(2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide

Base Information

• Chemical Name: (2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide
• CAS No.: 13434-13-4
• Molecular Formula: C₁₉H₃₅N₃O₅
• Molecular Weight: 385.504
• Nikkaji Number: J2.963.667B
• Wikipedia: Actinonin
• Mol file: 13434-13-4.mol

Synonyms:(-)-actinonin;SCHEMBL279122;(2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide;13434-13-4

Chemical Property of (2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 137-139°C
• Refractive Index: 1.513
• PKA: 9.19±0.20(Predicted)
• PSA: 118.97000
• Density: 1.14 g/cm³
• LogP: 1.92220
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 20 mg/ml).
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 385.25767123
• Heavy Atom Count: 27
• Complexity: 498

Purity/Quality:

98%,99%, ^*data from raw suppliers

Actinonin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(CC(=O)NO)C(=O)NC(C(C)C)C(=O)N1CCCC1CO
• Isomeric SMILES: CCCCC[C@@H](CC(=O)NO)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1CO
• Description: Actinonin (13434-13-4) is a potent hydroxamic acid inhibitor of aminopeptidases which displays analgesic effects by inhibiting enkephalin-degrading enzymes.1?Actinonin also inhibits peptide deformylase.2?Induces apoptosis and displays antitumor activity in vivo.3?Inhibits neutrophil collagenase and other MMPs.4 Induces mitochondrial proteotoxicity.5
• Uses: (-)-Actinonin is a bioactive peptide and antibiotic that is a potent inhibitor of aminopeptidase M and leucine aminopeptidase. Actinonin has observed to be an inhibitor of peptide deformylase, meprin A, and thermolysin. Actinonin also inhibits tumor cell invasion and matrix degradation along with displayed antitumor activity in vitro and in vivo as well as acting as an apoptotic inducer. Actinonin has been used as a control to inhibit meprin-β activity in C57BL/6 mice. It has also been used to study the high-affinity interaction of EcPDF with actinonin by 15N NMR spectroscopy and isothermal titration. A potent in vivo inhibitor of collagenase

Technology Process of (2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide

There total 28 articles about (2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide 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: 89.0%

(S,S,R)-(-)-Tribenzylactinonin → actinonin (149198-87-8,13434-13-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 26 ℃; for 4h; under 1520 Torr;

DOI:10.1039/P19930000459

Reference yield: 81.0%

tribenzyl-actinonin (122501-62-6,149198-86-7) → (S,S,R)-(-)-actinonin (13434-13-4,149198-87-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃; for 4h; under 1520 Torr;

DOI:10.1016/S0040-4039(00)82386-2

Reference yield: 80.0%

C33H47N3O5 (460754-33-0) → actinonin (149198-87-8,13434-13-4)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; at 20 ℃; for 3 - 5h; Concentration;

upstream raw materials:

t-Boc-L-valine

N-Boc-L-valine o-nitrophenyl ester

N-(N-Boc-L-valyl)-L-prolinol

(R)-(+)-2-(N-Benzyl-N-benzyloxycarbamoylmethyl)heptanoic acid

Downstream raw materials:

monoamyl succinic acid

(R)-(+)-2-pentylsuccinic acid

Refernces

• 1、 Inoue, Shin-Ichi,Nishioka, Hiromi,Abe, Hitoshi,Harayama, Takashi,Takeuchi, Yasuo. "Synthesis of (-)-actinonin". . p. 1705 - 1710. Retrieved 2011/07/30.
• 2、 -. "Asymmetric synthesis of (S,S,R)-(-)-actinonin and its analogs and uses therefor". . . Retrieved 2008/06/13.