Fmrfamide

Base Information

• Chemical Name: Fmrfamide
• CAS No.: 64190-70-1
• Molecular Formula: C29H42 N8 O4 S
• Molecular Weight: 598.77
• UNII: 8953X1KZFL
• Nikkaji Number: J353.957A
• Wikipedia: FMRFamide
• Wikidata: Q5426656
• ChEMBL ID: CHEMBL262202
• Mol file: 64190-70-1.mol

Synonyms:FMRF;FMRF amide;FMRF NH2;FMRF-amide;FMRF-NH2;FMRFamide;FMRFamide, (D-Arg)-Isomer;FMRFamide, (D-Met)-Isomer;FMRFamide, (D-Phe)-Isomer;FMRFamide, (D-phenylalanine)-Isomer;Phe Met Arg Phe amide;Phe-Met-Arg-Phe-amide;Phe-Met-Arg-Phe-NH2

Chemical Property of Fmrfamide

Chemical Property:

• PKA: 13.35±0.46(Predicted)
• PSA: 243.61000
• Density: 1.32 g/cm³
• LogP: 3.51940
• Storage Temp.: −20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 18
• Exact Mass: 598.30497302
• Heavy Atom Count: 42
• Complexity: 889

Purity/Quality:

99% ^*data from raw suppliers

FMRF amide ^*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: CSCCC(C(=O)NC(CCCN=C(N)N)C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)C(CC2=CC=CC=C2)N
• Isomeric SMILES: CSCC[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N)NC(=O)[C@H](CC2=CC=CC=C2)N
• Description: FMRFamide (FMRFa) was originally isolated as a cardioacceleratory peptide from mollusks. To date, a number of biologically active FMRFas and their related peptides have been identified.
• Biological functions: Target cells and function The predominant effect of FaRPs is the reduction of spontaneous muscle contractions, such as in the intestinal muscle and the heart rate. Among FaRP subtypes, some FaRPs function in gut contraction and other subtypes do not.?Physiological discrimination according to different?subtype of FaRPs results in extensive functions.For example, FaRPs exert acceleratory effects on the heart rate, inhibitory effects on gut motility, and modulate synaptic activity. Furthermore, sequential ecdysis behavior is also regulated by FaRPs, consequently activating the downstream of the eclosion hormone (EH) and ecdysistriggering hormone (ETH).During ecdysis, FaRP-expressing Tv neurons are activated by ETH.

Technology Process of Fmrfamide

There total 14 articles about Fmrfamide 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: 82.0%

L-Phenylalanine amide (5241-58-7) + H-Phe-Met-Arg-OH (123197-18-2) → Neuropeptide C (64190-70-1,84313-42-8,84413-35-4,84313-44-0)

Guidance literature:

With thermolysin; In methanol; for 3h; Product distribution; Ambient temperature; effect of the pH, conc. of MeOH, reaction time;

DOI:10.1248/cpb.36.4345

Reference yield: 67.0%

Boc-Phe-Met-Arg(Mts)-Phe-NH2 (123197-28-4) → Neuropeptide C (64190-70-1,84313-42-8,84413-35-4,84313-44-0)

Guidance literature:

With ethandithiol; trifluorormethanesulfonic acid; methyl-phenyl-thioether; In trifluoroacetic acid; for 1h;

DOI:10.1248/cpb.36.4345

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Neuropeptide C (64190-70-1,84313-42-8,84413-35-4,84313-44-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / N-methylmorpholine / dimethylformamide; tetrahydrofuran / 3 h

2: 89 percent / N-methylmorpholine, HOBt, DCC / dimethylformamide / 16 h

3: 67 percent / TFMSA-thioanisole, ethanedithiol / trifluoroacetic acid / 1 h

With 4-methyl-morpholine; ethandithiol; trifluorormethanesulfonic acid; methyl-phenyl-thioether; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1248/cpb.36.4345

upstream raw materials:

L-Phenylalanine amide

H-Phe-Met-Arg-OH

Boc-Phe-Met-Arg(Mts)-Phe-NH₂

N-benzoxycarbonyl-L-phenylalanyl-L-methionyl-N-^γ-nitro-L-arginyl-L-phenylalaninamide

Refernces

• 1、 Sakina,Kawazura,Morihara,Yajima. "Thermolysin-catalyzed synthesis of peptide amides". . p. 4345 - 4354. Retrieved 2007/10/02.