ACTH (4-7), prolyl-glycyl-proline-

Base Information

• Chemical Name: ACTH (4-7), prolyl-glycyl-proline-
• CAS No.: 80714-61-0
• Molecular Formula: C37H51N9O10S
• Molecular Weight: 813.932
• DSSTox Substance ID: DTXSID601001439
• Wikidata: Q4415058
• Mol file: 80714-61-0.mol

Synonyms:DTXSID601001439;Q4415058;L-Methionyl-L-alpha-glutamylhistidyl-L-phenylalanyl-L-prolylglycyl-L-proline;(2S)-1-[2-([(2S)-1-[(2S)-2-([2-([(2S)-2-([(2S)-2-amino-4-methylsulfanylbutanoyl]amino)-5-hydroxy-5-oxopentanoyl]amino)-3-(1H-imidazol-5-yl)propanoyl]amino)-3-phenylpropanoyl]pyrrolidine-2-carbonyl]amino)acetyl]pyrrolidine-2-carboxylic acid;N-{[1-(N-{2-[(2-{[2-Amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-carboxy-1-hydroxybutylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene}phenylalanyl)pyrrolidin-2-yl](hydroxy)methylidene}glycylproline

Chemical Property of ACTH (4-7), prolyl-glycyl-proline-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1335.2°Cat760mmHg
• PKA: 3.43±0.20(Predicted)
• Flash Point: 761.3°C
• PSA: 325.58000
• Density: 1.391g/cm³
• LogP: 2.71460
• Storage Temp.: ?20°C
• Solubility.: H2O: >2mg/mL
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 21
• Exact Mass: 813.34796003
• Heavy Atom Count: 57
• Complexity: 1450

Purity/Quality:

Semax ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSCCC(C(=O)NC(CCC(=O)O)C(=O)NC(CC1=CN=CN1)C(=O)NC(CC2=CC=CC=C2)C(=O)N3CCCC3C(=O)NCC(=O)N4CCCC4C(=O)O)N
• Isomeric SMILES: CSCC[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)NC(CC1=CN=CN1)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N3CCC[C@H]3C(=O)NCC(=O)N4CCC[C@H]4C(=O)O)N
• Description: Semax is a synthetic analogue of the adrenocorticotropic hormone, a hormone responsible for the production of cortisol which in turn regulates glucose and lipid metabolism and helps to maintain blood pressure. In the hippocampus, Semax rapidly elevates the levels of brain-derived neurotrophic factor (BDNF), a protein important in encouraging growth and differentiation of new neurons and synapses. BDNF is active in the hippocampus, cortex, and forebrain and is important for memory, coordination, concentration, and learning. Semax also works to activate the dopaminergic and serotonergic systems to help prime the brain for action and to induce a controlled state of mental stress.
• Clinical Use: Semax has undergone extensive study in Russia and is on the Russian List of Vital & Essential Drugs approved by the Russian Federation government on December 7, 2011. Medical uses for Semax include treatment of stroke, transient ischemic attack, memory and cognitive disorders, peptic ulcers, optic nerve disease, and to boost the immune system.

Technology Process of ACTH (4-7), prolyl-glycyl-proline-

There total 26 articles about ACTH (4-7), prolyl-glycyl-proline- 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: 88.0%

C50H75N9O12S (111491-74-8) → H-Met-Glu-His-Phe-Pro-Gly-Pro (80714-61-0)

Guidance literature:

With dimethylsulfide; trifluoroacetic acid; In various solvent(s); at 30 ℃; for 3h;

DOI:10.1007/BF00598358

Reference yield: 57.0%

Boc-Met-Glu-His-Phe-Pro-Gly-Pro (92411-06-8) → H-Met-Glu-His-Phe-Pro-Gly-Pro (80714-61-0)

Guidance literature:

With hydrogenchloride; In acetic acid; for 0.5h; Ambient temperature;

DOI:10.1007/BF00769795

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → H-Met-Glu-His-Phe-Pro-Gly-Pro (80714-61-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 53 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide, triethylamine / tetrahydrofuran / 48 h / Ambient temperature

2: 100 percent / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 70 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide, triethylamine / tetrahydrofuran / 48 h / Ambient temperature

4: CH₂Cl₂ / Ambient temperature

5: 75 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide, triethylamine / tetrahydrofuran / 48 h / Ambient temperature

6: CH₂Cl₂ / Ambient temperature

7: 1.) aq. H₂SO₄, 2.) 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide, triethylamine / 2.) THF, room temp., 3 days

8: 76 percent / 1,4-cyclohexadiene / Pd-black / ethanol / 2 h / Heating

9: 57 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature

With hydrogenchloride; cyclohexa-1,4-diene; sulfuric acid; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1007/BF00769795

upstream raw materials:

Boc-Met-Glu-His-Phe-Pro-Gly-Pro

C₅₀H₇₅N₉O₁₂S

1-(tert-butoxycarbonyl)-L-proline

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt

Downstream raw materials:

L-methionyl-L-glutamic acid

Refernces

• 1、 Krysin, E. P.,Karel'skii, V. N.,Rabinovich, A. K.,Borovkova, S. Yu.. "SYNTHESIS OF A HEPTAPEPTIDE FORMING A MODIFIED ACTH 4-10 FRAGMENT". . p. 706 - 709. Retrieved 2007/10/02.