Boc-Met-Leu-Phe-OH

Base Information

• Chemical Name: Boc-Met-Leu-Phe-OH
• CAS No.: 67247-12-5
• Molecular Formula: C25H39 N3 O6 S
• Molecular Weight: 509.667
• ChEMBL ID: CHEMBL1770296
• Nikkaji Number: J482.683C
• Mol file: 67247-12-5.mol

Synonyms:BOC-Met-Leu-Phe;Boc1 peptide;N-t-butoxycarbonyl-methionyl-leucyl-phenylalanine;t-boc-MLP;t-butyloxycarbonyl-1-methionyl-1-leucyl-1-phenylatanine;t-butyloxycarbonyl-methionyl-leucyl-phenylalanine

Chemical Property of Boc-Met-Leu-Phe-OH

Chemical Property:

• Vapor Pressure: 2.28E-24mmHg at 25°C
• Boiling Point: 761.3°Cat760mmHg
• Flash Point: 414.2°C
• PSA: 159.13000
• Density: 1.165g/cm³
• LogP: 4.14850
• Storage Temp.: -15°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 509.25595715
• Heavy Atom Count: 35
• Complexity: 704

Purity/Quality:

99%+, ^*data from raw suppliers

Boc-Met-Leu-Phe-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)O)NC(=O)C(CCSC)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)NC(=O)[C@H](CCSC)NC(=O)OC(C)(C)C
• Uses: Chemotactic peptide antagonist. Boc-MLF is an antagonist that preferentially inhibit activity triggered through the formyl peptide receptor.

Technology Process of Boc-Met-Leu-Phe-OH

There total 10 articles about Boc-Met-Leu-Phe-OH 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%

N-tert-butoxycarbonyl-L-methionine (2488-15-5) + Leu-Phe-OH (3063-05-6) → tert-butyloxycarbonyl-methionyl-leucyl-phenylalanine (67247-12-5)

Guidance literature:

With benzyltrimethylammonium chloride; In chloroform; for 3h; Ambient temperature;

DOI:10.1039/c39900001045

Reference yield: 80.0%

Boc-Met-Leu-Phe-OMe (77542-78-0) → tert-butyloxycarbonyl-methionyl-leucyl-phenylalanine (67247-12-5)

Guidance literature:

With phosphate buffer; In tert-butyl alcohol; at 35 ℃; alcalase;

DOI:10.1080/00397919208055416

Reference yield:

(2S)-2-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)-4-methylpentanoic acid (33014-87-8) → tert-butyloxycarbonyl-methionyl-leucyl-phenylalanine (67247-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC; Et₃N

2: alcalase; H₂O / acetone / pH 8.2

With Alcalase; water; triethylamine; dicyclohexyl-carbodiimide; In acetone; 1: Condensation / 2: Hydrolysis;

DOI:10.1002/jccs.199900046

upstream raw materials:

N-tert-butoxycarbonyl-L-methionine

Leu-Phe-OH

(2S)-2-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)-4-methylpentanoic acid

Phenylalanine benzyltrimethylammonium salt

Downstream raw materials:

formyl-methionyl-leucyl-phenylalanine

Refernces

• 1、 Chen,Hsiao,Chang,Wang. "Chemo-enzymatic synthesis of Fmoc-peptide fragments". . p. 391 - 398. Retrieved 2007/10/02.
• 2、 Chen,Wang. "Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences". . p. 1045 - 1047. Retrieved 2007/10/02.