAL-STA-ALA-STA
  • Pepstatin (microbial product)
  • pepstatin A ~120'000 U/mg
  • pepstatin A from microbial source
  • PEPSTATIN A SYNTHETIC
  • PEPSTATIN ULTRA PURE GRADE
  • (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid
  • N-Isovaleryl-L-valyl-L-valyl-3-hydroxy-6-methyl-gamma-aminoheptanoyl-L-alanyl-3-hydroxy-6-methyl-gamma-aminoheptanoic acid
  • N-Isovaleryl-L-valyl-L-valyl-3-hydroxy-6-methyl-g-aminoheptanoyl-L-alanyl-3-hydroxy-6-methyl-g-aminoheptanoic acid
  • (3S,4S)-4-[N-[(3S,4S)-4-[N-[N-(3-Methyl-1-oxobutyl)-L-valyl]-L-valylamino]-3-hydroxy-6-methylheptanoyl]-L-alanylamino]-3-hydroxy-6-methylheptanoic acid
  • Isovalerylpepstatin
  • N-Isovaleryl-L-Val-L-Val-[(3S,4S)-3-hydroxy-4-amino*-6-methylheptanoyl]-L-Ala-[(3S,4S)-3-hydroxy-4-amino*-6-methylheptanoyl]-OH
  • L-Alaninamide, N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-(1S)-1-(1S)-2-carboxy-1-hydroxyethyl-3-methylbutyl-
  • PepstainA
  • Pepstatin, ≥98% (HPLC)
  • InSolution Pepstatin A, Synthetic - CAS 26305-03-3 - Calbiochem
  • Pepstatin A, Synthetic - CAS 26305-03-3 - Calbiochem
  • PEPSTATIN A 10MG
  • Pepstatin USP/EP/BP
  • 3-Trilinoleoylglycerol
  • (6S,9S,12S,13S,17S,20S,21S)-13,21-Dihydroxy-12,20-diisobutyl-6,9-diisopropyl-2,17-dimethyl-4,7,10,15,18-pentaoxo-5,8,11,16,19-pentaazatricosan-23-oic acid
  • Pepstatin A >95%
  • Pepstatin A TFA
  • 26305-03-3
  • 26175-03-3