N-Formylmethionyl-leucylphenylalanine

Base Information

• Chemical Name: N-Formylmethionyl-leucylphenylalanine
• CAS No.: 59880-97-6
• Molecular Formula: C21H31 N3 O5 S
• Molecular Weight: 437.56
• Hs Code.: 2922299090
• NSC Number: 350593
• Wikidata: Q27190628
• Mol file: 59880-97-6.mol

Synonyms:N-FORMYLMETHIONYL-LEUCYLPHENYLALANINE;2-[[2-[(2-formamido-4-methylsulfanylbutanoyl)amino]-4-methylpentanoyl]amino]-3-phenylpropanoic acid;fMLP;N-Formyl-MLF;LO6AVJ8RCE;Formyl-Met-Leu-Phe-OH;N-formylmethionylleucylphenylalanine;C21H31N3O5S;C21-H31-N3-O5-S;NSC-350593;UNII-LO6AVJ8RCE;Spectrum2_000008;Spectrum3_001520;Spectrum4_001047;Spectrum5_000682;SCHEMBL39528;BSPBio_003199;KBioGR_001314;DivK1c_000587;SPECTRUM1502173;SPBio_000015;HMS501N09;KBio1_000587;KBio3_002699;CHEBI:111167;NINDS_000587;HMS3373L20;HMS3746O15;CCG-40032;NSC350593;AKOS024287990;NSC 350593;IDI1_000587;NCGC00096001-01;NCGC00096001-02;FT-0640642;BRD-A27693633-001-02-9;Q27190628;L-Phenylalanine, N-(N-(N-formyl-L-methionyl)-L-leucyl)-;2-[[2-[[2-formamido-4-(methylthio)-1-oxobutyl]amino]-4-methyl-1-oxopentyl]amino]-3-phenylpropanoic acid

Chemical Property of N-Formylmethionyl-leucylphenylalanine

Chemical Property:

• Vapor Pressure: 7.43E-26mmHg at 25°C
• Melting Point: 271-274 °C(lit.)
• Boiling Point: 269 °C
• PKA: 3.50±0.10(Predicted)
• Flash Point: 427.7°C
• PSA: 149.90000
• Density: 1.198g/cm³
• LogP: 3.00570
• Storage Temp.: 2-8°C
• Solubility.: DMF: 50 mg/mL, clear, colorless
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 437.19844227
• Heavy Atom Count: 30
• Complexity: 567

Purity/Quality:

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

N-Formyl-Met-Leu-Phe ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-22

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)O)NC(=O)C(CCSC)NC=O
• Uses: Induces leucocyte chemotaxis, and activates macrophages N-Formyl-Met-Leu-Phe has been used for:creating gradients in Zigmond chamber chemotaxis assay performed on neutrophilsuse in neutrophil chemotaix assay anddetermination of the involvement of MAPK-activating protein kinase-2 (MAPKAPK-2) and/or p38, in the signaling pathway of human polymorphonuclear leukocytes (PMNs) stimulated by N-Formyl-Met-Leu-Phe.

Technology Process of N-Formylmethionyl-leucylphenylalanine

There total 26 articles about N-Formylmethionyl-leucylphenylalanine 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: 95.0%

2-[2-(2-formylamino-4-methylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester (285131-19-3) → formyl-methionyl-leucyl-phenylalanine (59880-97-6)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 0.333333h;

DOI:10.1007/BF02759163

Reference yield: 93.0%

N-formylmethionylleucylphenylalanine methyl ester (77543-00-1,65929-03-5) → formyl-methionyl-leucyl-phenylalanine (59880-97-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.7b02382

Reference yield: 91.0%

For-L-Met-L-Leu-L-Phe-CAM (98229-02-8) → formyl-methionyl-leucyl-phenylalanine (59880-97-6)

Guidance literature:

With sodium carbonate; In water; N,N-dimethyl-formamide; for 1.5h;

DOI:10.1016/S0040-4020(01)96451-8

upstream raw materials:

formyl-Met-Leu-Phe-OCH₂C₆H₅

For-L-Met-L-Leu-L-Phe-CAM

For-Met-Leu-Phe-OBg

2-[2-(2-formylamino-4-methylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethyl ester

Downstream raw materials:

for-Met-Leu-Phe-Lys(Phe-Leu-Met-for)-εLys(OMe)-Phe-Leu-Met-for

for-Met-Leu-Phe-Lys[γ-Asp(OMe)-Phe-Leu-Met-for]-OMe

for-Met-Leu-Phe-Lys(Phe-Leu-Met-for)-Lys(Phe-Leu-Met-for)-OMe

for-Met-Leu-Phe-Lys(Phe-Leu-Met-for)-OMe

Refernces

• 1、 Chapman, Robert S. L.,Lawrence, Ruth,Williams, Jonathan M. J.,Bull, Steven D.. "Formyloxyacetoxyphenylmethane as an N-Formylating Reagent for Amines, Amino Acids, and Peptides". supporting information. p. 4908 - 4911. Retrieved 2017/09/23.
• 2、 -. "Peptide-metal ion pharmaceutical preparation and method". . . Retrieved 2008/06/13.