Phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide

Base Information

• Chemical Name: Phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide
• CAS No.: 99566-27-5
• Molecular Formula: C₅₄H₇₆N₁₄O₁₀
• Molecular Weight: 1081.29
• Mol file: 99566-27-5.mol

Synonyms:F-8-F-amide;F-8-F-NH2;F8Famide;FF8 (morphine modulating peptide);FLFQPQRF-NH2;FMRFamide-like octapeptide;morphine modulating neuropeptide;neuropeptide FF;NPFF;octapeptide F8FA;Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2;phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide

Chemical Property of Phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide

Chemical Property:

• Refractive Index: 1.656
• PSA: 412.10000
• Density: 1.38 g/cm³
• LogP: 4.54270
• Storage Temp.: −20°C
• Water Solubility.: Soluble to 0.50 mg/ml in water.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 32
• Exact Mass: 1080.58688468
• Heavy Atom Count: 78
• Complexity: 2050

Purity/Quality:

98%Min ^*data from raw suppliers

Neuropeptide FF ^*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(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCC(=O)N)C(=O)N2CCCC2C(=O)NC(CCC(=O)N)C(=O)NC(CCCN=C(N)N)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)C(CC4=CC=CC=C4)N
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCC(=O)N)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)C(CC4=CC=CC=C4)N
• Description: Neuropeptide FF (NPFF) is a peptide expressed in the brain and spinal cord that shares a precursor protein with neuropeptide AF. NPFF is expressed primarily in the posterior pituitary, hypothalamus, and medulla. It is an agonist at NPFF1 and NPFF2 receptors (Kis = 2.82 and 0.21 nM, respectively, for human recombinant receptors) that inhibits forskolin-induced cAMP production in CHO cells (EC50s = 236 and 2.3 nM, respectively). NPFF activates parvocellular neurons in the paraventricular nucleus (PVN) of the hypothalamus to stimulate oxytocin release from their projections in the brain stem, thereby regulating baroreflex control of heart rate. However, it inhibits magnocellular PVN neurons by enhancing GABAergic input. It is also found in plasma and exogenous administration briefly increases mean arterial pressure (MAP) by 40 mm Hg in rats, an effect that is only partially blocked by the norepinephrine competitor guanethidine and the α1-adrenergic receptor antagonist prazosin . NPFF has anti-opioid effects in rodent models, inhibiting morphine-induced analgesia and inducing abstinence in morphine-tolerant rats. It also inhibits acquisition of conditioned place preference to cocaine in rats when administered at doses of 10 and 20 nmol.
• Uses: Endogenous antiopioid peptide and agonist at NPFF1 and NPFF2 receptors (Ki values are 2.82 and 0.21 nM respectively). Exhibits anorexigenic effects.

Technology Process of Phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide

There total 2 articles about Phenylalanyl-leucyl-phenylalanyl-glutaminyl-prolyl-glutaminyl-arginyl-phenylalaninamide 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:

Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine (71989-20-3) + Fmoc-L-Arg-OH (91000-69-0,130752-32-8) → neuropeptide FF (Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2) (99566-27-5)

Guidance literature:

N-Fmoc L-Phe; With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; solid phase reaction;

With N,N-dimethyl-formamide; solid phase reaction;

Fmoc-Leu-OH; Fmoc-Pro-OH; N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamine; Fmoc-L-Arg-OH; Further stages;

DOI:10.1016/j.peptides.2009.11.003

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + Boc-Gln-OH (13726-85-7) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + Boc-Arg(Tos)-OH (13836-37-8) → neuropeptide FF (Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-NH2) (99566-27-5)

Guidance literature:

Multistep reaction;

DOI:10.1021/jm00047a005

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

Boc-Gln-OH

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Arg(Tos)-OH

Refernces

• 1、 Gicquel,Mazarguil,Desprat,Allard,Devillers,Simonnet,Zajac. "Structure-activity study of neuropeptide FF: Contribution of N-terminal regions to affinity and activity". . p. 3477 - 3481. Retrieved 2007/10/02.