2-[[2-[[2-[[2-[[2-[2-[[2-[[6-Amino-2-[[4-amino-2-[[2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]acetyl]amino]propanoylamino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoic acid

Base Information

• Chemical Name: 2-[[2-[[2-[[2-[[2-[2-[[2-[[6-Amino-2-[[4-amino-2-[[2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]acetyl]amino]propanoylamino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoic acid
• CAS No.: 131602-53-4
• Molecular Formula: C₄₅H₈₁N₁₃O₁₄S
• Molecular Weight: 1060.28
• Hs Code.: 2930909899
• DSSTox Substance ID: DTXSID80392197
• Mol file: 131602-53-4.mol

Synonyms:Abeta25-35;ABP,25-35;amyloid beta-protein (25-35);beta-amyloid (25-35);beta-amyloid 25-35 peptide

Chemical Property of 2-[[2-[[2-[[2-[[2-[2-[[2-[[6-Amino-2-[[4-amino-2-[[2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]acetyl]amino]propanoylamino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.544
• Boiling Point: 1517.336°C at 760 mmHg
• PKA: 3.24±0.10(Predicted)
• Flash Point: 871.453°C
• PSA: 468.96000
• Density: 1.249g/cm³
• LogP: 1.05840
• Storage Temp.: −20°C
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥106 mg/mL in DMSO
• Water Solubility.: Soluble in water.
• XLogP3: -4.9
• Hydrogen Bond Donor Count: 15
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 37
• Exact Mass: 1059.57466548
• Heavy Atom Count: 73
• Complexity: 1880

Purity/Quality:

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

β-Amyloid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)NC(C(C)CC)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(CCSC)C(=O)O)NC(=O)C(C)NC(=O)CNC(=O)C(CCCCN)NC(=O)C(CC(=O)N)NC(=O)C(CO)NC(=O)CN
• Description: Beta-amyloid protein (Abeta), a major component of senile plaques of Alzheimer's disease (AD) in the brain, causes elevation of the intracellular free Ca2+ level and the production of robust free radicals. Beta-amyloid 25-35 induced apoptosis, characterized by decreased cell viability, neuronal DNA condensation, and fragmentation, is associated with an increase in intracellular free Ca2+ level, the accumulation of reactive oxygen species (ROS), and the activation of caspase-3. All of these effects induced by beta-amyloid 25-35 are reversed by genistein.
• Uses: Amyloid β-Protein Fragment 25-35 has been used:to induce neurotoxicity in cortical culturesto induce Alzheimer′s disease in rat modelto induce apoptosis in mesenchymal stem cells (MSCs)

Technology Process of 2-[[2-[[2-[[2-[[2-[2-[[2-[[6-Amino-2-[[4-amino-2-[[2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]acetyl]amino]propanoylamino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoic acid

There total 3 articles about 2-[[2-[[2-[[2-[[2-[2-[[2-[[6-Amino-2-[[4-amino-2-[[2-[(2-aminoacetyl)amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]acetyl]amino]propanoylamino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-4-methylsulfanylbutanoic acid 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: 11.0%

Fmoc-Met-Wang resin + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Ile-OH (71989-23-6,251316-98-0) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → amyloid β-protein fragment 25-35 (131602-53-4)

Guidance literature:

Fmoc-Met-Wang resin; With piperidine; In N,N-dimethyl-formamide; for 0.1h; 2-Chlorotrityl resin

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; Enzymatic reaction;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Ser(tBu)-OH; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-Asn-OH-PG;

DOI:10.1016/j.bmcl.2015.05.029

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + Fmoc-Ile-OH (71989-23-6,251316-98-0) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine (71989-28-1) + Fmoc-Asn-OH (71989-16-7) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → amyloid β-protein fragment 25-35 (131602-53-4)

Guidance literature:

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; With 17α-acetoxy-6-formyl-3-methoxypregna-3,5-dien-20-one; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20 - 65 ℃; for 0.333333h; Microwave irradiation;

With piperazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-Asn-OH; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; Further stages;

DOI:10.1039/c5ra23441g

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Ile-OH (71989-23-6,251316-98-0) + Fmoc-Lys-OH (105047-45-8) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → amyloid β-protein fragment 25-35 (131602-53-4)

Guidance literature:

Multistep reaction;

DOI:10.1021/jm040773o

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Ile-OH

Fmoc-Lys-OH

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Refernces

• 1、 Shinoda, Kiyomichi,Sohma, Youhei,Kanai, Motomu. "Synthesis of chemically-tethered amyloid-β segment trimer possessing amyloidogenic properties". supporting information. p. 2976 - 2979. Retrieved 2015/06/22.