Arginylphenylalanine

Base Information

• Chemical Name: Arginylphenylalanine
• CAS No.: 2047-13-4
• Molecular Formula: C15H23 N5 O3
• Molecular Weight: 321.379
• Hs Code.: 2925290090
• DSSTox Substance ID: DTXSID30942646
• Nikkaji Number: J80.373A
• Wikidata: Q27144134
• Metabolomics Workbench ID: 78689
• ChEMBL ID: CHEMBL92255
• Mol file: 2047-13-4.mol

Synonyms:arginylphenylalanine;L-Arg-L-Phe

Chemical Property of Arginylphenylalanine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 191.62000
• Density: 1.35 g/cm³
• LogP: 1.76210
• Storage Temp.: −20°C
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 321.18008961
• Heavy Atom Count: 23
• Complexity: 417

Purity/Quality:

98%Min ^*data from raw suppliers

H-Arg-Phe-OH acetate salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)C(CCCN=C(N)N)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)[C@H](CCCN=C(N)N)N

Technology Process of Arginylphenylalanine

There total 15 articles about Arginylphenylalanine 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:

N-(Nα-benzyloxycarbonyl-Nω-nitro-L-arginyl)-L-phenylalanine (106819-64-1) → L-arginyl-L-phenylalanine (2047-13-4,133410-92-1)

Guidance literature:

With methanol; palladium; Hydrogenation_.weiteres Reagens: Essigsaeure;

DOI:10.1021/ja01582a065

Reference yield:

N5-[imino(nitroamino)methyl]-N2-[(phenylmethoxy)carbonyl]-L-ornithine (2304-98-5) → L-arginyl-L-phenylalanine (2047-13-4,133410-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; THF / anschliessendes Behandeln mit L-Phenylalanin-aethylester-hydrochlorid und Triaethylamin in CHCl₃

2: aqueous acetone; aqueous NaOH

3: palladium; ethanol / Hydrogenation_.weiteres Reagens: Essigsaeure

With tetrahydrofuran; sodium hydroxide; ethanol; palladium; triethylamine; acetone;

Reference yield:

(Z)-Arg(NO2)-Phe-OMe (27169-20-6) → L-arginyl-L-phenylalanine (2047-13-4,133410-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; aqueous NaOH

2: palladium; ethanol / Hydrogenation_.weiteres Reagens: Essigsaeure

With methanol; sodium hydroxide; ethanol; palladium;

DOI:10.1021/ja01582a065

upstream raw materials:

N-(N^α-benzyloxycarbonyl-N^ω-nitro-L-arginyl)-L-phenylalanine

N-[N^ω-nitro-N^α-(4-nitro-benzyloxycarbonyl)-L-arginyl]-L-phenylalanine

N-(N^α,N^δ,N^ω-tris-benzyloxycarbonyl-L-arginyl)-L-phenylalanine benzyl ester

t-butyloxycarbonyl-L-arginine

Downstream raw materials:

Adpoc-L-Phe-D-Leu-L-Arg-L-Phe-NH₂

t-Bumeoc-L-Phe-D-Leu-L-Arg-L-Phe-NH₂

L-phenylalanine

Refernces

• 1、 Kino, Kuniki,Kotanaka, Yoichi,Arai, Toshinobu,Yagasaki, Makoto. "A novel L-amino acid ligase from Bacillus subtilis NBRC3134, a microorganism producing peptide-antibiotic rhizocticin". body text. p. 901 - 907. Retrieved 2009/11/30.
• 2、 Deddish, Peter A.,Jackman, Herbert L.,Skidgel, Randal A.,Erdoes, Ervin G.. "Differences in the hydrolysis of enkephalin congeners by the two domains of angiotensin converting enzyme". . p. 1459 - 1463. Retrieved 2007/10/03.