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Pepstatin

Pepstatin structure

CAS No:
26305-03-3
Formula:
C34H63N5O9
Chemical Name:
Pepstatin
Synonyms:
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
Categories:
Biochemical Engineering > Enzymes and Coenzymes Drugs

Description

Pepstatin is a specific aspartic protease inhibitor produced by actinomycetes, with IC50s of 4.5 nM, 6.2 nM, 150 nM, 290 nM, 520 nM and 260 nM for hemoglobin-pepsin, hemoglobin-proctase, casein-pepsin, casein-proctase, casein-acid protease and hemoglobin-acid protease, respectively. Pepstatin Ammonium also inhibits HIV protease.

Pepstatin Basic Attributes

Molecular Weight：

685.89

Exact Mass：

685.462585

EC Number：

247-600-0

NSC Number：

272671

HScode：

29241990

Characteristics

PSA：

223.26000

XLogP3：

3.42170

Appearance：

solid

Density：

1.1±0.1 g/cm3

Melting Point：

233 °C (dec.)(lit.)

Boiling Point：

997.6°C at 760 mmHg

Flash Point：

557.1±34.3 °C

Refractive Index：

1.504

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.

Storage Conditions：

2-8°C

Vapor Pressure：

0mmHg at 25°C

Toxicity：

LD50 in mice, rats, rabbits, dogs (mg/kg): 1090, 875, 820, 450 i.p.; all >2000 orally (Umezawa, 1970)

Specific rotation：

D27 -90.3° (c = 0.288 in methanol)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

22-24/25

RTECS Number：

SC6155000

Stability/Shelf Life：

Stable. Incompatible with strong bases, strong acids.

Pepstatin Use and Manufacturing

Methods of Manufacturing

General procedure: 4.2 General procedure A: resin loading (0026) Solid phase peptide synthesis was conducted manually in a sinter-fitted polypropylene syringe. 2-Chlorotritylchloride (CTC) resin was preswelled in DCM (mL) for 15min and drained. The first amino acid in 0.4M DIPEA/DCM was added and the mixture was agitated for 3h. After draining the solvent, any free 2-CTC resin linkers were capped by treatment of the resin with a solution of 17:2:1 DCM/MeOH/DIPEA (3×3mL×5min), and subsequently with a solution of 8:1:1 DMF/DIPEA/acetic anhydride (2×3mL×10min). The resin was finally washed with DCM (2×3mL×1min), DMF (2×3mL×1min), DCM (2×3mL×1min) and DMF (2×3mL×1min). 4.3 General procedure B: Fmoc deprotection (0027) The resin was agitated with a solution of 10percent piperidine inDMF (2×3mL×3min) and subsequently washed with DMF(3×3mL×1min), DCM (3×3mL×1min), DMF (5×3mL×1min). The deprotected solutions were combined and diluted appropriately (100-fold for 0.05mmol resin loading). The resin loading was estimated by measuring the absorbance of the piperidine-fulvene adduct with 10percent piperidine in DMF as a reference (λ=301nm; ε=7800M

Uses

Can be used in conjunction with E64-d and Leupeptin A to inhibit the degradation of autophagic cargo inside autophagosomes. For this application, the working concentration is typically between 1-10 μM.

Computed Properties

Molecular Weight:685.9
XLogP3:3
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:22
Exact Mass:685.46257860
Monoisotopic Mass:685.46257860
Topological Polar Surface Area:223
Heavy Atom Count:48
Complexity:1060
Undefined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Pepstatin A

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Guide of Pepstatin

Description
Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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Pepstatin

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