EMAIL THIS PAGE TO A FRIEND
F3506 Sigma-Aldrich

N-Formyl-Met-Leu-Phe

≥97% (HPLC)

Synonym: Chemotactic peptide, N-Formyl-L-methionyl-L-leucyl-L-phenylalanine, fMLF, fMLP (misnomer but widely used)

  • CAS Number 59880-97-6

  • Empirical Formula (Hill Notation) C21H31N3O5S

  • Molecular Weight 437.55

  •  Beilstein/REAXYS Number 2315783

  •  MDL number MFCD00036780

  •  PubChem Substance ID 24894846

  •  NACRES NA.32

Purchase

Properties

Related Categories Cell Biology, Cell Signaling and Neuroscience, Chemotactic Peptides, Immune Cell Signaling and Blood, Immune System Regulation,
Quality Level   100
assay   ≥97% (HPLC)
storage temp.   −20°C
SMILES string   CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)=O
InChI   1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1
InChI key   PRQROPMIIGLWRP-BZSNNMDCSA-N
Gene Information   human ... FPR1(2357)

Description

Amino Acid Sequence

NFor-Met-Leu-Phe

General description

N-Formyl-Met-Leu-Phe is a chemotactin peptide, which functions on polymorphonuclear leukocytes (PMN), neutrophils etc.

Application

N-Formyl-Met-Leu-Phe has been used for:
• creating gradients in Zigmond chamber chemotaxis assay performed on neutrophils
• use in neutrophil chemotaix assay and
• determination 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.

Packaging

5, 10 mg in glass insert

50, 100, 500 mg in glass bottle

Biochem/physiol Actions

N-Formyl-Met-Leu-Phe induced chemotaxis in phosphoinositide 3-kinase γ (PI3K)γ-/- neutrophils, and promotes adhesion, polymerization of F-actin, Fcγ receptor-mediated phagocytosis and intracellular Ca2+ release. It acts as an inflammatory agent and activates polymorphonuclear leukocytes (PMNs) without the formation of 5-hydroxyicosatetraenoic acid (5-HETE) and leukotriene B4 (LTB4). Its effects on neutrophils and the inhibition of adenylate cyclase are inhibited by pertussis toxin.

Potent chemotactic peptide. Induces a metabolic burst in macrophages accompanied by an increase in respiratory rate, secretion of lysosomal enzymes, and production of superoxide anion.

Potent inducer of leucocyte chemotaxis and macrophage activator. Receptors that bind formylpeptides are found on phagocytic neutrophils and have recently been identified on cells of the intestinal mucosa.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number
Protocols & Articles
Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?