Pepstatin

Base Information

• Chemical Name: Pepstatin
• CAS No.: 26305-03-3
• Deprecated CAS: 26368-29-6
• Molecular Formula: C34H63N5O9
• Molecular Weight: 685.902
• Hs Code.: 29241990
• European Community (EC) Number: 247-600-0
• UNII: V6Y2T27Q1U
• DSSTox Substance ID: DTXSID7046095
• Nikkaji Number: J17.063A
• Wikipedia: Pepstatin
• Wikidata: Q7166509
• NCI Thesaurus Code: C96295
• Pharos Ligand ID: 9JCCA64K6LWK
• Metabolomics Workbench ID: 144334
• ChEMBL ID: CHEMBL296588
• Mol file: 26305-03-3.mol

Synonyms:ahpatinin C;pepstatin;pepstatin A

Chemical Property of Pepstatin

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 233 °C (dec.)(lit.)
• Refractive Index: 1.7500 (estimate)
• Boiling Point: 997.57 °C at 760 mmHg
• Flash Point: 557.111 °C
• PSA: 223.26000
• Density: 1.118 g/cm³
• LogP: 3.42170
• XLogP3: 3
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 22
• Exact Mass: 685.46257860
• Heavy Atom Count: 48
• Complexity: 1060

Purity/Quality:

Pepstatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(CC(=O)O)O)NC(=O)C(C)NC(=O)CC(C(CC(C)C)NC(=O)C(C(C)C)NC(=O)C(C(C)C)NC(=O)CC(C)C)O
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC(C)C)[C@H](CC(=O)O)O)NC(=O)C[C@@H]([C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C)O
• 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.
• Uses: Antiviral;Aspartic proteases irreversible inhibitor 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. Pepstatin A are natural, statine-containing peptides that acts as inhibitor of aspartic protease enzymes.

Technology Process of Pepstatin

There total 2 articles about Pepstatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

3-methylbutyric acid (503-74-2) + Fmoc-Val-OH (68858-20-8) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + (3S,4S)-(9-fluorenylmethoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid (158257-40-0) → pepstatin A (26305-03-3)

Guidance literature:

(3S,4S)-(9-fluorenylmethoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h;

With piperidine; In N,N-dimethyl-formamide; for 0.1h;

3-methylbutyric acid; Fmoc-Val-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (3S,4S)-(9-fluorenylmethoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid; Further stages;

DOI:10.1016/j.tet.2017.12.033

Reference yield:

→ acetyl pepstatin (26305-03-3)

Guidance literature:

synth. hergestellt;

Reference yield: 90.0%

N-BOC-1,2-diaminoethane (57260-73-8) + pepstatin A (26305-03-3) → C36H69N7O8

Guidance literature:

N-BOC-1,2-diaminoethane; pepstatin A; With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

With trifluoroacetic acid; at 20 ℃; for 1h;

upstream raw materials:

3-methylbutyric acid

Fmoc-Val-OH

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

(3S,4S)-(9-fluorenylmethoxycarbonyl)-4-amino-3-hydroxy-6-methylheptanoic acid

Downstream raw materials:

N-(3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)propylcarbonyl)-N'-(pepstatinyl)propane-1,3-diamine

N-(t-butyloxycarbonyl)-N'-(pepstatinyl)propane-1,3-diamine

N-(pepstatinyl)propane-1,3-diamine

Refernces